How Bob Dylan ended up as Benicio del Toro’s one and only acting regret

Benicio del Toro has a pretty impressive résumé an Oscar for Traffic, being able to say he starred opposite Marlon Brando, even if it was in the terrible Christopher Columbus: The Discover, and a slew of memorable movie roles in the likes of The Usual Suspects, Snatch, and Fear and Loathing in Las Vegas. 

With all of that being said, the actor still has one major regret, and all he can do is look back and wish that he had accepted a role that instead he gave no second thought to, and while the movie was actually a massive flop, his regret all came down to Bob Dylan. 

The iconic folk singer is adored by many, and del Toro considers himself a big fan, so you’d think that when he was asked to star in Dylan’s film Masked and Anonymous, which he penned with director Larry Charles, he’d take up the offer without even thinking about it, yet he turned down the chance.

As it turns out, del Toro wasn’t even informed that this was a Dylan-penned film, with the musician writing it under the name Rene Fontaine, so the actor was clearly none the wiser, but it was a good thing that he rejected the role, because the thing is, Dylan might be an incredibly talented musician, but he is not a filmmaker, which marked the movie a disaster, even though it relied on a major cast, which included Jeff Bridges, Angela Bassett, John Goodman, and Jessica Lange.

Clearly, del Toro had some kind of sixth sense that this was going to be bad, very wisely stepping away from the project.

Yet, once it was released and reviewed poorly, he wished he had appeared in it after all, especially when he found out that this was not only a Dylan movie, but he would’ve also been acting opposite him, leaving him crushed. “One time, I turned down a role, and then I found out that Bob Dylan was in the movie and the scenes were with him,” the actor told EL PAÍS. 

He continued, “I would’ve loved to shake his hand, to meet him, to be able to say that I met him”. That’s a pretty frustrating thing to realise, missing out on acting alongside one of your favourite musicians. I’d be devastated, even if the film was derided by critics, because not too many people can actually say they’ve worked closely with Bob Dylan. 

In a 2012 interview, Dylan reflected on the failure of the movie, which he has come to regret. “Whatever vision I had for that movie, that never could’ve carried to the screen,” he admitted, even suggesting that Cate Blanchett, who played the singer in I’m Not There, would’ve been a better fit for his role. “Everybody was really good in it. Everybody except me! I had no business being in it, to tell you the truth,” he admitted with candour. 

Masked and Anonymous was certainly a choice from Dylan, and perhaps it was wise to use a pseudonym to write the film that wasn’t exactly on the same level as Blonde on Blonde.  

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