The actor and director said Dylan would show up in the morning &34;with his hoodie on and about six bullmastiffs coming out of a VW van." Sean Penn used to box

The actor and director said Dylan would show up in the morning "with his hoodie on and about six bullmastiffs coming out of a VW van."

Sean Penn used to box with Bob Dylan: 'There wasn't a lot of conversation'

The actor and director said Dylan would show up in the morning "with his hoodie on and about six bullmastiffs coming out of a VW van."

By Emlyn Travis

Emlyn Travis is a news writer at **. She has been working at EW since 2022. Her work has previously appeared on MTV News, Teen Vogue, and *NME*.

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September 23, 2025 12:28 p.m. ET

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Sean Penn; Bob Dylan. Credit:

Karwai Tang/WireImage; Gary Miller/Getty

A hard punch's a-gonna fall whenever Bob Dylan and Sean Penn enter the boxing ring together. **

While visiting *The Tonight Show* on Monday, Penn was asked about several internet rumors surrounding him by host Jimmy Fallon, including one that he used to spar with Dylan from time to time. **

"More than once," Penn said as the audience gasped. "Bob Dylan, turns out, is a student of boxing. And I had a 16-foot punching ring at my house and I was friendly with his son. And, at some point, Jesse, his son, said to me, 'You know, my dad would like to spar.'"

Sean Penn on 'The Tonight Show'.

Todd Owyoung/NBC via Getty

And, sure enough, the* Mystic River *star said that, for about a month, Dylan would "show up every morning" at around eight o'clock "with his hoodie on and about six bullmastiffs coming out of a VW van." **

He continued, "There wasn't a lot of conversation. It was kind of like, 'Good? Good.' And we'd spar." Penn did not, sadly, mention who won the most matches in the end.**

Fallon continued his streak of putting the rumors to bed by asking Penn if it was true that he once wanted to become a stand-up comedian. "No, at one point, I wanted to challenge myself to try the terror of stand-up," Penn corrected. "And I did. And it was a terror. And it damaged the people in the audience."

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It was also true that Penn was one of the first people to ever hear Bruce Springsteen's 1982 album *Nebraska*, which takes center stage in the upcoming Springsteen biopic *Deliver Me From Nowhere*. **

"I heard it very early on because I was engaged to be married to a wonderful, beautiful young woman who happened to be his little sister, Pam," Penn said of his ex, whom he briefly got engaged to in 1982 after they met on the set of* Fast Times at Ridgemont High*.

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The director explained that he "didn't really know a lot" about Bruce and his music career until the 20-time Grammy winner sent them a demo of *Nebraska* one day.

"I heard that record and it was sort of life-changing," Penn said. "And it led to the first movie I directed eight years later because one of the songs on it was the full and total… The experience I had listening to the song 'Highway Patrolman' on that record was what became a movie called *The Indian Runner* that I made."

Written and directed by Penn, *The Indian Runner *starred David Morse as a small-town sheriff named Joe and Viggo Mortensen as his outlaw brother Frank.

Watch Penn address the internet's greatest rumors — and boxing Dylan — in the clip above.**

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