September 24, 2025
Bob Dylan appeared to be a major boxing fan, as Sean Penn shared he would show up at his home regularly to spar.
On the Monday, September 22, episode of The Tonight Show on Monday, Penn paid a visit to promote his new film One Battle After Another.
During the conversation at the late-night show, the 65-year-old actor spilled secret bond he and Bob Dylan had, sharing they were ring buddies and used to spar together — "more than once."
"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 told Fallon of his spar with the rock icon.
"And at some point, Jesse, his son, said to me, 'You know, my dad would like to spar.' "
Penn further shared that Dylan then started coming over regularly.
"Sorry Bob, if I'm talking out of school," he apologized to Dylan if he was oversharing about his personal life, noting he would show up every morning for about a month.
"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," Penn added.