De La Playlist

I’ve written many times here about how difficult it was to be a fan of hip hop growing up in Green Bay pre-internet, especially if you didn’t have regular access to MTV. Your best option was to buy tapes based on the cover art and hope for the best. One day I discovered a cassette at Fox River Mall called Monster TV Rap Hits. Songs from 17 different rappers for the cost of one cassette tape! On the drive home I sat in the backseat of our car with my walkman, pressed play, and heard De La Soul for the first time. “Me Myself and I” was the first song on the tape. I also remember pressing rewind as soon as it was over and playing it again…and again…

My memory of what happened after that was foggy. I know somehow I got my hands on De La’s debut album 3 Feet High and Rising not long after that. I got De La Soul is Dead for my 15th birthday. I didn’t have much insight into the art of sampling at the time. I just knew they were creating sounds unlike anyone I’d heard up until that point. They created alternative hip hop, or at least were the first to deliver it to a wide audience. Adding to the mystique was their vibe. Amazing rappers who seemed kinda nerdy. They had silly names and half the tracks on their first two albums were ridiculous skits about how wack they were or nonsense like “De La Orgee” or “A Little Bit of Soap”.

De La made it cool to be left of center. If their music was corny or they couldn’t rap it wouldn’t have worked. Instead, Pos and Dave had skills and lyrics to compete with the greats and Maseo and Prince Paul were sampling better than anyone in the business. The music couldn’t have been better. I’ve recently seen lists comparing their first four-album run to Stevie Wonder’s streak of amazing albums in the 70s. That’s how good De La Soul was.

So why all the hype now? Because they’ve been in a battle for years over ownership of their music, sample clearing, and streaming rights. That’s probably not 100% accurate, but that’s the 30,000 foot view, anyway. After years of waiting for their music to hit streaming services it finally happened last week. An entire generation of music listeners hasn’t been able to listen unless you’ve been able to find their CDs at a resale store or buy them on eBay.

I had all of De La’s CDs. When I got my first iPod back in the 2000s I imported all of my CDs into iTunes. Once that was done I figured I didn’t need hundreds of CDs anymore so I sold most of them on eBay. Then, about five years ago in a world class brain fart that haunts me to this day, I accidentally deleted all of my music when I was making a road trip playlist. How does one do that, you might be asking? I wanted to delete some of the dead weight out of my library and I thought I selected a few albums to delete, but I somehow selected all of them. The entire fucking library. When I hit the delete button I thought, “Why is this taking so long to delete three albums?” To my horror I realized what I had done and hammered on the cancel button, but apparently it was too late. My Apple Music library full of rarities and curated playlists was gone. I pay Apple $25/year for Apple Music in the Cloud, but I found out the hard way that it just means they store your music in the cloud. They don’t backup your music in the cloud. Subtle difference. Shit.

After months of work I was able to recreate most of what I had before. Most of it. No more De La Soul because their music wasn’t streaming. Through extensive crate digging and lucky timing I was able to acquire De La’s first three albums on vinyl. I’ve been able to listen to them on my turntable, but most of my music listening takes place through my phone while driving in my truck or sitting at my desk. I can’t take my De La records with me in my pocket. This has meant that every time I’ve wanted to hear a De La album for the past several years I’ve had to be at my turntable and it was obviously only the three albums I owned. Every playlist I have has been incomplete without De La’s classics.

Now we all have access to them again and it feels like a holiday. I want my kids to listen. I want their friends to listen. I hear what passes for hip hop in 2023 and I need them to know it wasn’t always this bleak. I want them to experience the same feeling I had when I heard “Potholes in my Lawn” and “A Rollerskating Jam Named Saturdays” for the first time.” So, I’ve prepared my De La Playlist. I have over three decades of De La fandom behind me. These are my favorite De La tracks and the music I’d recommend to anyone unfamiliar with them. Only one rule: I’m sticking to the first four albums. They’re the four I’ve been listening to for three decades. Not to say that there aren’t great tracks on their later albums, but I’m going with strictly classics on this playlist.

If you’re an Apple Music subscriber and you just want to hear the playlist without reading my bullshit click here.

Me Myself and I

I’ll start with the obligatory hit. This was De La’s highest charting song and the one that people recognize most. It’s a perfect hip hop song for radio. Posdnuos and Dave rapping about individuality over a Funkadelic sample. Clever, funny, fun, and funky as hell. Still hits 34 years later.

The Magic Number

Someone must’ve decided this was the perfect track to reintroduce De La to the masses because most of the advertising I’ve seen in the past two months has contained this track. Everything I said about “Me Myself and I” applies here, but the sampling and lyrics are next level. Prince Paul chopped up pieces of at least nine different tracks to build this song, but the most recognizable pieces are taken from the Schoolhouse Rock song “Three is a Magic Number”. Who takes a Schoolhouse Rock song and transforms it into something funky as hell? De La, that’s who. Add mind-bending lyrics (see the YouTube lyric video above) and you have the first song you hear when you drop the needle (or press play) on De La’s debut 1989 album 3 Feet High and Rising. Another masterpiece.

