Author’s note: I started this post on April 22. As I write this paragraph it’s May 12. People have written books in less time. When I started this project I thought I’d have it done in a matter of days or maybe even on the same night. Here I am weeks later still hanging on Questlove’s every word and second guessing many of my selections. I’m going to leave the rest of this post the way it was when I wrote it and I didn’t know a thing about Questlove’s list and then I’ll check back in with some thoughts after my 100 have been revealed. OK, back to April 22.
Ahmir “Questlove” Thompson is my musical North Star. If he recommends it, I will likely enjoy it. I’ve been a fan since I first heard The Roots over 30 years ago. I’ve read all of his books, listen to his podcast, you name it. If Questo has done it, I’ve consumed it. I don’t agree with everything he has to say, but if he says it, I’m generally with him. Especially if Prince is involved. To me he is the world’s utmost authority on anything Prince. I would have never been insane enough to tackle an impossible task like rank my 100 favorite Prince songs and then write about them. I figured the same about Questlove. Then on April 21, 2026 – the 10th anniversary of Prince’s passing – I saw a post on Rolling Stone written by Questlove taking on that exact assignment. My first thought was, “Questlove lost his damn mind.” Then I thought, “But I definitely want to read it and make it a playlist and go on a road trip and listen to these songs in order from 100 to 1.” Then I thought, “Or, before I read this I could actually make my own Prince Top 100 list, then compare the two.” That’s how I got here.
This is intimidating. What if my Top 100 only has five of the same songs as Questlove’s? I’ll look like an idiot. But you know what else? Fuck it. My blog. My list. My opinion. I’ve only seen the first couple paragraphs of Questlove’s column. I read far enough to confirm that he did, indeed, make a top 100 list and this wasn’t some sort of clickbait to lure in suckers like me.
I’m aware that “Alphabet St.” is number 100 on Questlove’s list, so I know exactly 1% of his selections. I have a feeling his #1 song may not have even cracked my top 100. I guess we’ll find out. Here goes:
100: “Thieves in the Temple” from Graffiti Bridge (1990)
OK, I just skimmed Questlove’s list. He did some things differently than I did. I had a feeling he might because he wrote about it in the first few paragraphs, but I insisted on waiting to read the list. He added a lot of Prince side project stuff. Several songs by The Time, Vanity 6, The Family, etc. I went strictly off of Prince’s catalog, which does include his Originals album, so there are a few side project songs on it. Whatever, I’ll continue to power through. “Thieves in the Temple” did not appear on Questlove’s list. Too bad. Solid song.
99: “Family Name” from The Rainbow Children (2001)
This song is a bit of a lightning rod because of some lyrics that are understandably considered anti-Semitic. The message of the song is about slavery, lost identity, and oppression. A powerful message over a funky track.
98: “FUNKNROLL” from PLECTRUMELECTRUM (2014)
The 3rdEyeGirl era was wildly underrated and I wish they recorded more music together. Nothing but love for Donna, Ida, and Hannah.
97: “My Name is Prince” from the Love Symbol album (1992)
The early/mid-90s, hip hop-has-taken-over-and-Prince-is-struggling-to-find-his-place-and-remain-relevant-in-this-shifting-landscape era was not my favorite Prince era, but I played the shit out of this song in high school, so I had to include it here. Still a favorite of mine on any hype/workout mix I create.
96: “Sexuality” from Controversy (1981)
I imagine the “Sexuality” lyrics turned some heads in 1981. I was only five years old, so I don’t remember. Just guessing a lot of America wasn’t ready for an androgynous black man calling for “reproduction of a new breed, leaders stand up, organize” back then. Not sure they’re ready for it now either.
95: “Slow Love” from Sign O’ the Times (1987) – #71 on Questlove’s list
Questlove actually included the live version from the Sign O’ the Times Super Deluxe Edition on his list, but I’m considering it a win anyway. I finally picked one from his list! Questlove stated in his post that he’s heard at least 13 versions of this song and it makes me realize that I know nothing. I’ve heard two.
94: “Future Soul Song” from 20Ten (2010)
Prince went back to his early-80s Linn drum sound on this ironically titled song from a mostly forgotten album that I believe was only available in physical form in some European print publications. He kept it off of streaming services for years as well in his life-long battle with distributors over control of his music. It’s unfortunate that more people weren’t able to hear this one, but I respect the hell out of him fighting for his right to control how his music is distributed.
93: “When You Were Mine” from Dirty Mind (1980)
The older I get, the better Dirty Mind gets. The album – and this song specifically – live at the intersection of pop, new wave, punk, funk, and soul music from that era. An amalgam of all things 1980. When I hear it I think to myself “When You Were Mine” could’ve been performed by Huey Lewis, Devo, The Go-Gos, or about 50 other artists of that era, but it took Prince to combine them all into one.
92: “1000 X’s & O’s” from HITnRUN Phase One (2015)
A smooth, mid-tempo R&B love song from Prince’s penultimate album, released only seven months before his death. Proof there was plenty of good music in him.
91: “The Everlasting Now” from The Rainbow Children (2001)
Prince was not trying for radio play or record sales with The Rainbow Children. That’s what I like about it. Prince let go of trying to compete with the artists on the charts and got back to what he liked to call “real music by real musicians”. Too overtly religious for my taste, but still some great music on this album.
90: “Fury” from 3121 (2006)
Good song from a great album. Certainly worthy of this list. However, the real reason “Fury” is here is because of Prince’s performance on SNL in 2006. He literally set the stage on fire, then put on a guitar clinic while smirking at the camera and fixing his hair. Dude was 48 years old and still the baddest motherfucker on the planet.
89: “America” from Around the World in a Day (1985)
On “America” Prince uses funk to ask whether our country actually delivers freedom and opportunity to ordinary people. I can get on board with that. BTW, I’m literally 1-for-11 matching up with Questlove right now. That tells me two things: 1. I may have bad taste in music. 2. Prince had a lot of music.
88: “Diamonds and Pearls” from Diamonds and Pearls (1991) – #86 on Questlove’s list
This is the only song I’ve ever heard playing on three different radio stations at the exact same time. Keep in mind, this was in Green Bay, Wisconsin. It’s not like we had a plethora of radio stations from which to choose. We were waiting in line at PDQ Car Wash on the west side. “Diamonds and Pearls” came on and I wasn’t in the mood for it, so I switched stations only to find it again, then switched once more only to hear it a third time. At that point I thought the universe was trying to tell me something. Don’t turn off Prince. Oh, also, this song is gorgeous. Shout out to Rosie Gaines. “Diamonds and Pearls” is as much about her vocal performance as it is Prince. She doesn’t get nearly enough credit for her contribution here. This is a duet performed by Prince & Rosie Gaines.
87: “International Lover (Take 1 – Live in Studio)” from 1999 Super Deluxe Edition
This will be the first time I get picky. The album version is cool. I actually prefer this earlier take when he brings his vocals down out of falsetto. More conversational. Morris Day on drums. Prince on piano and vocals. He’s loose and his sense of humor comes out during the pilot’s announcements portion of the song. This version is superior. A gem and the reason why these Super Deluxe Editions exist.
