Dan Snierson
October 03, 2017 AT 08:31 AM EDT

The day after after the massacre at a Las Vegas country music festival show that left at least 59 people dead, America was also mourning the loss of an essential icon of rock and Americana: Tom Petty died on Monday night at the age of 66. Petty, who was inducted into the Rock and Roll Hall of Fame in 2002, also showcased his wit in Hollywood on occasion, including in recurring guest roles on It’s Garry Shandling’s Show and King of the Hill, as well as in an episode of The Larry Sanders Show and an episode of The Simpsons titled “How I Spent My Strummer Vacation,” which is considered one of the show’s premier post-Golden age installments.

In the 2002 Simpsons episode — which sent Homer to rock & roll fantasy camp and also featured such celebrity instructors as Mick Jagger, Keith Richards, Elvis Costello, Lenny Kravitz, and Brian Setzer — Petty holds a frustrating lyric workshop around the campfire with Homer, Otto, Chief Wiggum, and others. “Lyrics are the hardest part of songwriting, but when you come up with something meaningful and heartfelt…,” Petty starts to explain to the group, only to be interrupted by Homer, who shouts “Boring!” and tells him, “Rock stars are supposed to be about drinking, and getting drunk and boozing it up!” After a frustrated Petty asks, “You just want mindless, generic rock?” and everyone answers in the affirmative, he groans, flips over his acoustic guitar, which turns out to be electric on the other side, and starts singing a song that is interrupted by the group’s approval and disapproval: “See that drunk girl speeding down the street” (Cheers) “She’s worried about public schools” (Boos) “She likes to party, she likes to rock “(Cheers) “She prays that our schools don’t run out of chalk” (Boos).

Simpsons producer Mike Scully, who wrote and produced the episode, has been a dedicated Petty fan who first saw him perform in the mid-’70s and attended the last stop of Petty’s 40th-anniversary tour on Sept. 25 at the Hollywood Bowl, which would prove to be his final gig. “I’m in shock,” Scully tells EW. “He was in great form, the band sounded fantastic and he was really funny… There was no glitz to the show. It wasn’t about pyrotechnics; it was just this guy with an amazing band and an incredible catalog of songs with a terrific sense of humor who really enjoyed music. It sounds crazy to say because of the career that he’s had, but I feel like in another way he was underrated because he was always there with great music — and sometimes you take people like that for granted.”

Scully, who calls Petty “one of the great rebels of the music business,” was enamored with Petty’s song craftsmanship, as well as his comedic sensibility. “One of the things that always drew me to Tom Petty — beyond the amazing songwriting and musicianship of him and the band — was that he had this great dry sense of humor, which is why people in comedy really liked him too,” says Scully. “He was genuinely funny, not only on The Simpsons. He had a recurring role on Garry Shandling’s first show, playing Garry’s neighbor. He had real comedy chops. When he did The Simpsons, I knew we wouldn’t have to tell him how to be funny; he would just come in and do it.”

“How I Spent My Strummer Vacation” was initially imagined to include guest spots with B-list rock stars, but the wish list was upgraded when the Rolling Stones expressed interest in participating to help promote an upcoming tour. “Once Mick and Keith were in, you’ve got to go after the best, and Tom Petty was literally the first person I wanted,” says Scully. “There were a few people I always wanted to have on the show, and he was one of them… It was so much fun to write his voice because I already knew it so well from all the years of seeing him play and hearing him do interviews and watching him on the Shandling show. He was just one of those guys who, on top of all the musical talent, was genuinely funny.”

There was no drama or negotiating in securing the music legend, perhaps because he had a deep affection for the long-running animated series. (He did not like to license his music frequently for TV shows, but made an exception and allowed The Simpsons to use  “The Waiting” in a 1997 episode.) “It was an easy get,” Scully recalls. “We asked, he said yes, it was that easy…. He was a genuine fan, and he kept rubbing it in to his bandmates — they had been doing an all-night recording session at the time — and telling them to be sure to remind him that he had to leave to go record The Simpsons.”

The recording session proved to be a highlight for the Simpsons producers. “He was everything we wanted,” says Scully. “He brought his guitar, he played for us. He clearly was having a great time doing it. That is him playing the guitar in the show. [At the part where Petty asks, “You just want mindless, generic rock?”] he just grabbed his guitar and asked us, ‘You mean something like this?’ and what he did was what we used in the show. He knew exactly what we were talking about. He got the joke right away. If you watch the closing credits of that episode, we have a snippet of him recording his lines and playing the guitar.” (Petty crossed paths with the show once again, presenting a gift to the Simpsons team at a 300th episode party that he attended with his son.)

“It’s a devastating loss,” sums up Scully. “It’s a loss for me personally, it’s a loss for music and a loss for comedy. Because the guy really made me laugh. This one hurts.” Ultimately, he finds solace in “How I Spent My Strummer Vacation” bringing him in contact with an idol of his. “Writing and producing that episode was definitely one of my favorite Simpsons moments,” says Scully. “It ultimately became my rock & roll fantasy camp having all these great musicians in it, but the time with Tom Petty was as cool as I could have hoped for, and more fun than I could have imagined. He did not disappoint — on any level.”

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