Phish and Jay-Z- “99 Problems”/”Big Pimpin” ytaudio(om2EQ7YXork)
Jay-Z’s surprise appearance at a 2004 Brooklyn Phish show probably jolted the jam-band crowd. Phish backs Hov up for “99 Problems,” with the song losing its hard-edged guitar pyrotechnics, and a devastating “Big Pimpin,” which sounds like the Grateful Dead colliding with Bed-Stuy.
Metallica and Lou Reed – “Sweet Jane” ytaudio(6hHOZpob4_c)
Somehow, James Hetfield was able to extract a smile out of Lou Reed before muscling through “Sweet Jane” at the Rock & Roll Hall of Fame’s 25th anniversary party this fall. It’s fun to listen to the time-signature complexities and epic heaviness of Metallica condensed down into a simple three chord song, even though Kirk Hammett somehow manages to tear through four guitar solos, undercutting Reed’s vulnerable warble.
Sonic Youth and Cypress Hill – “I Love You Mary Jane” ytaudio(xRkpOdRbbsc)
This rap-rock collaboration came off of the Judgment Night movie soundtrack, which also featured Slayer with Ice-T and Mudhoney with Sir Mix-A-Lot. The guitar squeals and shrieks of Sonic Youth would typically hurt a stoner’s brain, but here they chill things out with a mellow slow jam. You can hear Thurston Moore’s breathy background vocals against the nasal paeans to pot.
Elton John and Eminem – “Stan” ytaudio(ZY2p7oE7Bpw)
Remember when Eminem used to be controversial and culturally relevant? The vitriol against Eminem’s homophobic lyrics was at its height at the time of the 2001 Grammys, where he paired with Elton John for an inspired rendition of the suicidal stalker letter “Stan.” John’s jazzy piano inflections and baritone elevate this version above the scratchy album original, with Eminem finding the utter pain and desperation to infect his inimitable flow. Em still hasn’t regained this haunting anger that constituted his best work.
Iggy Pop and Peaches – “Kick It” ytaudio(ILjUe-znXE4)
A grating car alarm, fitting for a song culled from a racing video game, melds into Iggy and Peaches trading screechy battle lines over chunky freeway guitars. In the video, Iggy struts shirtless, and Peaches come close as well. The song functions as an Iggy biography, referencing numerous Stooges songs and Iggy’s late-career flight to Berlin. Iggy also covered the song “Rock Show” on his 2003 album Skull Ring, with Peaches returning the favor by covering “Search and Destroy” on the War Child charity album.
Kenny Rogers and Wyclef Jean – “The Gambler” ytaudio(bx7PUOvTFJk)
This one is just uncomfortable, but we had to include it.