86: “Lolita” from 3121 (2006)
I’ve said it several times before and I’ll say it again: 3121 is the best album of the last 25 years of Prince’s life. So many songs are throwbacks to Prince’s funky, big synth days of the early-80s. “Lolita” isn’t breaking any new ground, but it’s fun and funky as hell.
85: “Tamborine” from Around the World in a Day (1985) – #79 on Questlove’s list
Delightfully filthy and chaotic. A spicy addition right in the middle of an otherwise tame (by Prince’s standards) Around the World in a Day.
84: “Sticky Like Glue” from 20Ten (2010)
I have no idea what Prince is singing on this track, nor do I really care to look it up. I just know it’s funky.
83: “The Cross” from Sign O’ the Times (1987)
I’m not a religious person, but I’m all for it if it helps someone be a better person. I try not to let my opinion of the “religious right” taint my enjoyment of a Prince song called “The Cross”. I can still enjoy and find happiness in Prince singing about the cross being his symbol of hope. It’s uplifting. I’ll stand by that regardless of how I feel about the current state of organized religion and its influence on American politics.
82: “Alphabet St.” from Lovesexy (1988) – #100 on Questlove’s list
Once again, I’ve never paid much attention to what Prince is singing on this song other than “shake your body like a horny pony would.” I don’t care. When shit is this funky, lyrics are optional. Also, click the link above if you want to see an all-time cheesy 80s music video. A lot of bad graphics, pastel, and questionable clothing choices. Looks like a video made by the cool kids in a 1988 high school AV club. Looks like it inspired the Saved By the Bell opening credits. Zach Morris should be holding a giant cell phone in one hand and high fiving Prince with the other in the video.
81: “The Daisy Chain” from The Slaughterhouse (2004)
More filthy funk. This time from a 2001 internet-only NPG Music Club release that resurfaced as part of Prince’s 2004 collection The Slaughterhouse. Some not-so-subtle shots at D’Angelo (I assume) about “real chicken grease” in the video that I’m not a fan of, but I won’t hold Prince’s pettiness against him, as misdirected as it seems in this case. D’Angelo was making music that was significantly better and more relevant at the time. Facts. Don’t hate.
80: “WHITECAPS” from PLECTRUMELECTRUM (2014)
I dig the melancholy vibe of “WHITECAPS”. It’s the sonic equivalent of a gloomy, windy day. Hannah Welton-Ford shines on lead vocals and on drums. On the topic of Hannah: as a father of two daughters I can’t tell you how fun it is to watch someone who looks just like them sit down behind a drumset and just fucking rock. Do yourself a favor and find the video of Prince & 3rdEyeGirl at Montreux and watch them destroy for two hours. Amazing band.
79: “U Got the Look” from Sign O’ the Times (1987)
I’m only 20% of the way in and this is daunting. I thought I’d get this done in one night and that is NOT what’s happening. I’ll bet Questo didn’t have to find all of the videos and insert links and format the text and all of that junk by himself. Anyway, I don’t have a lot of rules in life, but I know this: When a song has the lyrics, “You sho nuff do be cookin’ in my book. Your face is jammin’. Your body’s hecka slammin’,” it’s automatically in my top 100.
78: “Purple Music” from 1999 Super Deluxe Edition (1982) – #94 on Questlove’s list
One of my favorite things Prince did, especially early in his career, was he’d recognize a sick groove, experiment over it, and leave it. He didn’t seem to care that popular music was supposed to fit into a 3-4 minute window. “Purple Music” is clocks in at 10:59. Never feels monotonous or repetitive. Always tinkering with something. He does go a bit overboard with the hand clap sound effect, but didn’t we all when we got our first Casio SK-1?
77: “Under the Cherry Moon” from Parade (1986) – #19 on Questlove’s list
The motion picture Under the Cherry Moon may have been a big swing and a miss, but that shouldn’t distract from the fact that we got an all-time great soundtrack out of it. The song “Under the Cherry Moon” is a lovely three minute encapsulation of what Prince was going for with the movie. Theatrical, magical, beautiful, fantastic. By the way, Questlove kind of cheated on this one and counted “New Position”, “I Wonder U”, and “Under the Cherry Moon” as “one entry composed of three songs. I do something similar later in this list (twice) but I count them as two songs.
76: “Call My Name” from Musicology (2004)
Years after Prince left the pop charts he reappeared with this gem in 2004 and deservedly won a Grammy for Best Male R&B Vocal Performance. One of the great ballads of Prince’s career regardless of era.
75: “3121” from 3121 (2006)
Some Sign ‘O’ the Times elements resurfacing on this track. The Camille voice. The disorienting, wobbly vibe reminiscent of “Dorothy Parker”. Another in a long list of great Prince songs that feel like he’s just experimenting with new toys.
74: “Rock Steady (Live)” from Indigo Nights (2008)
Prince and the NPG cover an Aretha Franklin classic and blow the roof off. Special shout out to Joshua Dunham on bass and Beverley Knight on lead vocals. This performance is the audio equivalent of a fire emoji.
73: “If I Was Your Girlfriend” from Sign O’ the Times (1987) – #11 on Questlove’s list
Prince incorporates the Camille voice and releases a song “If I Was Your Girlfriend” that has the entire world clutching their pearls because he is – yet again – taking the traditional perception of gender and turning it upside down. Behind all of the uproar is a thought provoking song about how his lover might treat him and talk to him differently if he was her female friend instead of her male friend. He knew exactly what he was doing naming it what he did, and that’s what was so brilliant about it. This is actually a pretty G-rated song by Prince’s standards early on until his queries about what she’d let him do to her go from helping her pick out clothes to…umm…other things.
72: “Uptown” from Dirty Mind (1980) – #97 on Questlove’s list
Ooh, speaking of Prince and gender fluidity, it’s “Uptown”! I swear Prince was the ballsiest dude who ever lived. He was a black man singing this in 1980. Think about that shit for a second. Incredible. Fearless.
71: “Feel Good, Feel Better, Feel Wonderful” from Lotusflow3r (2009)
I’d feel a lot better if I could get a straight answer on the name of this song. They sing “feel better, feel good, feel wonderful,” but that’s not what I’m seeing as the title of the song in some places.
70: “Future Baby Mama” from Planet Earth (2007)
I’m a sucker for a good slow jam, and Prince proved later in his career that they were light work for him. In the midst of a run of ordinary albums (again, by Prince standards) during the late-2000s/early-2010s he could still record a killer ballad. On an album that I considered mostly disappointing when it dropped, “Future Baby Mama” was the track up to the high standard I set for Prince.
69: “New Power Generation” from Graffiti Bridge (1990)
Prince’s New Jack Swing song. I still love Guy and all of that Teddy Riley stuff from this era. A lot of people overlook this album but it hit me with the exact right sound at the right age.
68: “STOPTHISTRAIN” from PLECTRUMELECTRUM (2014)
Again, I know this isn’t the groundbreaking Prince of the early-80s, but I love this anyway. Prince and Hannah signing in unison, the slow reggae vibe, the booming bass. I never skip this song.
67: “Forever in My Life” from Sign O’ the Times (1987)
I love the steady groove with the bass thumping like a heartbeat. I love the la da da da da da da da. I’m a sucker for “I need to get my shit together or I’m gonna lose this girl” songs. I’m not even 100% sure he’s singing about a girl in this song. It might be God. Probably both. Don’t care. Dope song.