Eye Know

Anyone in my family can tell you that I’m not a fan of Steely Dan. Seems like they’d (he’d?…is Steely Dan just a guy named Dan?) be right up my alley but something about certain music from that era makes my skin crawl. Yet the sample of Steely Dan’s “Peg” combined with Otis Redding’s whistling lays the foundation for this mellow track. It’s a hip hop song that handles the topic of love in a way not often heard before or since. Pos, Trugoy, and Maseo were barely 20 years old but they were already light years ahead of their peers topically and lyrically. It’s introspective, soulful, and somehow not even remotely corny. Just a beautiful piece of art.

Transmitting Live From Mars

Fans of De La might be scratching their heads at the inclusion of this track on my playlist. I wanted something here to represent the unexplainable, weird music scattered throughout De La’s albums. When I was a kid this song legitimately creeped me out, but in a good way. An old song by a band called The Turtles slowed down to a crawl with random French and record scratching. It’s 72 seconds of complete nonsense and I’m here for all of it. 3 Feet High and Rising wouldn’t be the same without it. If you prefer other nonsense from this album instead, feel free to insert “Can U Keep a Secret”, “De La Orgee”, “Take it Off”, or “A Little Bit of Soap” in this spot. I just need something to represent the strange De La humor. Side note: When the record label’s lawyers scoured 3 Feet High and Rising for samples to make sure they cleared all of them before releasing the album they missed one. The Turtles sample from this track. The Turtles apparently sued Tommy Boy and made out with hundreds of thousands of dollars. This track was an expensive joke. Oops.

Say No Go

I’m a sucker for a good Hall & Oates track and they get no better than “I Can’t Go For That (No Can Do)”.

A Roller Skating Jam Named “Saturdays”

I’m not sure music gets better than this song. I heard someone ask the question recently, “What’s the one song that could put you in a good mood anytime you hear it?” Roller Skating Jam might be my answer. Who but De La could take samples from Chicago, Frankie Valli, and Chic (among others) and mash them up into something this amazing. This song might also remind me of high school as much as anything. It’s perfect.

Bitties in the BK Lounge

“Bitties” is one track, but it’s three different acts. Act I: Trugoy trying to use his celebrity to get better service from a lousy Burger King employee. Act II: Rude customers and a cashier at Burger King exchanging insults. Act III: I have no idea what’s going on here, but it’s a funky as hell Jimmy Spicer sample and I wish it lasted ten minutes longer.

Millie Pulled a Pistol on Santa

In case you hadn’t noticed, the past few tracks have been pulled from De La’ sophomore album De La Soul is Dead. After being promoted as hippies who loved daisies and day glo, they decided to kill that image and take their music in a different direction. De La Soul is Dead is flawless. Less silly than their debut album, but not so much that they lost their personality. Nowhere was that more evident than “Millie Pulled a Pistol on Santa”. De La’s own words, this song has “a title that sounds silly.” As it turns out, there’s nothing even remotely silly about this track. I’m not going to spoil it because I want you to press play and listen in shock at the truly troubling tale they tell. It’s brilliant songwriting and I promise you no matter what you think this song is about, you’re wrong.

Ring Ring Ring (Ha Ha Hey)

In my opinion De La Soul is Dead is De La’s best album. It’s in my top 5 hip hop albums. As much as I love everything happening on this album, “Ring Ring Ring” might be the best encapsulation of everything De La in one song. It has every element I want out of a De La Soul track. Ridiculously funky. Clever lyricism. A bit of humor. A few surprises. I always loved this song, but in the past few days since I’ve had these albums on repeat non-stop my first strong reaction is, “How the hell was ‘Ring Ring Ring’ not the De La song I’ve been listening to on repeat for the past 32 years?”

Keepin’ the Faith

Everything I said about “Ring Ring Ring” above, just to a slightly lesser degree. Another brilliant track and I slept on it all these years because it’s the 26th track on the album. Remember, I’ve been playing this exclusively on vinyl for the five-plus years. If this had been the second track I would’ve heard it more. A poor excuse for basically ignoring a song, but unfortunately it’s true in this case.

Patti Dooke

We’re on to De La’s third album, 1993’s Buhloone Mindstate. At this point De La seemed to already have had enough of the record industry. Case in point: “Patti Dooke”, a track about their discontent with white mainstream trying to control the direction of black music. “Patti Dooke” contains as many eclectic samples as its predecessors, but it feels less dusty. Jazz stalwarts Maceo Parker, Fred Wesley, and Pee Wee Ellis join De La on this track and give it a more polished vibe. The end result is still the same: brilliant lyricism, funk, and a clever message.

Ego Trippin’ (Part Two)

De La Soul was never about the usual trappings of hip hop. That’s what made them so unique. They never tried to be something they weren’t. After a few albums they became proficient at calling out rappers who were in it for what they considered to be the wrong reasons. Some tracks took a serious look at this topic (more on that later) but “Ego Trippin'” was a parody on the bragging that has always been pervasive in hip hop.


