Who Could Play Frank Sinatra?

Johnny Depp

Qualifications: He’s versatile, and Sweeney Todd proved he could sing (still, they’ll likely dub in the songs).

Depp’s always up for a challenge and he does bear a passing resemblance to Ol’ Blue Eyes, even if he has, er, brown eyes (but that’s what contacts are made for). Plus, he brings huge star/box-office appeal…

Problems: …which most likely isn’t what Marty Scorsese will be after.

He’s taken chances on young unknowns before and with the Sinatra name and songs attached, this is one film that could promote itself without too much cranking of the star wattage.

Leonardo DiCaprio

Qualifications: You mean, aside from the fact that Scorsese has used him in almost all of his recent films? The pair have established a serious rapport and Marty has already slotted Leo into one real-life story ( The Aviator ).

Plus DiCaprio has the easy charm and looks to pull off a Sinatra turn.

Problems: Like Depp, he’s also a little over-exposed and chances are audiences may see that nice Mr DiCaprio instead of the Chairman Of The Board.

Matt Damon

Qualifications: He looks more like Frankie than many of the other contenders, and he’s got proven singing talent.

He’s also able to submerge himself into parts, which could see him vanishing into the role and subverting the extreme famousness factor.

We’re also betting he could cope with a wider range of Sinatra’s life, depending on how much of it Scorsese and writer Phil Alden Robinson plan to show.

Problems: He’s still a famous face, despite that chameleonic ability.

And while Damon could easily handle the bare-knuckle bruiser side of Sinatra’s life, we’re not 100% convinced he’s got the burning fire of authority to command attention when Frank takes to the stage.

James Franco

Qualifications: Despite appearing in some recent major movies (the Spider-Man franchise, Milk , Pineapple Express ), Franco is still not a big star/leading man – which could work to his advantage.

Also, the eyes have it – he could clearly channel Sinatra with just one gaze.

Problems: He’s got the looks, but he’d have to work at the attitude.

And he might be a little too young - again, depending on Scorsese's time-frame. Still, could be a job for the Benjamin Button make-up folks...

Chris Pine

Qualifications: He’s just rocketed himself into the stratosphere as Captain Kirk in Star Trek – but he’s not a movie star just yet.

Which is why he could be ideal – he’s clearly able to pull off a multilayered role that spans both Smooth Operator and Brawler, and, like Franco, he definitely has the eyes.

Problems: Too young, too slight.

Still, Marty might go down a sort of I 'm Not There route - using different actors for different stages of Sinatra's life. Pine would be pretty much pre-loaded as Early Frank.

Harry Connick Jr

Qualifications: He’s certainly qualified in the crooning department.

And while he’s dutifully kept up with the acting game, he’s never exactly been a huge star, which means he could play Sinatra without the baggage.

Problems: We doubt he’s the level of thesp that Scorsese would feel comfortable with.

He might have the pipes, but he doesn’t display the chops very often and usually comes off a little too stiff to play one of the smoothest crooners to walk the Earth.

CG Sinatra

Qualifications: Doesn’t need a big trailer. Doesn’t need a big salary.

Yes, we mean hire a total unknown, shove a blue mask over his noggin and layer on a CG Frank for most of the running time.

If Brad Pitt can play a crinkly baby thanks to computer trickery, then surely Frank can come back to digital life.

Problems: Cheap on salary but the techniques would cost a fortune. Might be too distracting - and it's more Cameron than Scorsese.