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The 10 Greatest Tom Petty Music Videos

From “Don’t Come Around Here No More” to “Free Fallin'” – the lead Heartbreaker’s best, funniest, most far-out videos

Thinking of the musicians who became superstars thanks to MTV, names like Michael Jackson, George Michael, Madonna and Prince come to mind. But perhaps the most underrated major videomaker of the era was a young man from Gainesville, Florida who perfected an indelible mix of Byrds-ian melody and Stones-like punch on albums like Damn the Torpedoes and Full Moon Fever. 

Tom Petty, who died October 2nd at the age of 66, was not your typical MTV figurehead. He didn’t dance, he didn’t have movie-star looks and, most importantly, he couldn’t stand music videos. “I didn’t much like making videos – the hours were insane,” he admitted in I Want My MTV: The Uncensored Story of the Music Video Revolution. “But I liked the outcome. My band hated making videos. They didn’t want to go anywhere near them. I didn’t blame them. But I didn’t have a choice. I had to be in them.”

No matter their misgivings, Tom Petty and the Heartbreakers were one of the best video bands of the Eighties and Nineties – the singer would end up winning three Moonmen while delivering innovative, funny clips for radio-ready rock songs. And credit him this: He resisted the popular trend to just feature hot babes in his videos. “I knew it would cheapen our long-term play,” Petty said. “I wasn’t happy the way videos started to exploit women. I thought, we’re all better than this.”

Here’s a look back at 10 of his most memorable videos. Along the way, you’ll see how an initially resistant Petty learned how to shape an onscreen persona – that of a friendly, impish prankster – which would become his MTV avatar. He may not have liked making music videos, but he left us with some classics.

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“Mary Jane’s Last Dance” (1993)

A few years before winning an Oscar for L.A. Confidential, Kim Basinger delivered one of her other great performances in the role of a beautiful corpse who bewitches a lowly mortician’s assistant (played by Petty). “Now that was one of the coolest things I’ve ever done in my life,” she later said. “It was classic, wasn’t it? He was a doll, and he was so sweet and asked me to do it, and both of us are extremely shy so we just said three words to each other the whole time.” “Mary Jane’s Last Dance,” which won Petty the second of his three MTV Video Music Awards (for Best Male Video), is among Petty’s most intricate story videos, as the assistant brings Basinger home, trying to make a life with her before finally giving up and discarding her into the sea. Petty’s rationale for casting Basinger was simple: “I said, ‘She’s got to look really good, or why would he keep her around after she’s dead?'” 

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“You Don’t Know How It Feels” (1994)

At a time when videos were becoming more and more elaborate, Petty and director Phil Joanou came up with an idea that was deceptively straightforward: one continuous shot of Petty performing this Grammy-winning highlight from Wildflowers with deadpan sincerity while all types of oddness rotates around in the background. In the process, the “You Don’t Know How It Feels” video perfectly encapsulated the song’s stoned, laidback sense of disillusionment and quiet defiance. Bonnie and Clyde knock off a bank, a wrecking ball smashes through a wall, a background extra suddenly takes the mic away from Petty – but no matter what happens, Tom remains, as always, one cool customer.

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