I’m gonna be completely honest here: I don’t know what this song is about. I also don’t care. Just Pos and Dave rapping over a funky ass beat and a dope Michael Jackson deep cut. This track is about the vibe. I don’t care what the message is.

I Am I Be

I’ll just come out and say it: This is De La Soul’s best song. I’m not saying it’s my favorite. I’m saying it’s the best. Maceo, Fred, and Pee Wee are back bringing their live jazz musicianship on this track, but it’s the brilliant lyrics that make this song what it is. Posdnuos opens the track with arguably the best verse in the De La discography up to that point…until Dave shows up and raises the bar with his verse. Here’s just a taste:

It’s just mind over matter and what matters is that 
The mind isn’t guided by the punished shade 
I keep the walking on the right side 
But I won’t judge the next who handles walking on the wrong 
‘Cause that’s how he wants to be, no difference, see 
I want to be like the name of this song, I am

For years Pos and Dave sounded so similar to me that I often couldn’t tell the difference. Then I made a point of trying to determine who was who when I listened to them. When I heard “I Am I Be” I decided that Dave got the slight edge in my internal head-to-head battle of who was the best MC in De La Soul simply based on his performance in this song. Then I heard something just last week that rocked me and made me question my ruling: Pos wrote Dave’s verse. Posdnuos wrote all of the lyrics in this song. Dave rapped Pos’s lyrics. Damn. Now I’m questioning everything. Ultimately, none of it matters because they’re both brilliant. It also feels like as good a time as any to say rest in peace to Dave. I really wish he was here for this comeback.

The Bizness

On to the fourth album, 1996’s Stakes is High. At this point De La Soul were elder statesmen. It’s ridiculous to imagine at this age, but at this point they were in their late-20s and four albums into their rap careers. They were getting up there. Rap was still a relatively new genre and there weren’t a bunch of old rappers doing the nostalgia circuit like they do now. De La realized that this album might be their last chance to use their massive spotlight to get their music out, and to a large degree that was true. Another claim De La Soul can make is that they used this album to help usher in the next generation of amazing MCs. A young rapper from Chicago shares the mic with De La on this track. Little did we know this guy would become a Grammy and Oscar winning household name.


If you wanted to complain about De La Soul, I guess you could say they spent too much time rapping about everything that was wrong with rap music. I would argue that most rappers spend their time rapping about stuff a lot less important than that, but I understand the argument. On “Dinninit” De La is making another song about the excesses of hip hop, but in this case disguising it as a party song. I just think it’s a dope track.

Big Brother Beat

This has low key been my favorite track from Stakes is High from the moment I heard it. As much as I love De La Soul, this is the song that introduced me to the mighty Mos Def. Pound for pound I think he’s the greatest MC to ever bless the mic, and on this track we get to hear him drop bars with two more of the greatest of all time. Like I said, this album De La clearly understood their role as elder statesmen and brought in a lot of great young talent.

Stakes is High

Like I said, De La loved to rap about the state of hip hop and – at least on this album – embraced the young talent. They employed a relatively unknown James Yancey – a.k.a. J. Dilla – to create the beat for this anthem. Dilla’s production adds an uneasiness to a track that already has its fair share of urgency. Stakes is high. De La was rapping for the soul of the art form they love on this track. They were tired of the direction hip hop was headed and didn’t pull punches:

I’m sick of bitches shakin’ asses
I’m sick of talkin’ ’bout blunts, sick of Versace glasses
Sick of slang, sick of half-ass awards shows
Sick of name-brand clothes
Sick of R&B bitches over bullshit tracks
Cocaine and crack, which brings sickness to blacks
Sick of swoll’-head rappers with they sickenin’ raps
Clappers of gats, makin’ the whole sick world collapse
The facts are gettin’ sicker, even sicker, perhaps
I Stickabush to make a bundle to escape this synapse

Coming from the wrong person this could feel like the rant of a Fox News primetime pundit. Coming from De La Soul it was a desperate plea to pull hip hop back from the mainstream, corporate record label, puffy suit, jiggy bullshit hell it was in.

Of course, not even greats like De La Soul could save it. I’m sure this is nostalgia talking. Every person thinks the music from their teens and twenties was the best. I’m no different. For my money, nothing I’ve heard from rappers in the past twenty years comes close to the skill, wit, and creativity displayed by De La Soul on this playlist. Maybe I need to let go of the battle they fought with “Stakes is High” 27 years ago. Regardless, I’ll circle back to what I said at the beginning: I want my kids’ generation to know hip hop didn’t always sound like the way it does now. I don’t want them wondering why dad loves hip hop so much when the only examples they’ve gotten are Drake, Moneybagg Yo, and Cardi B. That shit is depressing.

This playlist is just the tip of the iceberg. I recommend taking in their entire discography because it’s all worth your time including their later stuff that I ignored in this post. It’s finally all out there for anyone with a streaming subscription to play. I hope people are listening. Long live De La Soul. Rest in peace Dave Jolicoeur.

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