Tom Petty’s career began in earnest in November 1976; that’s when he and his Heartbreakers released their self-titled debut album. That means the man spent just over 40 years as a rock star. That is a long, long time, and yet somehow the number seems too small. Petty feels like he’s been around a lot longer than 40 years. He feels like he’s always been with us — a calm and steady presence, an endless source of car-radio bangers. Petty was making classic-rock anthems pretty much until the final moment when classic-rock anthems could be made. He worked with his heroes and made them better. For millions of people out there, he’s what was playing when they drank their first beer, smoked their first joint, kissed their first kiss. He was a staple, a guy who would always be there. And now he’s gone.

Petty wasn’t the sort of rock star who demanded attention, whose antics became legendary. He was content to sit back and let other people bring the pyrotechnics. But in his long career, Petty, a legendarily good dude, still left us with magical moments that went beyond his many, many immortal songs. So in tribute to the Gainesville Angel, here are 20 memorable moments from the man’s long and storied career.

1. THE STEVIE NICKS DUETS

When Petty met Stevie Nicks, it was 1978. He was still an ascendant star, only one album in, while Nicks was the singer for quite possibly the biggest band on the face of the earth. But they made sense together. Their first duet was “Insider,” which showed up on Petty And The Heartbreakers’ 1978 album Hard Promises.

But the biggest and best of their songs together was “Stop Draggin’ My Heart Around,” a monster hit for Nicks in 1981. (It made it to #3, higher than any of the songs that Petty would record without Nicks.) On that song — and on all their songs together, really — those two voices meshed beautifully. Nicks had that sharp, lived-in intensity, and Petty’s laid-back drawl complemented it perfectly, giving it even more shape and dimension that it had on its own.

They worked again on Nicks’ “I Will Run To You” in 1983. They covered Jackie DeShannon’s glorious oldie “Needles And Pins” together in 1985. They toured together a couple of times, and they stayed great friends throughout the decades. Nicks has gone on record saying that she got the idea for “Edge Of Seventeen” from a conversation with Petty’s first wife Jane. (Jane had said that she met Petty at the “age of 17,” and thanks to that Florida accent, Nicks misheard her.) This past summer in London, Nicks showed up onstage with Petty as a surprise guest, and they sang “Stop Draggin’ My Heart Around” together one last time. And I love this story that Nicks tells about Petty:

Stevie Nicks in Rolling Stone, 2010, on why she loved him pic.twitter.com/W27qPKbv1V

— rob sheffield (@robsheff) October 2, 2017

2. THE TRAVELING WILBURYS

Petty was 37 — a year younger than I am now — when he joined the Traveling Wilburys, the all-legends supergroup that also featured George Harrison, Bob Dylan, Roy Orbison, and Jeff Lynne, all working under pseudonyms. Petty’s involvement with the group wasn’t by some grand design; he’d simply gone back to Harrison’s house to pick up a guitar that he’d left there when the band was having its first practice. But Petty’s inclusion in the group is still about as grand a validation as anyone could ever ask. Petty was the youngest member of the group, but by 1988, he had absolutely done enough to warrant inclusion. And while the band never quite did anything that equalled the talents of everyone involved — it’s honestly hard to imagine what would’ve done that — “Handle With Care” still goes.

3. THE KING OF THE HILL GUEST VOICE

Petty was probably too famous to play a recurring voice role on King Of The Hill, Mike Judge’s long-running animated sitcom, but he still showed up on 28 episodes over five years. Petty played Lucky, a no-account redneck living off of the settlement he got from slipping in a puddle of piss outside Costco. Lucky, who looked a lot like Petty, ended up dating and eventually marrying Hank Hill’s daughter Luanne. And he also played in the band Big Mountain Fudgecake — not as the singer, perversely enough.