66: “Soft and Wet” from For You (1978)
Not ashamed to say I knew this as an MC Hammer song long before I knew it as a Prince song. I probably should be, but I’m not. “Soft and Wet” came out when I was 2. Hammer was everywhere when I was in high school. Seems like a solid excuse.
65: “Something in the Water (Does Not Compute)” from 1999 (1982) – #42 on Questlove’s list
Man, I’m in shock right now. I was steeling myself for an argument why I have this song so low on my list compared to Questlove. Prince heads love this track. It’s only #42 on his list. WTF?!??! I would’ve bet this would be in Questo’s top ten. What a wild song. That beat. The fact that there’s not really a melody at all. Just noises.
64: “Billy Jack Bitch” from The VERSACE Experience (1995)
Prince leaning into his petty side and attacking a gossip columnist who he felt took it too far and was lying, mocking, and embarrassing him. You know that columnist must’ve been like, “Got him! He just wrote a song about me.” Or she sued him. I genuinely don’t wanna know. Kind of pissed Prince let her get under his skin and gave her the time of day. Still, I dig the results. I ride for “Billy Jack Bitch”. Literally. I love listening to this song in my car. I prefer the Versace version over the Gold Experience version. The tempo and key are cranked up slightly giving it more energy. However, if you really want to ride with it the Gold Experience version is twice as long.
63: “The Dance Electric” from 1999 Super Deluxe Edition (1982) – #30 on Questlove’s list
Questlove included the André Cymone version of this song on his list, but again, I only put songs from Prince albums on this list. Prince’s version and Andre’s version are essentially the exact same song anyway. Crazy that Prince recorded the song in 1982 but Cymone released it three years later and it still sounded like it was from the future.
62: “Clouds” from Art Official Age (2014)
The song that introduced me to Lianne LaHavas. Deserves a spot on the list just for that. It helps that it’s wildly funky. When good musicians say things like, “The funk lives in the spaces between the notes,” I think of this song. The pauses feel longer than they should and everything feels behind in all the best ways.
61: “Dark” from Come (1994)
Most of what I’ve read dismisses Come as a throwaway Prince album, but it’s actually one of my favorite Prince albums to own on vinyl. The whole thing is a vibe different from anything Prince had done before. A cool listen from start to finish. “Dark” is my favorite track on in the collection. Bluesy and laid back.
60: “Beautiful, Loved, and Blessed” from 3121 (2006)
At this point you’re probably thinking 3121 is my favorite Prince album. I swear it’s not. It just had enough good tracks to scatter throughout the bottom 40% of this list. “Beautiful, Loved, and Blessed” is a lovely slice of positivity. Prince protégé Tamar sings beautifully. The real magic in this song happens – once again – during the SNL performance. At first Prince seems content to let Tamar shine, but Tamar cranks her performance up to 11 and Prince has no choice but to meet her at that level with one of my all-time underrated Prince moments. They share a fantastic final chorus together before Prince and the band unleash some funk that scorches Studio 8H.
59/58: “I Would Die 4 U” and “Baby I’m a Star” from Purple Rain (1984) – “I Would Die 4 U” #40 on Questlove’s list
Questlove included an unreleased 30 minute version of “I Would Die 4 U” in his list that I need to check out immediately. I can’t separate these two songs. I can’t have one without the other. That said, “Baby I’m a Star” is better. That’s officially #58 if anyone is keeping track. I tried to get my oldest daughter, Phoebe, to dance to a Prince song at her dance showcase her senior year and when she refused to choreograph a routine to “The Beautiful Ones” I suggested “Baby I’m a Star”. I was curious to see what she’d do with a song at that tempo. She chose “Feeling Good” instead. Maybe I can get Lucy to do it in a few years when it’s her turn.
57: “How Come U Don’t Call Me Anymore (Take 2)” from 1999 Super Deluxe Edition (1982) – #56 on Questlove’s list
Another confession: I knew this as an Alicia Keys song before the Prince version. I didn’t get to know Prince B-sides until I got older, got a little money, and the internet existed. I dig “Take 2” because it’s longer and gives Prince more time to mess around. At the risk of offending my fellow Prince heads, my favorite performance of this song came during Alicia Keys Unplugged when she unleashes a vocal explosion so impressive it literally leaves me in tears anytime I hear it for reasons I can’t explain.
56: “Let’s Work” from Controversy (1981) – #69 on Questlove’s list
If you were listening to this song in 1981 you were the coolest person your friends knew. Well done.
55: “Emotional Pump” from Sign O’ the Times Super Deluxe Edition (1987)
I hesitated to put a 40-year-old track that sat unreleased until six years ago this high on the list, but damn this song is dope. I don’t love the melody, but that bass line more than makes up for any flaws. Apparently this song was written for Joni Mitchell and she turned it down. What the hell would that have sounded like? I’m not all that familiar with Joni’s work, but this doesn’t seem like her vibe.
54: “Take Me With U” from Purple Rain (1984) – #47 on Questlove’s list
Yeah, every song from Purple Rain made the list. Easily. This song might get dismissed as a trifle. Apollonia isn’t an A+ singer. Whatever. My wife and I burned a mix CD for everyone who attended our wedding and this song was on it. We play it on every road trip. It makes me happy, especially when Apollonia says, “Thank you!”
53: “The Question of U” from Graffiti Bridge (1990) – #50 on Questlove’s list
A haunting ballad that sounds like a leftover from the Under the Cherry Moon era. A hell of a leftover.
52: “Feel U Up” from 1999 Super Deluxe Edition (1982)
Can you imagine if the internet existed in 1982? What if Prince was actually able to release as much music as he wanted, when he wanted back then? There are so many levels to Prince’s 80s music output. There were albums, B-sides, side projects, songs given to other artists, and songs that just sat in the vault for decades. How many more classic albums would Prince have? This song rotted in the vault for damn near 40 years, then just appeared like, “Here, people. Some more amazing shit Prince made back in the day. Enjoy.” I know hardcore Prince heads knew about songs like “Feel U Up” loooong before the Super Deluxe Editions came out, but I didn’t. I didn’t want to listen to shit that he didn’t intend for us to hear. Something felt unethical or dirty about it. Like I was snooping around somewhere I wasn’t supposed to be. Now I realize I may have missed out on half a lifetime of incredible music.
51: “Gigolos Get Lonely Too” from Originals (2019)
First off, of course I’m aware that this is a track from The Time’s 1982 album What Time Is It? Since it’s on Prince’s 2019 Originals album, it qualifies. This song is the rare occasion when there’s a version with Prince’s vocals and a version with someone else’s and I prefer the other person’s. Morris Day kills this minimalist 80s slow jam about feeling empty after lots and lots of meaningless sex.
50: “Delirious” from 1999 (1982) – #38 on Questlove’s list
Not sure how I feel about rockabilly as a genre, but I can tell you this: If Prince programmed the drums like this on more rockabilly music, I’d listen to more of it.
49: “Musicology” from Musicology (2004)
The one time I got to see Prince in-person was Summerfest 2004 on the Musicology tour. This song holds a special place in my heart. My, “Oh shit, Prince is back!” moment.
