The Oscar winner who taught Bob Dylan how to act: “Go and do some improvisation or something”

Having been so distinctively and uniquely famous for so long, Bob Dylan would never be the type of performer who’d disappear into a role whenever he tried his hand at acting.

Of course, cinema history has been littered with musical artists who’ve appeared in countless movies playing a variety of characters and seamlessly swapped the stage for the silver screen, but Dylan’s credits have been sparse and few and far between.

He made a brief cameo as a chauffeur in 1999’s Paradise Cove, went uncredited as an artist in Dennis Hopper’s troubled Catchfire, virtually disowned the semi-autobiographical Hearts of Fire, and in terms of nothing but performance, was at his most memorable in Sam Peckinpah’s Pat Garrett and Billy the Kid.

Jennifer Hudson, Frank Sinatra, Cher, and Barbra Streisand are just four of the singers and musicians who won Academy Awards for their acting exploits, but Dylan was hardly interested in becoming one of their number. That said, he was evidently invested in 2003’s Masked and Anonymous, seeing as he co-authored the screenplay under the pseudonym of Sergei Petrov alongside director Larry Charles.

Backed by a heavyweight supporting cast that included John Goodman, Penelope Cruz, Jessica Lange, Angela Bassett, Bruce Dern, Val Kilmer, and more, the dramatic burden didn’t fall on his shoulders. That said, Charles still required a convincing performance, which is where top-tier thespian and Dylan superfan Jeff Bridges came in.

“Why don’t you and Bob go off and you teach Bob some acting?” Bridges recalled the filmmaker’s instructions to The Guardian. “Go and do some improvisation or something. He was so great to work with. He’s such an incredible actor. I mean his presence, right?”

Try as he might, though, it’s debatable as to whether Bridges succeeded in his task. Dylan didn’t have to stretch himself too much playing Jack Fate, a legendary musician who gets bailed out of prison to headline a concert to safeguard the future of American society, but the line between a passion project and a vanity project is awfully thin.

Unfortunately, Masked and Anonymous fell into the latter camp, and it’s one for the diehard fans only. Still, Bridges couldn’t have been happier that not only did he get the chance to work alongside one of his idols, but he also had the opportunity to jam with them, which would have been a pinch-me moment for a star who always dreamed of making it in the music industry before committing to acting.

Whether or not he actually managed to give Dylan any valuable pointers on how to perform in a feature film context doesn’t really matter when Masked and Anonymous wasn’t designed to appeal to the mainstream. Dylan got what he wanted out of it, and so did Bridges, which was more than enough for the latter.