4. THE “DON’T COME AROUND HERE NO MORE” VIDEO

Petty put a lot of work and care and craft and ingenuity into his music videos, a rare thing for a rock star of his vintage. (Most of his peers either didn’t quite get music videos, or they never brought themselves to embrace them.) And if you were a kid who turned on MTV at any time in the mid to late ’80s, there is a very good chance you got your brain scrambled by director Jeff Stein’s clip for “Don’t Come Around Here No More.” It’s a nightmare vision of Alice In Wonderland, with Petty playing the Mad Hatter and showing levels of gleeful malevolence that never made it into his music. The scene where Alice gets cut up into pieces of cake enraged parents’ groups and absolutely fucked me up when I was a kid.

5. THE “LAST NITE” RIFF

“Last Nite” was the Strokes’ biggest song and also arguably their best. And it famously stole its opening riff from Tom Petty’s “American Girl,” which might make Petty indirectly responsible for the entire early-’00s return-of-the-rock furor. And while it would’ve made sense for Petty to take the Strokes to court, he just sort of chuckled about it instead. “It didn’t bother me,” Petty told Rolling Stone in 2006, the same year that he took the Strokes on the road as openers.

6. THE AXL ROSE DUET

At the 1989 VMAs, Axl Rose and Izzy Stradlin, two of the main figures in the world’s biggest band, became temporary Heartbreakers. Rose, a vampire moving through the Valley, had a ragged chiffon wail that suited the “Free Fallin'” chorus perfectly, and it’s a surreal delight to see him doing his snake dance to that eternal campfire strum. The permanently bemused Petty seemed to think that Rose’s gesticulations were a little silly, but he seemed to be enjoying them, too. And then, as host Arsenio Hall wandered onstage, they launched into a “Heartbreak Hotel” cover together.

7. THE MOVIE STARS IN THE VIDEOS

In 1990, Johnny Depp played the leads in Edward Scissorhands and Cry-Baby. In 1991, his biggest role was Eddie, the would-be rock star in Julien Temple’s video for Petty’s “Into The Great Wide Open.” Depp really put everything into that video, too; it’s one of his most purely charismatic performances. (Also in that video: Faye Dunaway, Gabrielle Anwar, Terence Trent D’Arby, Matt LeBlanc.)

A couple of years later, Petty spent the video for “Mary Jane’s Last Dance,” one of his biggest hits, playing a creepy mortician who takes a beautiful woman’s dead body home. That body was Kim Basinger.

Movie stars on the level of Depp or Basinger didn’t show up in music videos very often. But who wouldn’t want to work with Tom Petty?

8. THE JONATHAN DEMME MOVIES WITH “AMERICAN GIRL” IN THEM

In The Silence Of The Lambs, Jonathan Demme’s 1991 Best Picture winner, we don’t get to spend much time with Catherine Martin, the senator’s daughter, before the serial killer Buffalo Bill abducts her. But we do get to see her driving alone at night and singing along with “American Girl,” and that’s enough to make us like her. Because who wouldn’t hear “American Girl” and just start singing?

Demme liked “American Girl” so much, in fact, that he brought it back in 2015’s Ricki And The Flash, the feature that he ended up making before he died earlier this year. During the opening credits of that movie, Meryl Streep’s fading rock star sings the song with her band. And that makes us like her, too.

9. THE BROKEN HAND STORY

In 1984, high and frustrated while trying to record Southern Accents, Petty punched a studio wall and broke his hand. He had to learn how to play guitar all over again. Petty was a born raconteur, and here he is, telling a 1985 LA audience all about it just before launching into “The Waiting.”

10. THE GEORGE HARRISON UKULELE STORY

Another example of Petty’s storytelling greatness: the moment in Martin Scorsese’s George Harrison documentary Living In The Material World where Petty talks about Harrison teaching him to play ukulele and then leaving a pile of ukuleles at his house. “He had a lot of ukuleles in the trunk.”

