Welcome back for our final week of the Amy Winehouse Mix CD. Today is the 20th track on the mixtape. It’s the sixth track from Amy’s legendary sophomore album Back To Black. Written by Amy Winehouse and produced by Mark Ronson. It was also the fifth and final single from Back To Black. It topped out at #46 on the UK Singles Chart because apparently people are either deaf, have no taste, are complete fucking idiots, or likely some combination of all of those things. Someone with an understanding of good music was paying attention because “Love Is A Losing Game” earned Amy yet another Ivor Novello Award for Best Song Musically and Lyrically.
As I’ve said in past posts, the heart of Back To Black is tracks 5-8. Track 5 is “Back To Black”. The epic. The devastation. The immediate moments after heartbreak. Track 7 is “Tears Dry On Their Own”. The acceptance. More upbeat. Moving On. Track 6 is “Love Is A Losing Game”. The in-between. 2:35 of pure melancholy. Amy at her lowest.
For you I was a flame
Love is a losing game
Five-story fire as you came
Love is a losing game
One I wish I never played
Oh, what a mess we made
And now the final frame
Love is a losing game
Those are the words of a person who’s been completely shattered. It takes courage for someone to put any kind of art out into the world. For Amy to create something like this that captures her feelings when she was at her lowest is unbelievable to me. While so many others attempt to hide any vulnerabilities she seems to revel in showcasing them. Instead of getting just another talented vocalist putting out a pop album that’ll sell a few records and make some money for a record label Amy gave us a timeless piece of art that catapulted her to legendary status. That’s not just me talking. Apple Music recently ranked Back To Black the #8 album of all time. My only complaint is that wasn’t high enough.
Prince also took notice. In August and September of 2007 Prince played 21 sold out shows at O2 Arena in London. On September 21, 2007 – the final night of his residency – Prince brought Amy onstage at the aftershow. The song: “Love Is A Losing Game”. It’s a one-of-a-kind arrangement of the song. The NPG playing a slow soul/gospel version of the song heavy on guitar and organs. Amy on vocals. Prince on electric guitar. If you click the YouTube video above to listen to it – and you should – realize it’s nearly five minutes before you hear Amy’s voice. I wish I could find a decent video of this performance. They all look terrible. I’m sure the Prince Estate has one somewhere. Please let us see it!
You’d think Amy and Prince performing that song together would automatically make it my favorite live version, but it’s not. For that we go back – one more time – to her set on MTV 45th at Night and another one-of-a-kind performance. This time with one of my favorite rappers, Yasiin Bey a.k.a. Mos Def (Thanks to my autocorrect for continually attempting to change Mos Def to Mrs Def, which made me laugh out loud the first time I saw it). There are so many things about this performance that stand out. First, Amy completely misses her cue and has to stop the song and start over. Apparently this happened numerous times that night, but this is the one MTV left in the televised version of the show. You get to see her humor as she apologizes saying, “There’s so much better things to be doing than watch me fuck up.” When the song does officially start the Dap Kings are perfect, once again, and Amy sounds fantastic. The highlight for me comes when Mos Def drops a verse. There isn’t another rapper that I’d choose to add a verse to an Amy Winehouse track. While Mos is does his thing Amy starts improvising. I’m pretty sure she’s just messing around, but it’s angelic. Not ashamed to say that this version of “Love Is A Losing Game” has actually moved me to tears. Beautiful music.
It took 20 tracks to get here, but we’ve reached the emotional low point with “Love Is A Losing Game”. There’s nowhere to go but up now. Tomorrow we recover with the song that I consider to be Amy’s finest songwriting, and that’s saying a lot. We’ll get into it tomorrow. Enjoy your Monday.
mookiefantana 