Bob Dylan and Sean Penn may seem like an unlikely pair, but they bonded over a shared hobby.
The actor, 65, revealed during his Monday, September 22, appearance on The Tonight Show Starring Jimmy Fallon that he and the singer, 84, used to box together.
“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 recalled. “And at some point, Jesse, his son, said to me, ‘You know, my dad would like to spar.’”
Dylan is a father of six. He shares Maria, 63, Jesse, 59, Anna, 58, Sam, 57, and Jakob, 55, with his ex-wife Sara Lownds and Desiree, 39, with ex-wife Carolyn Dennis. Jesse, for his part, likely runs in the same circles as Penn because he is a film director and production executive.
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After Jesse mentioned the idea to Penn, the One Battle After Another star and Dylan became regular sparring partners.
“Sorry, Bob, if I’m talking out of school, but he would show up every morning,” Penn continued. “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 Bullmastiffs coming out of a VW van. There wasn’t a lot of conversation, it was kind of like, ‘Good? Good.’ And we’d spar.”
Ben Stiller previously shared Dylan’s passion for boxing during a February 2022 appearance on The Tonight Show, revealing that the Grammy winner owned a gym where several celebrities boxed, including David Duchovny, Garry Shandling and Ray Mancini.
However, Stiller, 59, noted that he never expected to spar with Dylan at the gym, confessing that he was starstruck by him.