11. THE CONFEDERATE FLAG STORY

Three years before Tom Petty came out of Florida and released his debut album, Lynyrd Skynyrd came from Florida and released their debut album. That was Petty’s context. Unlike Skynyrd, Petty never really made the Confederate flag a part of his iconography. Like Skynyrd, though, Petty did play in front of one, at least for a little while. On his 1985 Southern Accents tour, that flag served as the backdrop. And two years ago, as the debate about that flag was raging, Petty told Rolling Stone about how he regretted that gesture, how he thought it was “a downright stupid thing to do”:

When we toured two years later, I noticed people in the audience wearing Confederate flag bandanas and things like that. One night, someone threw one onstage. I stopped everything and gave a speech about it. I said, “Look, this was to illustrate a character. This is not who we are. Having gone through this, I would prefer it if no one would ever bring a Confederate flag to our shows again because this isn’t who we are.”

It got a mixed reaction. There were some boos and some cheers. But honestly, it’s a little amazing to me because I never saw one again after that speech in that one town. Fortunately, that went away, but it left me feeling stupid. That’s the word I can use. I felt stupid. If I had just been a little more observant about things going on around me, it wouldn’t have happened. We did do a live record [Pack Up The Plantation: Live!] and there was a picture inside of us playing in front of one. I went back and had it removed from the record. It took a little time to get done, but it did get done. I still feel bad about it. I’ve just always regretted it. I would never do anything to hurt someone…

Again, people just need to think about how it looks to a black person. It’s just awful. It’s like how a swastika looks to a Jewish person. It just shouldn’t be on flagpoles.

Beyond the flag issue, we’re living in a time that I never thought we’d see. The way we’re losing black men and citizens in general is horrific. What’s going on in society is unforgivable. As a country, we should be more concerned with why the police are getting away with targeting black men and killing them for no reason. That’s a bigger issue than the flag. Years from now, people will look back on today and say, “You mean we privatized the prisons so there’s no profit unless the prison is full?” You’d think someone in kindergarten could figure out how stupid that is. We’re creating so many of our own problems.

Imagine if Skynyrd had ever come to that conclusion.

12. THE “HELLO CD LISTENERS” SKIT:

The first CD I ever heard was Petty’s Full Moon Fever. I checked it out of the Baltimore Public Library after my parents brought a CD player home. Right in the middle of the album, the music stops, and, with farm-animal noises in the background, we hear Petty saying, “Hello, CD listeners. We’ve come to the point in this album where those listening on cassette or records will have to stand up or sit down and turn over the record or tape. In fairness to those listeners, we’ll now take a few seconds before we begin side two. Thank you. Here’s side two.” Other than maybe the animal noises, this seemed perfectly reasonable to me at the time. I thought it was a little weird when I listened to another CD and it didn’t have a moment like that in the middle.

Fun fact: That skit is still there on the streaming version of Full Moon Fever.

13. THE SNL PERFORMANCE WITH DAVE GROHL:

In November 1994, Petty and the Heartbreakers were booked as musical guests on Saturday Night Live, but drummer Stan Lynch had just left the band. This was seven months after Kurt Cobain had killed himself, and former Nirvana drummer Dave Grohl was at loose ends. Someone from Petty’s management called and asked if he’d want to play drums for the Heartbreakers on SNL, and Grohl later told MTV, “It was the first time that I’d really looked forward to playing the drums since Nirvana ended.”

It’s never been confirmed, but rock lore has it that Petty offered Grohl the full-time Heartbreaker position and that Grohl turned it down to start Foo Fighters instead.

14. THE BEATIFIC PERFORMANCE IN THE POSTMAN:

1997’s The Postman is a bad movie. It’s Kevin Costner directing himself in a three-hour epic about a wandering mailman who brings hope to postapocalyptic America. Almost everything about it sucks. One thing that doesn’t suck is Tom Petty, doing a rare aging-rock-star acting turn. There’s a part in the movie where Costner looks at Petty and says, “I know you. You’re famous.” Petty, grinning loopily and looking high as hell, responds, “I was once, sorta, kinda. Not anymore.” So maybe Petty was playing himself? I like the idea that Petty was playing himself.