48: “Power Fantastic (Live in Studio)” from Sign O’ the Times Super Deluxe Edition (1987) – #27 on Questlove’s list
A magical song about the fusion of love, inspiration, and emotion made more special on this “Live in Studio” version as you can hear Prince directing his band – scattered throughout his house/recording studio – from the booth. A moving track and peek into Prince’s interaction with The Revolution shortly before their breakup.
47: “D.M.S.R.” from 1999 (1982)
If we’re at a party or a club or a bar or anywhere (which doesn’t happen often anymore because I’m 50) and this song is on and you’re not dancing you can kindly get the fuck out of my sight.
46: “Sexy M.F.” from the Love Symbol album (1992)
Anytime I think Prince’s confidence took a hit and he lost step during the early years of hip hop I only need to hear this song. Prince may have taken some time to adapt to the new hip hop/R&B landscape, but the guy who wrote and recorded “Sexy Motherfucker” was not lacking confidence.
45: “The Glamorous Life” from Originals (2019) – #12 on Questlove’s list
8-year-old me didn’t know this was a Prince song. I just saw a pretty girl playing the shit out of the drums and thought it was cool. I was right.
44: “I Feel For You” from Prince (1979) – #7 on Questlove’s list
For the record, Chaka Khan’s version of “I Feel For You” is the one that made Questlove’s list. Once again, 8-year-old me just thought this was a cool ass song. I wasn’t aware that it was a Prince cover or that there was a Stevie Wonder sample involved. In fact, the first time I heard Prince’s version my reaction was, “Oh, Prince covered that Chaka Khan song?” Your preference is likely tied to taste. Chaka’s version is very 80s. Prince’s is more timeless. I’ll take either.
43: “Elephants & Flowers” from Graffiti Bridge (1990)
I know, this is a lot of Graffiti Bridge. I was 14 when that record came out and it was right in my wheelhouse even though the movie is…how do I put it politely? Not great. Easily my favorite scene is when The Kid and the NPG are performing “Elephant & Flowers” in an amazing club for exactly eight people who are losing their minds. What the hell is wrong with the people in this town? The Kid is playing live, there’s no line at the bar and plenty of room on the dance floor. Where is everyone? I want a time machine so I can go back to 1990 and be the ninth person at Glam Slam that night. It looks amazing. These are the same idiots from Purple Rain who were rolling their eyes while The Revolution was destroying “Darling Nikki” at First Avenue. Everyone in that town sucks except for The Kid, the NPG, and those eight maniacs at Glam Slam.
42: “I Could Never Take the Place of Your Man” from Sign O’ the Times (1987)
I love the storytelling in this song. Prince meets a girl at the bar. She needs a man. He just wants some sex. He knows he can’t be what she needs and tells her not to waste her time. Some of my favorite Prince songwriting.
41: “Anotherloverholenyohead” from Parade (1986) – #90 on Questlove’s list
I love the “Next Steps” songs in Prince’s storied career. You’re not gonna find “Anotherloverholenyohead” on a greatest hits collection, but anytime a streaming service has the Next Steps playlist that’s where you’ll find songs like this. Maybe a little too weird for radio, but real shit the hardcore Prince fans love. Show me someone who loves this song and I’ll show you someone who gets Prince on a deeper level.
40: “I Wanna Be Your Lover” from Prince (1979) – #15 on Questlove’s list
“I Wanna Be Your Lover” is Prince’s equivalent to “Rock With You” by Michael Jackson. Look at the videos. Michael’s is literally shinier. Prince’s is gritty. I wasn’t old enough in ’79 to know, but from what I gather this song was a lot of people’s introduction to Prince. If you want peak awkwardness from Prince, check out his American Bandstand appearance in 1980. The performance is the typical AB lip-sync, but stay for the post-song interview. It will not disappoint.
39: “Breakfast Can Wait” from Art Official Age (2014)
A funky slow jam with a wink to Dave Chappelle. The Camille voice near the end went way too far and crossed over into Alvin and the Chipmunks territory, otherwise this song is pretty flawless. Still one of Prince’s best tracks this century.
38: “Wonderful Ass” from Purple Rain Super Deluxe Edition (1984)
The first time I heard “Wonderful Ass” the melody sounded so silly I laughed out loud. I wasn’t laughing three minutes later when I was nodding my head to it. The funk in “Wonderful Ass” sneaks up on you. Also, I love the “pros and cons list” theme to the lyrics. On the negative side, you’re jealous, you’re aggravating, you think I’m neurotic…but, on the other hand, that ass.
37: “Joy in Repetition” from Graffiti Bridge (1990) – #35 on Questlove’s list
What I love most about this song is that “Joy in Repetition” is not just the title. Prince makes you feel it.
36: “She’s Always in My Hair” from “Raspberry Beret” single (1985) – #74 on Questlove’s list
Considered by many to be the peak of Prince’s legendary B-sides. Not at the top of my list, but still a classic. This is also peak brutal honesty in songwriting. You’re incessantly supportive and it’s actually annoying. Maybe I’ll marry you. Maybe I won’t. Ouch.
35: “Gett Off (Damn Near 10 Minutes)” from Diamonds and Pearls Super Deluxe Edition (1991)
“Gett Off” was a single from the album Diamonds and Pearls released in 1991, but the “Damn Near 10 Minutes” version was 12″ promo single originally for DJs. As a rule, the long versions of Prince songs are almost always better. Almost. We’ll get to that later. In this case, Prince talks a lot of shit on the 10 minute version that you don’t get on the album. I once heard Questlove say that the best rapper on Prince’s albums was Prince. I completely agree. “Gett Off” is exhibit A.
34: “Dreamer” from Lotusflow3r (2009)
“Dreamer” is one of those late-era Prince tracks that makes me wonder how it would’ve performed on the charts if he’d released it during a different period of his career. I have a feeling “Dreamer” is a #1 hit for him the 1980s or even early-90s. It was nominated for a Grammy for Best Solo Rock Performance but I don’t know too many people who were listening to it. Prince had so many genres in his bag and he had the ability to weave them together into their own thing. Prince was his own genre, but on “Dreamer” he just rocks, and it’s outstanding. When I first heard it I actually thought it was a Hendrix cover. Nope. Just 50-year-old Prince shredding.
33: “Let’s Pretend We’re Married” from 1999 (1982)
1999 is my favorite Prince album primarily because it’s Minneapolis sound from start to finish and I love that vibe. The same reason I love The Time’s albums. “Let’s Pretend We’re Married” is Prince at his filthiest, but also peak Minneapolis-sound.
32: “Pop Live” from Around the World in a Day (1985) – #57 on Questlove’s list
I was disappointed in “Pop Life” when it was released 40 years ago. Also, I was nine years old. There’s no shortage of old Prince lyrics that make me cringe. In fact, a lot of them are on this list. This is the opposite. “Pop Life” seems exponentially more relevant in the age of influencers, viral content, reality stars, etc. A timeless ode to emptiness found in fame.
31: “Black Sweat” from 3121 (2006)
My favorite Prince song of this century. Period.
