Your Frank Sinatra Shortlist: Leonardo DiCaprio? Johnny Depp? Chris Pine? - Rolling Stone
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Your Frank Sinatra Shortlist: Leonardo DiCaprio? Johnny Depp? Chris Pine?

Kind of fitting that on the 11th anniversary of Frank Sinatra’s death, we’re consumed with his impending rebirth via the vision of Martin Scorsese. The Oscar winning director is taking the reigns of a Sinatra biopic, to be written by Field of Dreams screenwriter Phil Alden Robinson.

While there’s no word on who will try to fill Frank’s one-button shawl collar tux (or even a potential release date for the film), the mere notion of Scorsese capturing one of music’s signature voices — and one of pop culture’s most towering figures — sparked a wave of dream casting speculation and debate here in our newsroom and among our users here and over on Twitter. (Check out photos of your leading candidates here.)

It seems that most of you expect Scorsese favorite Leonardo DiCaprio to fill the role, even if you’re split as to whether or not he can pull it off. “If he pulls it off, the Oscar will [finally] be his,” h_e_n_r_y wrote here on Gimlet, however, was even less enthused, commenting “Leo was fairly rotten as Hughes [in The Aviator], a boy was cast when a man was the basic requirement. Leo looks like a child — that’s what hurts many of his attempts at more mature characterizations.”

In the Leo vein, many users are suggesting Scorsese look to Hollywood’s A-list to step into Frank’s larger than life persona. On Twitter, @BenjaminFBurns pitched Sean Penn, Brad Pitt or Johnny Depp, while @chile_pepper put her money on Sinatra devotee George Clooney (who certainly has the swagger, and already jacked Frank’s role in Ocean’s 11). A few even suggested Scorsese’s Bringing Out the Dead partner Nicolas Cage.

Scorsese and Universal have full access to Sinatra’s music through Frank Sinatra Enterprises, but many still suggested musical chops were essential to landing the role. “Harry Connick Jr. … He can nail the music easily and he has the acting skills as well,” ttrfanatic wrote on our site. And perhaps throwing back to Sinatra’s initial bobby-soxer appeal, teen pop was served among our commenters as well. On Twitter, @Caitlin_Mullen suggested boy band grad turned pop renaissance man Justin Timberlake, while among our commenters, davids suggested Zac Efron (though he doesn’t seem like Ava Gardner’s type).

The suggestions ran the gamut from X-Men Origins: Wolverine star Taylor Kitsch to Ryan Phillipe to Vince Vaughn to Val Kilmer. But five suggestions were intriguing enough to rise above he rest:

• Chris Pine: He’s got the eyes, and demonstrated in Star Trek that he’s got the fire. Plus, that boozy barroom beat down he suffered in front of Uhura proves he has at least one piece of the Sinatra mystique down.

• Ben Affleck: @whoisfluffy suggested the State of Play star with an LOL on Twitter, but we aren’t laughing. Anyone who saw him explore the dark underbelly of TV’s Superman, George Reeves, in Hollywoodland has to be curious about how he’d handle Sinatra.

• Michael Imperioli: This one came in from an anonymous commenter, and while Imperioli might not look the part, he certainly knows the character — a skinny Italian kid from north Jersey with a chip on his shoulder and dreams bigger than the town he grew up in. Come on, it’s right up his alley.

• Matt Damon: The laughingly named “Matt Damon’s Agent” suggested Jason Bourne as Sinatra, but the suggestion has gathered enough steam on various sites that it bears some thought. Damon might be able to tap into Sinatra’s boyish charm and bare-knuckled approach to problem solving, but can he command a stage?

• Edward Norton: @HollySWood sent us this one via Twitter, and it certainly seems like doing time as David Banner and The Hulk would help Norton to channel Sinatra’s more volatile moments.

Ultimately, we’re inclined to agree with those of you who suggested no one actor can fill Frank’s shoes. So how about the same treatment Bob Dylan received in I’m Not There — multiple actors, each representing a different moment in his life? Could work (if they can sort out who gets top billing).

So what do you think? Who should slip on Sinatra’s fedora?


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