15. THE GARRY SHANDLING FRIENDSHIP:

In 1987 and 1988, Petty guested a bunch of times on It’s Garry Shandling’s Show, the comic-TV genius Shandling’s self-aware, deconstructed sitcom. Petty also put in a guest appearance on Shandling’s groundbreaking HBO series The Larry Sanders Show, doing a bit where he almost got into a fistfight with fellow late-night guest Greg Kinnear. Petty and Shandling remained good friends over the years, but for some reason, the only video I can find of the two of them online is this clip of Petty and Shandling, near what would turn out to be the end of their lives, bumming around Petty’s house together and cracking each other up for 20 minutes.

16. THE SIMPSONS LYRIC WORKSHOP:

“She prays that our schools don’t run out of chalk.” It’s so dumb, and it’s so funny, and I still laugh every time.

17. THE “FREE FALLIN'” SAMPLES:

Tom Petty wasn’t one of those rockers who shows up in sampled form on a whole lot of rap songs, but “Free Fallin’,” his most famous song, did make it in there a couple of times. And when it did, it sounded amazing. Case in point: “Fallin’,” De La Soul and Teenage Fanclub’s gorgeously sunny amble, the best song from 1993’s transcendently gimmicky Judgment Night soundtrack. Petty’s voice is just a distant echo on that song, but it still adds a whole lot.

Another example: “I’m Free,” a 2006 track that UGK legend Pimp C recorded shortly after finishing up a years-long prison sentence. As it turns out, Petty’s acoustic groove fits perfectly into Pimp’s country-rap template, and his voice helps capture that holy-fuck-I’m-out-of-jail elation.

18. THE CARL PERKINS DUET:

As a kid, Petty had his brain reshaped by Elvis Presley records. Later in life, he did what he could to pay tribute to the giants of ’50s rock ‘n’ roll; he was, after all, in a band with Roy Orbison. And on Go Cat Go!, the 1996 tribute album dedicated to the rockabilly originator Carl Perkins, Petty and his Heartbreakers teamed up with Perkins himself for a new version of “One More Shot” and proved that they would’ve done just fine as a rockabilly-revival band if that’s all they’d wanted to do.

19. THE GRACE JONES “BREAKDOWN” COVER:

Petty became a star in England before he broke through in America, and part of the reason was that he was marketed as a skinny-tie new waver, which is pretty hilarious when you consider the down-the-middle heartland rock star that he would become. Still, there was at least a bit of proto-new wave on Petty and the Heartbreakers’ self-titled 1976 debut; I always thought that “Breakdown” sounded a bit like the Police a year before the Police even existed.

In 1980, Grace Jones, probably the coolest person in the world at that time, went to Jamaica to record Warm Leatherette, an album of covers that she made with the legendary reggae production duo Sly & Robbie. With Sly & Robbie, Jones found a fascinating mutant sound that drew from reggae, disco, and new wave. And one of the sounds she adapted was “Breakdown.” She drew its mutant qualities all the way out, but it still sounded like “Breakdown.”

20. THE BATTLES WITH MCA:

In the late ’70s, Petty was recording for Shelter Records when the bigger MCA bought the label and, with it, Petty’s contract. Petty was not into the idea of being a pawn of record-business forces, and he refused to record for MCA. Petty wouldn’t let the label release his next album, and he paid the hundreds of thousands that it cost to record it out of his own pocket. He also declared bankruptcy in an effort to get out of his contract. It worked. MCA agreed to release Petty from his contract, and then they signed him to a new contract, for $3 million.

The first album that Petty ended up releasing on MCA was 1979’s Damn The Torpedoes, which turned Petty into a huge star. After that album blew up, MCA wanted to charge more for Petty’s next album, 1981’s Hard Promises. Apparently, it was industry standard at the time to sell superstars’ albums for $9.98 while charging $8.98 for everyone else’s records. ($9.98 in 1981 dollars translates to $28.16 today. Records were expensive!) Petty wasn’t having it. And he threatened to change the album’s title to $8.98 unless the label would agree to charge the regular amount for it.

So that’s Tom Petty: A guy willing to go to war with his label, on behalf of his fans, for a dollar, and for principle. We were lucky to have him.