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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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“You Got Lucky” (1982)

A video so cool it even impressed Michael Jackson, this Long After Dark standout was conceived by Petty and the Heartbreakers after falling under the sway of Mad Max. The lo-fi, post-apocalyptic clip stars the band as they park their Sleeper-style hover-car out in the middle of the desert, stumbling upon some ancient recording equipment and instruments. “You Got Lucky” was the perfect combination of clever and cheeky for an MTV era when artists were giddily throwing ideas against the wall to see what stuck. “That was when we really saw MTV change our daily lives,” Petty would say a couple decades later. “Not only were teenagers spotting me on the street, older people would spot me, too. We knew it was big.”

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“Don’t Come Around Here No More” (1985)

The only Petty clip to be nominated for Video of the Year – losing to Don Henley’s “The Boys of Summer” – “Don’t Come Around Here No More” found a visual complement to the song’s trippy, quietly unsettling vibe. Shot over a weekend at SIR Studios in Hollywood, the Jeff Stein-directed video re-creates the nightmare world of Alice in Wonderland, casting Petty as a slyly menacing Mad Hatter, complete with the singer’s trademark sunglasses, as he torments a terrified Alice. “I was knocked out when I saw the final cut,” Petty later said in I Want My MTV. “I played it 30 times in a row.” 

An up-and-coming actress, Louise Foley, got the part after a series of auditions. “They were looking for a sexy Alice,” she said in 2013, “so my mom and I went shopping and found a tight pink puff sleeve T-shirt, skintight black jeans … and a pair of kitten heel Mary Janes.” And although Petty in the video makes her life a living hell, eventually serving her up as cake to the rest of his costumed band members, Foley recalled that he couldn’t have been nicer. “Petty was a southern gentleman,” she said. “He was very soft-spoken and seemed very shy. I was confused by his demeanor because, at the time, rock stars were out-of-control, narcissistic, decadent egomaniacs. Petty didn’t have any of these traits.” She went on to date Heartbreakers drummer Stan Lynch for the next five years.

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“End of the Line” (1989)

When rock legends Bob Dylan, George Harrison and Roy Orbison teamed up with Tom Petty and ELO leader Jeff Lynne for the fun-loving Traveling Wilburys project, Petty was the little brother in the fictional family they created to give the side project its own mythology. And he loved every minute of it. “It was all great,” he said later, adding, “You’re in the best band you’ve seen, with all your heroes who are also your friends. It’s still hard to conceive, just a fabulous thing.” The wistful “End of the Line,” a feel-good salute to taking stock of one’s life, captured the easy camaraderie between the band members, and while the video is hardly groundbreaking, it magnifies the warmth and brotherhood that made the Wilburys such an unlikely, deeply rewarding endeavor. Petty gets the song’s signature line – “I’m just glad to be here / happy to be alive” – and the empty rocking chair in honor of Orbison, who died before the video, is a poignant reminder to appreciate what you have while it’s here. With Petty’s death, only two of the Wilburys remain. 

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“Runnin’ Down a Dream” (1989)

In 1905, comic-strip artist Winsor McCay unveiled Little Nemo in Slumberland, an adventure comic in which young Nemo (allegedly based on McCay’s son) goes on nocturnal journeys. Eighty-four years later, Petty swiped the idea for this Full Moon Fever clip, as an animated Tom and his cigar-chompin’ pal embark on a series of surreal quests involving killer clowns, gigantic rabbits and Native Americans. A live-action Petty provides the cheeky bookends to the video, dressed as the coolest dad-rock Saturday morning kids’ host of all time. 

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“Free Fallin'” (1989)

Petty put aside the high-concept angles for “Free Fallin’,” an appropriate move for a song whose gentle melody and wistful sentiment didn’t need a lot of fancy adornments. The songwriter was inspired to write the folk-ish hit by noting the scene to and from the recording studio: “I tried to grab a little bit of these characters on the road and it was kind of how I saw it,” he said. “It’s pretty true of that time and that era … The skateboarders and the shoppers and the young kids in the trendiest possible clothes and the auto-tellers and the drive-thru banks.” The video, filmed partly at the Westside Pavilion mall in Los Angeles, brings those images to life. Petty plays a sort of omniscient observer gliding above Southern California chronicling the song’s unnamed young woman (played by Devon Kidd) as she looks for love and contentment, finally finding some sense of serenity while skateboarding in slow-motion. Lots of Petty’s videos are funny, but “Free Fallin'” might be his most touching. 

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“Learning to Fly” (1991)

Into the Great Wide Open was written while Petty turned 40, which put him in an introspective mood. “I suppose I’m just working a lot of things out,” he said. “It’s very hard living your life as we have in tour buses and airplanes for all of this time. I think when I turned 40 I kind of did, as most people do, get a little reflective about ‘Where have we been? And where are we going?'” “Learning to Fly” is about the importance of constantly trying new things and learning from one’s mistakes, and the video frames that sentiment in luscious, melancholy black-and-white images, presenting us with a coming-of-age story that’s utterly surreal. The video’s young hero gets propositioned by an older woman, sees UFOs, and falls in love while surviving a fiery car crash. In the bizarre world of a Tom Petty video, that’s just a normal adolescent tale.

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“Into the Great Wide Open” (1991)

The title track to Tom Petty’s 1991 reunion with the Heartbreakers introduces us to Eddie, an aspiring musician who hits it big with his debut album, only to watch everything fall apart when he can’t deliver the follow-up. In the video, Petty plays our wise narrator (and cameos as Eddie’s roadie Bart) while Johnny Depp portrays poor, luckless Eddie. Extending the song’s instrumental passages in order to accommodate the video’s lengthy rise-then-fall narrative, “Into the Great Wide Open” featured cameos from Faye Dunaway and a pre-Friends Matt LeBlanc. But the video belongs to Depp, who was at his beatific best as the young hotshot who gets chewed up and spit out by the L.A. celebrity machine. This was long before the Pirates of the Caribbean superstardom when he was still one of Hollywood’s most beloved bad boys. The song was always meant to be a cautionary tale about fame – with modern eyes, we can see it now applies to Depp just as much as it does Eddie.

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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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