30: “Irresistible Bitch” from 1999 Super Deluxe Edition (1982) – #52 on Questlove’s list
Point of clarification: The version Questlove is referencing on his list is the B-side to the “Let’s Pretend We’re Married” single. The version I prefer is an alternate take that was officially released as part of the 1999 Super Deluxe Edition in 2019. The alternate version I’m referencing is the yang to the B-side’s yin. The 1983 B-side version is more spoken word and…cold? Robotic? The alternate version features Prince screaming most of the lyrics. It feels like it could be a Time song, musically. I dig both, but the two versions couldn’t feel more different, and I prefer the alternate.
29: “Electric Chair” from Batman (1989)
Batman was the biggest thing in the world in the summer of 1989 and “Batdance” was everywhere. My favorite part of the song was when it gets funky as hell in the middle and Prince is singing about Vicki Vale. He sings, “If a man is considered guilty for what goes on in his mind then give me the electric chair for all my future crimes.” Then I got the album and it occurred to me that “Electric Chair” is its own separate, far superior song.
28: “Controversy” from Controversy (1981) – #14 on Questlove’s list
“Controversy” is a funky, PG-rated, 7-minute synopsis of Prince’s first four albums with the Lord’s Prayer in the middle.
27: “Sex Shooter” from Originals (2019)
I’m not sure I believe in guilty pleasures. If you like it, why feel guilty about it? That said, it’s hard to justify how much I love this idiotic song. “Sex Shooter” was originally performed by Apollonia 6 in Purple Rain and the opening track on Apollonia 6’s self-titled album, but good luck finding it on any streaming services. I was quietly thrilled when I discovered that it would be included as part of the Originals album so I could hear Prince’s version. I’m aware of the absurdity of the lyrics. I don’t care. Prince could put pretty much anything he wanted over that beat and I would dig it…and that’s kind of what he did. Inane lyrics. Peak Minneapolis sound.
26: “Nothing Compares 2 U” from Originals (2019) – #16 on Questlove’s list
Unpopular opinion time: I hated this song when the Sinéad O’Connor version was popular. If it popped up on the radio or MTV I couldn’t shout out, “Change that shit,” quickly enough. The word melodramatic doesn’t even begin to describe how I feel about O’Connor’s performance. Then I heard Prince’s live version with Rosie Gaines on The Hits compilation and it was a major improvement, but it’s still not working for me. Then I heard The Family’s version of it that was actually released in 1985 – five years before O’Connor’s – and it still wasn’t quite there. Questlove chose The Family’s version for his list, but it’s a little heavy on organs and light on drums for me. Then I heard Prince’s version on the Originals album. Just right.
25: “Money Don’t Matter 2 Night” from Diamonds and Pearls (1991) – #46 on Questlove’s list
Add another one to the list of Prince songs that are more relevant now than ever. In fact, Prince was such a prophet that a clip of Donald Trump appears the first time sings, “that’s when you find out that you’re better off making sure that your soul’s alright.” Nailed it. “Money Don’t Matter 2 Night” is a timeless song in the middle of an album that sounds very 1991 otherwise.
24: “Sign O’ the Times” from Sign O’ the Times (1987) – #60 on Questlove’s list
Part of what made Prince so brilliant was that he could transform more quickly and effectively than anyone. JAŸ-Z said “We off that, is you still on that?” on his 2009 track “Off That“, and that’s how I think of 1980s Prince. Oh, you dug 1999? I’m already on Purple Rain. You really loved that? Here’s Around the World in a Day. OK, it took you a minute to catch up to that, now here’s Parade. You still with me? Here’s Sign O’ the Times. Just when you thought you had Prince figured out, he’d shift into something else. The first time I heard “Sign O’ the Times” I was only 11 years old but even at that age I was like, “Wait, Prince sounds like this now???” He never settled…but he was always funky. Damn, the bass line on this song.
23: “Automatic” from 1999 (1982) – #39 on Questlove’s list
That drum machine. Goddamn. The first six seconds of “Automatic” might be my favorite. So much cool shit going on in this song, but that beat is so tight the rest is secondary. Who else in the history of music could’ve pulled off this song? Bowie? Maybe. Funk from the future. I’m not sure I ranked “Automatic” high enough…
22: “Housequake” from Sign O’ the Times (1987) – #32 on Questlove’s list
When my kids were little I didn’t want them cursing and I definitely didn’t want them telling anyone to “shut up” because I find that more offensive than swearing at someone. However, there was always one exception: “Housequake”. You haven’t lived until you have your three little kids in your car and Prince yells, “Question: Does anybody know about the quake?” and you hear three little voices reply, “BULLSHIT!” from the backseat. Actually, two little voices. Lucy is 15 now and I still haven’t heard her curse once. She refuses. I admire and respect it. So would Prince. Little Phoebe and Andy, however, could sniff out “Housequake” from a mile away and were always ready with, “Shut up, already. Damn!” before the track even started.
21: “Head” from Dirty Mind (1980) – #31 on Questlove’s list
When people ask me if they’ll like Game of Thrones (the show, not the books) I tell them to watch the first episode. If they enjoy that, they’re good. There’s a beheading, there’s some incest, there’s a lot of blood and death. It’s a baptism by fire. I’d say the same about anyone asking me if they’d like Prince. If they dig “Head”, they’ll be fine. If it’s too much, they should just play “Purple Rain” and not dig any deeper. Dirty Mind was Prince unleashed, and “Head” is the filthy funk masterpiece that announced his arrival.
20: “Jungle Love” from Originals (2019) – #65 on Questlove’s list
Seems blasphemous to say that “Jungle Love” is from 2019’s Originals album. The real ones know “Jungle Love” comes from The Time’s Minneapolis masterpiece Ice Cream Castle. You want a party wherever you are? Your car. The office. A funeral. No matter. Press play on “Jungle Love” and start a dance party. If you don’t dig “Jungle Love”, we can’t be friends.
19: “Xtraloveable” 1982 Demo
Easily the most controversial entry to the list. This is my holy grail. Maybe because it’s forbidden fruit…or maybe because it’s an amazing song that, unfortunately, contains one gigantic elephant in the room. I’ll try to keep this brief. “Xtraloveable” is one of Prince’s best beats of that era. A surefire hit if he had released it. It’s a fun track until the very end when he declares that he wants this woman so badly that he might have to rape her. It’s chilling. It also happens five minutes into the song. Not trying to excuse it, but it seems like an easy fix. Fade that shit out early, we get our song, nobody gets hurt. In 2015 Prince released a completely re-recorded version of “Xtralovable” for HitNRun Phase 2. It’s a super shiny, polished version of the 1982 vault classic. It’s fine. It removes all of the nastiness of the original, which is both a good and bad thing. When the 1999 Super Deluxe Edition was released in 2019 with 24 previously unreleased vault tracks from the era I was certain I’d finally get the real version. It wasn’t included. The estate said something to the effect of, “The official version was released in 2015,” and they have no intention of giving us the original in its cleaned up, remastered glory. Looks like I may never get my wish. The 1982 version of “Xtraloveable” remains vaulted.
18: “Adore” from Sign O’ the Times (1987) – #23 on Questlove’s list
Questlove said that “Adore” haunts him because it represents the end of the Revolution era. For the past 11+ years I’ve felt exactly the same about the final track on D’Angelo’s final album: “Another Life” from Black Messiah. The first time I heard that song (and every time since) I was acutely aware of the fact that it may be the last time I got the opportunity to hear a new D’Angelo album for the first time. It haunts me even more now that he’s gone and I know I was right. The song I compared “Another Life” to: “Adore” by Prince. I even wrote about it. I just blew my own mind.
