Tom Petty holds up his award for the Michael Jackson Video Vanguard Award at the 1994 MTV Video Music Awards. (AP Photo/Bebeto Matthews)

Tom Petty, who died Monday at 66, wasn’t the most likely music video star. Skeletal and toothy with a hangdog look and a collection of top hats, he wasn’t the aspirational rock god, driving around in a sports car surrounded by voluptuous, barely dressed women.

But it didn’t matter. Even though he burst onto the MTV scene at a relatively late age, he still managed to connect with a younger generation of rabid video fans who readily consumed the wacky, inventive and occasionally controversial videos that Petty and his band produced. You can see why: The videos were funny and strange, packed with so many stunning details that you could watch them again and again without seeing everything. He rarely took the easy route of cobbling together concert footage.

He was “much more interested in storytelling than band performance videos,” said Keir McFarlane, the director of “Mary Jane’s Last Dance.” “His music videos were already mini movies with full-blown characters and complex story lines.”

Here’s a look back at nine of the most memorable, starting with a few of the most obvious before taking a detour into some deeper cuts.

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

The “Alice in Wonderland”-themed video marked the first time the band received a nomination for an MTV Video Music Award. The psychedelic spectacle was up for five, including video of the year, and won one, for best special effects.

The effects were certainly special — but also controversial. Starring Wish Foley as Alice, the video became a target for Tipper Gore and her Parents Music Resource Center, because of what they deemed disturbing images. The video culminates with Alice lying on a table, her body made of cake, while Petty’s Mad Hatter and the rest of his tea party slice her into tasty pieces.

“When people said that the cutting of the cake promoted cruelty to women, I had to laugh that people took it so damn seriously,” Foley said during an interview for the book “I Want My MTV,” by Rob Tannenbaum and Craig Marks.

Meanwhile, the video’s director, Jeff Stein, said he was attacked by a parent-teacher organization for supporting cannibalism. The MTV generation didn’t seem to mind.

“Mary Jane’s Last Dance” (1993)

If parents thought “Don’t Come Around Here No More” was disturbing, then we can only imagine how they felt about the video for “Mary Jane’s Last Dance,” which won best male video at the MTV Video Music Awards. It starred Kim Basinger as a beautiful corpse, while Petty played a morgue worker who dresses her up and borrows her for an evening of dinner and dancing followed by a resurrection ritual.

It may have been macabre, but it gave Petty the opportunity to flex some acting muscles, and he turned out to have a talent for dark comedy, especially in the scene when he props up his dead date and asks her if she wants to watch some television, only to have her tip over.

McFarlane, the director, was struck by how Petty portrayed the morgue attendant as someone truly in love; the video felt more profound and less creepy that way.

“That made all the difference to the soul of the story, and why perhaps people are still drawn to it,” he said. “In every scene, he really cared for the dead girl in a kind gentle way, finally releasing her to the ocean waves.”

“Into the Great Wide Open” (1991)

Basinger isn’t the only big star to show up in one of Petty’s videos. “Into the Great Wide Open” was an A-list heavy event, with Johnny Depp playing Eddie, the song’s “rebel without a clue,” plus Faye Dunaway as his manager and Gabrielle Anwar as his love interest.

In a wry twist, Petty plays himself as the storyteller — it was his circular glasses period — and also Eddie’s “roadie named Bart.”

Petty’s videos tended to be experimental, with plenty of special effects, and even though this one had a straightforward narrative structure, the interludes with the Heartbreakers show the band miniaturized, playing on the desk where Petty sits singing the story.

The video lost out on the best male video award that year, but was renominated in 2009 for the category of best video that should have won a Moonman. It lost — again — this time to “Sabotage” by the Beastie Boys.

“Yer So Bad” (1989)

Petty seemed to relish playing bizarre characters in his videos, but he was also great here as the droll, top hat-wearing narrator, sitting and watching the crazy personalities around him. The people don’t get much wackier than in “Yer So Bad,” which pretty forcefully conveyed the band’s disdain for yuppies.

Former “Saturday Night Live” cast member Charles Rocket (who famously dropped an f-bomb on live television) played a divorced businessman whose fancy convertible can’t quite compensate for his loneliness. His closest companion is a blow-up doll. Meanwhile, other incongruous images include men wearing fake pregnant bellies and a tribe doing some sort of ceremony inside of a half-built house in a future subdivision.

“You Don’t Know How It Feels” (1994)

This was Petty’s second Moonman for best male video. It’s one long take and features Petty in the foreground with a microphone, harmonica and guitar, spinning on a stage while blurry activity unfolds behind him, including a couple getting ready in a bedroom, jugglers at a circus and an armed robbery.

At one point, the focus leaves Petty to show two people having an affair inside of a bank, and then a woman approaches Petty, shooing him away so she can take over singing. Petty again nails the acting, delivering a solid double-take before disappearing from view.

“You Got Lucky” (1982)

The band got fairly experimental with this early video, which gave the guys their first taste of fame. It takes place in a dusty post-apocalyptic hellscape inspired by “Mad Max,” and the music starts when Petty presses play on a cassette player. In “I Want My MTV,” Petty reminisced that Michael Jackson called to say what a great idea that opening was.

After the video came out, Petty realized the difference music videos make. Suddenly people of all ages were approaching him on the street, recognizing him from MTV.

“Jammin’ Me” (1987)

“Jammin Me” was basically a list of grievances set to music, which Petty co-wrote with Bob Dylan. (Sample lyrics: “Take back your insurance/Baby nothings guaranteed/Take back your acid rain/Let your T.V. bleed.”)

The video, meanwhile, had the band set up in front of a green screen featuring a barrage of images — an atomic bomb exploding, military tanks and dogs getting their teeth brushed. The special effects look pretty rudimentary to our 2017 eyes but it would have looked pretty newfangled back in 1987, especially the part where Petty grabs handfuls of TV static while complaining about Vanessa Redgrave and Eddie Murphy, for some reason.

“Runnin’ Down a Dream” (1989)

The video for this 1989 hit starts a lot like “Into the Great Wide Open,” with Petty opening a book to reveal a story. This one, though, is animated with black and white images inspired by Winsor McCay’s comic strip “Little Nemo in Slumberland” from the early 1900s.

Petty is the cartoon star of the story, on another dreamy “Alice in Wonderland”-style journey that takes him to the moon and beyond.

“Walls (Circus)” (1996)

The video starts off with a striking image — a bright yellow cab pulling up to a drab, black-and-white backdrop — and the visuals only get more stunning from there. Taking place in a circus, it’s a colorful fantasia with purple elephants, fuchsia lotus flowers coming into bloom and snake charmers.

It all culminates with an image that’s particularly hard to shake today. Petty sings, “I can’t hold out forever/Even walls fall down” before collapsing on the ground. The colorful activity, meanwhile, continues to swirl around him.

This post has been updated.

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