17. Tom Petty and the Heartbreakers “Mary Jane's Last Dance” (1993)

Album: Greatest Hits
Label: MCA
Producer: Rick Rubin

After his work with the Red Hot Chili Peppers, Rick Rubin turned his attention to a new partnership with an established rock icon, Tom Petty. Their work together throughout 1993 and 1994 at Ocean Way Studios in Los Angeles would yield a great album, Wildflowers.

Petty was the furthest Rick had travelled inland from his roots at the edges of musical propriety. The Peppers, at least, had been a crazy punk party band before their journey into the mainstream. Petty was middle America personified. But with one listen to the opening boom-bap of “You Don't Know How It Feels,” you understood that Rick was simply bringing his Beasties-meet-John-Bonham sensibilities to bear on a new canvas.

Curiously, the greatest production out of that initial collaboration did not end up on Petty's album, but rather his greatest hits compilation. Appropriate: “Mary Jane's Last Dance” was a great song; but Rick coaxed it into the realm of the American classic by evoking equal parts of Beatles and CSNY.

Says DJ Brainchild, co-host of Gordon Gartrell Radio and Questlove's partner-in-crime: “I'm slightly biased because the song takes place in my home state of Indiana, but it's easily one of Tom's best cuts of the '90s and also one of my favorite Rubin-produced tracks. The opening guitar riff is unforgettable, the hook is irresistible, and the video is fantastically creepy.”