17: “Erotic City” from “Let’s Go Crazy” single (1984) – #26 on Questlove’s list
When I was in college our favorite dive bar had a jukebox. Every Tuesday night you could buy a cup for $2 and then they had a local beer that was only 25 cents a cup. I’m not a beer drinker so I was drinking 7&7’s or amaretto sours like I was fucking Rockefeller, but our group of friends would fill that bar every week and have a blast getting drunk for under $5. The jukebox had a limited selection and our go-to when we got too drunk and just wanted to bro out, put our arms around each other, and sing together was “Paradise City“. However, that glorious jukebox also had a CD in it of songs inspired by George Clinton or P Funk or something. I don’t remember specifics. It was 25 years ago and I wasn’t sober. Every single Tuesday nightg we’d play “Bop Gun” by Ice Cube and “Erotic City” by Prince. Good times. I should try to find that CD…
16: “Purple Rain” from Purple Rain (1984) – #8 on Questlove’s list
If you’re looking for tiers, we just hit the top tier. On any given day any song from here to the end could be my #1. How is “Purple Rain” this far down? I can’t shake the comparison to “Faithfully” by Journey. On my personal musical spectrum, Prince and Journey couldn’t be much further apart. Yet here’s Prince playing arena rock at least partially inspired by the likes of Journey and Bob Seger – two acts that I have little interest in and no desire to explore further. “Purple Rain” is gorgeous and amazing because it’s Prince, but a 9-minute power ballad was never going to be the #1 song on my Prince list.
15: “Partyup” from Dirty Mind (1980)
Questlove wrote that he often skips “Purple Rain” because it’s the last song on the Purple Rain album and the movie ends on “Baby I’m a Star”, so that feels like the completion of the album. For the longest time I would skip “Partyup” – the final track on “Dirty Mind”. Then when Prince passed away, SNL aired a special tribute episode and played all of his performances on the show, starting with “Partyup” in 1981. It was so raw and electric I watched it nonstop for about a month. I no longer skip it. In fact, it’s become my favorite song on the album.
14: “7 (Acoustic Version)” from “7 (Single)”
Big caveat here: I has to be the acoustic version. The album version is wonderful, but would fall further down the list. The acoustic version strips away the obvious early-90s sound and gives “7” a timeless feel. It loses the hip hop drums, the DJ scratching, and the weird laughing. That’s not something I’d usually recommend as I love early-90s hip hop, but I don’t need it mixed with this track. What we’re left with is an acoustic guitar, some light percussion, and Prince’s vocals. It’s so much more powerful. The day after Prince died I was driving around with Prince on shuffle and this version of “7” punched me right in the heart. I can take you to the exact spot on Taylor Street where I began uncontrollably weeping to this song wondering what the hell was happening to me. First time I remember a song moving me to tears. It happens all the time now because I’m a 50-year-old sap, but the acoustic version of “7” did it to me first.
13: “Let’s Go Crazy (Special Dance Mix)” from Purple Rain (1984) – #25 on Questlove’s list
The movie Purple Rain is a mixed bag. Unlike the soundtrack, it’s far from perfect. The first ten minutes of that movie are the greatest first ten minutes in the history of film. I didn’t actually see the movie until I was much older, but I saw the video for “Let’s Go Crazy” when I was 8 years old. All I wanted to do was be in First Avenue alongside those people going crazy with Prince. It’s still all I want to do. A kick ass band at a smoke filled club full of drinking and cool people. If heaven exists I hope it’s First Avenue in Minneapolis while The Revolution plays “Let’s Go Crazy”. Also – for the second consecutive song – I’m going to get picky. I need the special dance mix. The album version is dope, but the special dance mix is the one The Revolution plays in the movie. I need the 7:36 version. Why? Because three more minutes of “Let’s Go Crazy” is obviously better. If “Let’s Go Crazy” is playing and I hit the fork in the road at the 3:10 mark when you find out if you’re getting the album version or the special dance mix, I better hear the fucked up piano solo. My energy level actually rises. Like caffeine for my soul. I need those three minutes.
12: “Darling Nikki” from Purple Rain (1984) – #64 on Questlove’s list
Seriously, Questlove, this idea is ridiculous. It’s impossible to rank these songs. “Darling Nikki” shouldn’t be #64 or even #12 on any list ever. Too low. Yet here we are. You know how I know Prince was the baddest motherfucker who ever walked this earth? In 1983 he wasn’t even a household name – if he was, just barely – yet somehow he talked himself into a major studio film. When it was time to turn in the music for the movie he handed them “Darling Nikki” with a straight face. A song about a wild sexual encounter that sounds like nothing else before or since, the last 50 seconds of which are a hymn played backwards declaring that the Lord is coming. And now it’s smack dab in the middle of the greatest soundtrack ever recorded. The performance is one of the best scenes in the movie. Literally unbelievable. How did that movie happen?
11: “Sometimes it Snows in April” from Parade (1986) – #22 on Questlove’s list
“Sometimes it Snows in April” takes me to places I don’t always want to go. Prince passed away in April. D’Angelo performed it on the Tonight Show as a tribute to Prince in April of 2016, and now D is gone as well. Three years later my dad passed away in April. “Sometimes it Snows in April” isn’t a song I listen to in my car or when I’m hanging around with my friends. It’s a song I listen to in the dark with a drink in my hand. When I am able to enjoy it it’s a beautiful, melancholy ride. It’s just not everyday music. In fact, it’s not music at all. It’s sonic catharsis.
10: “17 Days” from “When Doves Cry” single (1984) – #78 on Questlove’s list
It’s a damn shame that Prince never found a spot for “17 Days” on one of his albums. Of all the legendary B-sides in Prince’s vast repertoire, this is the one that would’ve been a smash hit. The B-sides were mostly a chance for Prince to showcase his experimental side, but this one could’ve been a chart-topper in 1984 or ’85. Catchy melody and even catchier lyrics. “Here I sit in my lonely room looking for my sunshine. All I’ve got is two cigarettes and this broken heart of mine.” Outstanding. A timeline exists where Prince releases “17 Days” as a single and it ends up on every Prince Greatest Hits compilation that follows. Instead it’s an unknown only celebrated by the fanatics like me.
9: “1999” from 1999 (1982) – #5 on Questlove’s list
I’m sure I’ve written about this more than once, but here goes again. I was six years old when I first heard and saw the video for “1999”. SIX! I remember sitting on our living room floor on Johnson Street watching America’s Top Ten with Casey Kasem and he introduced “1999”. It’s a concert video – all of Prince early videos were concert videos that look like they could’ve been performed in a local high school auditorium. There were some pretty girls (Lisa Coleman and Jill Jones) and a dude who I swore was Rod Carew (Dez Dickerson. Hey, I was six and had never seen a black person, so every dude I saw on TV looked like a baseball player to me. What can I say?) and a guy dressed like a doctor for some reason. Then this badass with a sparkly purple trench coat and pompadour came sliding down a fireman pole into the song and stole my heart. Forever. It took less than a minute for Prince to win me over. Again, I was six. How many things (not including family) do you still love at 50 that you loved when you were six? Oh, and the song? Do you know how many times my little ass sat in the backseat of our station wagon daydreaming about Prince literally having a lion in his pocket? Or the sky being purple with people running everywhere? Or Prince having a dime and using it to play “1999” in a jukebox while all of this other shit was happening? Why are these people fighting for their lives anyway? I didn’t know, but I loved it and I still do. Lastly, shout out to the last half-minute of “1999” for being, quite possibly, the funkiest 30 seconds of music in recorded history.
