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Tom Petty and Bob Dylan announced they would be teaming up for Dylan’s 1986 True Confessions Tour. The announcement was memorable because two major forces in the music industry would be working together for a lengthy period of time. It also stuck out to people because Petty and Dylan wore heavy makeup during the press conference about the tour. When asked why, they didn’t have much of a reason.

A black and white picture of Tom Petty and Bob Dylan posing in front of a wood paneled wall.
Bob Dylan and Tom Petty | Michael Ochs Archives/Getty Images

Tom Petty joined Bob Dylan on tour in the 1980s

Petty and the Heartbreakers served as Dylan’s backing band at Farm Aid in 1985, and the show went over well. So well, in fact, that Dylan wanted the band to join him on tour

“So we backed him up at Farm Aid and it went really well,” Petty said, per American Songwriter. “And then afterwards in the trailer, Bob came back and said, ‘Hey, what would you think of doing a tour? I’ve got a tour of Australia I want to do, and what would you guys think of doing that?’ And we’d all been huge Dylan fans, and we were very intrigued by the idea of playing with Bob.”

Initially, they’d only planned to perform with Dylan in Australia, but they extended the tour.

“So off we went. And that went on for two years,” he said. “We’d do part of it and then more would get added on, and then more would get added on. We really did the world with Bob Dylan.”

They announced their tour while wearing heavy makeup

Petty and Dylan spoke about the tour in a 1986 press conference. When they stepped out, they surprised journalists with their appearance. Per the Glasgow Evening Times (via The Petty Archives), Petty wore “deathly white foundation, heavy duty mascara, and lots of baby pink highlighters.” Dylan opted for a cakey layer of orange tanner that made him look “like a baked bean.” 

With the stark white foundation, it may have seemed like Petty was referencing Dylan’s face makeup from his 1975 Rolling Thunder Revue tour. It seems, though, that the looks could be chalked up to boredom.

“We were stuck backstage for over an hour and we just got bored,” Petty said. “So we just let the makeup artists get on with it because we had nothing else to do.”

Bob Dylan didn’t want to stop touring with Tom Petty 

The tour was successful, and the Heartbreakers were an exciting backing band for Dylan. Eventually, though, they had to get back to touring on their own. 

“I remember telling Bob, when we were in England at the end of the tour, that we were going to have to stop, as far as backing him up,” Petty said in the book Conversations With Tom Petty by Paul Zollo. “I had to go back and sort out my life and my family, and find a home, and we needed to get back to just being The Heartbreakers. And we had really enjoyed it, and now he needed to get his own band, because we needed to get back to our own thing.”

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Dylan wanted to keep touring and tried to convince Petty to stay

“Bob said, ‘No, we don’t want to break this up, it’s too good,'” Petty explained. “And I said, ‘It is really good, but we kind of had our own agenda before we got into this.’ And he thought we could do both.”

Ultimately, though, the joint tour had to come to an end. Luckily, it wasn’t the last time Petty and Dylan collaborated. They would reunite shortly after in The Traveling Wilburys.