Sean Penn Reveals He Used to Box Regularly with Bob Dylan

Sean Penn and Bob Dylan have a surprising connection.

Penn, 65, appeared on The Tonight Show on Monday, Sept. 22 to promote his new movie One Battle After Another. During his interview with host Jimmy Fallon, Penn said he and Dylan, 84, sparred “more than once” as Fallon, 51, asked Penn to confirm or deny various rumors about his life.

“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,” Penn said, when Fallon asked him to expand on his boxing adventures with the folk-rock icon. “And at some point, Jesse, his son, said to me, ‘You know, my dad would like to spar.’ ” (Dylan shares son Jesse, 59, as well as children Maria, 63, Anna, 58, Sam, 57, and Jakob, 54, with his ex-wife Sara Lownds, as well as daughter Desiree, 39, whom he shares with ex-wife Carolyn Dennis. 

“Sorry Bob, if I’m talking out of school, but he would show up every morning,” Penn added. “That went on for about a month, I think. About seven or eight o’clock in the morning, with his hoodie on and about six bull mastiffs coming out of a VW van. There wasn’t a lot of conversation, it was kind of like ‘Good? Good.’ And we’d spar.”

Dylan, the singer-songwriter behind 1960s hits like “The Times They Are a-Changin'” and dozens more, is apparently a major boxing fan. Ben Stiller once told Fallon during a 2022 Tonight Show interview that he used to attend sparring sessions at a gym Dylan owned in Santa Monica, Calif. 

While Penn did not elaborate further on his experiences boxing with Dylan while speaking with Fallon, he also confirmed that he once tried out stand-up comedy and that he heard an early version of Bruce Springsteen’s 1982 album Nebraska.

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Penn takes to the big screen as a menacing military officer in One Battle After Another, which also stars Leonardo DiCaprio, Regina Hall, Benicio del Toro, Teyana Taylor and newcomer Chase Infiniti. The movie follows Penn’s character as he hunts down former members of a militant revolutionary group in California, including DiCaprio’s lead character Bob Ferguson, 16 years after Bob goes into hiding.

One Battle After Another is in theaters Sept. 26.