8: “Computer Blue (Hallway Speech Version)” from Purple Rain Super Deluxe Edition (1984) – #85 on Questlove’s list
I’ve recently (finally) started digging into Fela Kuti’s catalog. Fela routinely made songs 10+ minutes long. In an interview on the Fela Kuti: Fear No Man podcast I heard one of his bandmates say that he would sometimes let a song build up for 5-6 minutes before any lyrics so the groove could put people in a trance. That’s my favorite kind of music. And while it only takes a few seconds for Lisa to ask Wendy if the water is warm enough in “Computer Blue”, I believe the concept is similar. When a groove is this good you’ve gotta let it play out for at least ten minutes and see what happens. “Computer Blue” is Prince throwing the entire kitchen sink at a song. Linn drum: A+. Prince’s vocals: A+, especially on the second verse, which you don’t get to hear on the album version. Keyboards: A+. Guitar: A++, especially the guitar solo at 5:26. Chef’s kiss on “Computer Blue”. The sound of a true genius expanding his horizon.
7: “Mountains” from Parade (1986) – #59 on Questlove’s list
One night about eight years ago on the Tonight Show Jimmy Fallon quizzed Questlove by playing him one-second clips of Prince songs and having him guess what song it was. I wish I could find that clip online, but of course every link I can find is dead. I recall doing just as well as Questlove, but the moment that stands out in my memory is when Jimmy played the first second of “Mountains” and Questo identified it immediately (as did I, for the record). Jimmy was like, “How do you know that? I’ve never even heard of that song.” I was like, “Oh poor, sweet Jimmy Fallon. You fool. That sound you hear is a million Prince fans yelling, “What?!? This dude doesn’t know ‘Mountains’???” No, “Mountains” is not one of the so-called Prince essentials, but it’s the song you’ll find on every “next steps” list. A dreamy track about overcoming obstacles in the name of love and hope. If you’re the kind of person that likes Prince’s popular stuff but finds some of his more adventurous lyrical content off-putting and need a song to offset the nastiness of “Head” or “Darling Nikki” and “Beautiful, Loved & Blessed” wasn’t doing it for you, “Mountains” certainly will.
6: “Kiss” from Parade (1986) – #17 on Questlove’s list
Damn, Parade is a good fucking album. Popular opinion seems to be that Sign O’ the Times is Prince’s best album. Some say Purple Rain. A few say 1999. Some say Dirty Mind. Sitting right there in the middle of that run getting less love but making its own claim is Parade. I’ve written about a lot of Parade’s songs on this post, but the one thing it hasn’t had is a radio hit. Enter “Kiss”. It’s so ubiquitous at this point I take it for granted. Prince spent the better part of a decade doing wild shit never heard before, then hit us with “Kiss”, a stripped-damn-near-bare funk masterpiece that leaves behind all of the chaos of a song like “Computer Blue”. However, here’s where Questlove and I part ways and I contradict myself: While my rule is almost always more is better, that is not the case with “Kiss”. The album/radio version of Prince ends on a tantalizing guitar riff that fades to silence. I spent years fantasizing about the glorious funk that existed after that fade. When I finally found out…what a disappointment. It’s another one of those Prince songs that sounds like he got a bunch of new toys, but unlike most of them, “Kiss” turns into chaos, and not in a good way. I’ll only say this once about a Prince song: Stick with the 3:46 version of “Kiss”. You don’t want or need to hear the extended version.
5: “Raspberry Beret” from Around the World in a Day (1985) – #29 on Questlove’s list
My 15-year-old daughter Lucy is a Billie Eilish fanatic. I love everything about this. It tells me so much about her. I can’t ask for a better role model for my kid than Billie. I’m a big fan myself. Lu’s love of Billie tells me that she appreciates good songwriting. During many long car rides Lucy and I have broken down Billie’s lyrics together. Then I get to do that old dad thing where I play her a Prince song and say, “Listen to what Prince did here.” I’ll play her “Raspberry Beret” and say things like, “He didn’t just say he was bored, he said he was busy doing something close to nothing, but different than the day before.” He doesn’t say she was dumb. He says, “Overcast days never turned me on, but something ’bout the clouds and her mixed.” He doesn’t say they had sex in a barn. He says, “The rain sounds so cool when it hits the barn roof and the horses wonder who you are. Thunder drowns out what the lightning sees, honey you feel like a movie star.” He wasn’t just a musician. He was a poet and a raconteur. He’s not just singing a song or playing music, he’s painting a colorful picture. I think Lucy appreciates that. Or she excels at acting interested to make me feel good. Regardless, comparing Billie Eilish to Prince is about the highest compliment I can give, but I believe she’s worthy of it.
4: “When Doves Cry” from Purple Rain (1984) – #3 on Questlove’s list
When I talk music I’m constantly attempting to explain my take that someone’s best song and my favorite song can be two different things. In my opinion, “When Doves Cry” is Prince’s best song. It’s Prince at his most Prince. Much is made of the lack of bass on this song, but there’s a reason. It was unheard of. Who just removes the bass? Motherfucking Prince, that’s who. The result is an ice cold ode to the death of love. Going back to my Lucy songwriting conversations, this was also lesson one. Another artists could’ve easily called this song “When Love Dies”. Same message. Same number of syllables, so it’s a logical substitute. Instead we get “When Doves Cry”. Such a poetic way to put it. Absolutely one of the greatest – if not the greatest – songs of my lifetime. It’s just not quite my favorite.
3: “Little Red Corvette” from 1999 (1982) – #1 on Questlove’s list
One more thought on Prince’s lyrics. Quite often while perusing Threads, someone (or some bot?) asks, “What’s the best opening line in music history?” I always make a point to answer, “I guess I should’ve known by the way you parked your car sideways that it wouldn’t last.” Just sit and think about that shit for a second. I’ve heard the song so many times it’s easy to just take songwriting like that for granted and let it go in one ear and out the other, but really think about it. How did Prince dream up that line? One of those moments where you’re not sure what he’s talking about yet, but you also know exactly what he’s talking about at the same time. I’ve been listening to this song consistently for 43 years (believe it or not, the 45 of “Little Red Corvette” was the first record I ever owned…thanks mom!), and it still blows me away. Did he write that down in his notebook on the first try, or did he get further into the song and the Corvette concept and then came back to the beginning like, “This would be a clever way to start the song”? I didn’t know what Prince was actually singing about many years later, but I need to thank Prince. If he had just written about an encounter with a more experienced sexual partner instead of a sports car, my mom would’ve never purchased the record for a fascinated six-year-old boy and who knows what happens with me and Prince after that?
