The musician who gave Jeff Bridges the “high points of my life”

“I guess I had a hard time choosing: was I an actor or a musician, or could I be both?” Jeff Bridges said of his career. Even when he was making his name known in Hollywood, music endured as his secret lover. So when he got the call to work on Masked and Anonymous, a film co-written by and crafted for Bob Dylan, the answer was easy.

It was a meeting of two beloved countercultural figures but on two very different levels. The second Jeff Bridges took on the role of The Dude in The Big Lebowski, he locked in his legacy. The character’s laid-back energy in a tale of mistaken identity seemed to connect with outsiders, and still today, it’s the character Bridges remains best known and best loved for.

In many ways, Dylan and the Dude don’t feel worlds away. The video of the spaced-out folk star trying to keep up during the ‘We Are The World’ recording session might as well have been a deleted scene as the musician could beat out anyone in a competition for the most chilled-out artist around. 

As an actor with an ongoing conflict, battling between his love for film and for music, the chance to work with Bob Dylan on Masked and Anonymous was already a dream come true for Bridges. The script was about a rock legend called Jack Fate, played by Dylan, who is bailed out of prison to perform a one-man benefit concert. It touches on topics like totalitarianism, anarchy and the future of the USA, with Bridges taking on the role of Tom Friend, a journalist trying to unmask the truth of the situation.

Really, the plot and the artistic worth of the movie were beside the point of Bridges. There was no way he was saying no to this. In a conversation with Howard Stern, he recalled how surreal it was from the start. “We shot the whole movie in two weeks,” he started. “Larry Charles wrote this thing with Dylan, and this was gonna be the first movie that he directed.” Ahead of getting to set, Bridges remembered getting a call from Charles. He remembered, “He says, ‘I consider you the head thespo, thespian, you know. Would you jam a little bit with Bob? And do some improv and stuff?” he said, still in disbelief as he added, “So I spent half a day pretending with Bob.”

But when the filming was underway, things only got more unbelievable as the music lover turned actor got the opportunity of a lifetime. “One of the high points of my life, man, is hearing *knocks* ‘Yeah?’, ‘Hi Jeff, you wanna jam?’” he said, recalling how Dylan had shown up to his trailer with a guitar, keen to play a little with his co-star.

After Stern asked Bridges if he was intimidated at all, sitting down to play guitar with one of his musical legends and idols, the actor said the answer was obvious, of course he was. “I was just in another zone entirely,” he said.

Plenty of people say you should never meet your idols. They say that the real person will never be able to live up to the version of them you’ve crafted in your head and that, more often than not, you’ll end up feeling disappointed and disillusioned. But for Bridges, who not only got to work alongside Dylan as his peer but got to hang out with him and jam on guitar, getting to know him from a closeness that few others ever could, the musician he admired more than lives up to his name.

“He was just incredible,” Bridges said, feeling like an understatement.

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