2: “The Ballad of Dorothy Parker” from Sign O’ the Times (1987) – #24 on Questlove’s list
Let me say this first: I’m not intentionally picking songs that aren’t hits at #1 and #2 because it makes me feel more credible or because I feel some need to prove to the world or anyone reading this that I’m a Prince fan on a deeper level than most. “Dorothy Parker” is sincerely my second favorite Prince song. In fact, I have often said that I don’t have one favorite Prince song and they’re 1a and 1b, but if Questlove could make a top 100 without having ties, I will too. I chose my #1 song (which I’ll keep a secret like it’s some big reveal you haven’t already skipped ahead to or can’t see about two inches down this page) over “Dorothy Parker” for one reason: It’s bigger. “Dorothy Parker” is niche. It’s the opposite of “Purple Rain”. It doesn’t have a melody. It sounds…wobbly? Prince’s engineer, Susan Rogers, recalled this recording session on a podcast. I’ll attempt to accurately summarize. Prince had just built a recording studio in his brand new house and he couldn’t wait to make music there. Rogers didn’t have everything setup correctly when Prince recorded “Dorothy Parker” and when she realized how it sounded she thought he might fire her. She thought she ruined the whole session. Instead he dug it and decided to roll with it. Their happy accident worked perfectly and I can’t believe this sound wasn’t intentional. I had an epiphany just now reading Questlove’s thoughts on “Dorothy Parker” that might explain why I love it so much. He said, “Good people, please welcome ‘Neo Soul’!” Goddamn it, he’s right. “Dorothy Parker” is neo soul eight years before I ever heard of D’Angelo. A revelation that explains my deep love for this song. “Dorothy Parker” isn’t just a song, it’s a vibe. The best vibe. Dorothy Parker was cool.
1: “The Beautiful Ones” from Purple Rain (1984) – #4 on Questlove’s list
I was hoping Questo would give me a nugget about “The Beautiful Ones” that would explain to me why I love it so much the same way he did with the neo soul comparison to “Dorothy Parker”. Instead he just blew my fucking mind all over this desk. More on that in a second. How does one describe the dark beauty of artwork like “The Beautiful Ones”. First, I believe to fully understand it you need to stop reading and watch this:
The visuals add to the experience. Prince, bathed in purple light, baring his soul on stage to a stunning Apollonia in front of his rival, Morris Day, and a crowd of fans. I don’t think anyone in the Purple Rain cast was a threat to be nominated for any acting Oscars – the least likely being Apollonia – but she knocks this scene out of the park. The way she’s transfixed on The Kid with tears welling in her eyes. The way her jaw drops slightly when The Kid sings, “If we got married, would that be cool?” The way it’s written all over her face by the end of the song how overwhelmed she is by his emotion and vulnerability. This dude isn’t like the others she’s messed around with and she looks like she knows this man has incredibly strong feelings about her and she’s kind of terrified about it. Respect to Apollonia. For those four minutes, she brought it without saying a word. In a movie full of amazing musical performances, “The Beautiful Ones” is my favorite.
I wish I could convey to you why “The Beautiful Ones” is the best work of art Prince created over the course of a 57-year life that produced so much brilliance. That probably makes me a shitty writer. It might also explain why Prince was Prince and the rest of us are mere mortals here still trying to wrap our heads around what he gave us ten years after he left. “The Beautiful Ones” is the best because every time I hear those drums that open the song – I mean every time – my eyes widen and I gasp. Buckle the fuck up. This isn’t just any other song. It’s “The Beautiful Ones”. No fancy tricks. A keyboard-heavy ballad in 4/4 time. A vocal performance that simmers for three minutes, then skips the boiling part and just explodes. For good measure, a sneaky good guitar solo is hiding behind that vocal explosion, too…and then it just…stops. You’re left breathless. You don’t just listen to it. You bask in it. I’m not worthy of it, yet somehow here I am. A self-proclaimed writer at a loss for words. How do you write about something so overwhelming? The best way for me to summarize is to simply state that in a Prince catalog filled with countless brilliant performances, “The Beautiful Ones” is my #1.
Then I read Questlove’s blurb on “The Beautiful Ones” and had my world turned upside down. Is it possible that “The Beautiful Ones” is not written about Apollonia or any woman, but about his mother?!? I’m not prepared to wrap my head around that at 1:15 AM on a Sunday. My tank is on E and Questlove is out here dropping bombs. Let me deal with this in my own time and I’ll come back with thoughts another day.
So that’s it. Now that I’m done, here’s what I learned. For starters, the knowledge gap between a virtuosic musician and living music encyclopedia like Questlove and an IT guy/admirer like is wide…but maybe not as wide as I thought. Questlove lives this stuff. I’m a goof. Still, by my count 49 of my choices were on his list, which I’ll take. I feel vindicated knowing that. Especially considering that I wasn’t aware he was going to count music from Prince’s side projects. You bet your ass songs like “777-9311”, “Nasty Girl”, and “The Screams of Passion” would’ve been high on my list if I had the same rule.
Questlove’s highest ranking song that could’ve been on my list was “Do Me, Baby” which he had all the way at #2. He also had “Sister” in his top ten. Both amazing songs, but I find both of them…flawed? I mean, “Sister” makes even me cringe for its entirety, which is only about 90 seconds. Meanwhile, “Do Me, Baby” contains one of my top pet peeves: When people add the sounds of simulated (or real) sex to a song. I don’t need to hear Prince and some random girl simultaneously climaxing. It doesn’t enhance my enjoyment of a song. In fact, it takes away from what I wrote about “Raspberry Beret” and “Little Red Corvette” above. I know Prince is having sex with the women he’s singing about. He can skip the reenactment.
Questlove’s column gave me a list of songs to revisit. Like a DVD commentary that explains the movie to you and makes you see it in a different light, Questlove’s short blurbs give me an opportunity to re-hear these songs and understand why someone like Questlove would put them in his top 100. On the flip side, I’ve always felt that Questo doesn’t give enough love to Prince’s late career. I’m sure he has his reasons, and he sort of explained it in the post. I’ll be the first to say Prince wasn’t exploring much new musical ground by the time the 21st century arrived, but there was still a lot worth listening to that was absent from his list.
You may recall way back almost a month ago I predicted that Questlove’s #1 song wouldn’t even be on my list. I’m glad and relieved to say I was dead wrong. The song made his list at #66. It’s called “It’s Gonna Be a Beautiful Night” from Sign O’ the Times, and for some reason I thought I heard Questlove – on multiple occasions – state that it was his favorite Prince song. Feels like it was on a podcast. No way I can find it and it probably never happened. For some reason for years I’ve been wondering why and how that was Questlove’s favorite Prince song.
Click the button above if you want to check out my Top 100 playlist on Apple Music. I had a lot of fun making this list. The key was not second guessing myself. If I kept rearranging songs I’d still be writing and probably only be somewhere in the 80s or 90s. I went with my gut, threw the list together hastily, and vowed not to rearrange once I did. I’m pleasantly surprised how satisfied I am with the results. I stand by it.
Since this post took me three weeks I’m late to the 10-year anniversary of Prince’s passing bandwagon, but better late than never. Thanks to Questlove for creating his list and giving me something to write about. Thanks to Prince for being Prince. We love you. Rest in peace.
mookiefantana 