Who better to direct a biopic about the famous blue-eyed Italian-American entertainer Frank Sinatra than Martin Scorsese? This is the kind of movie news that's so "just right" it makes me wonder why it hasn't happened before. Here's more on the project, titled simply, Sinatra:
The deal comes after years of negotiations with Frank Sinatra Enterprises, a joint venture of the crooner's estate and Warner Music Group. One major obstacle was the internal politics of the estate, where family members had to come to consensus on how to tell the story and, more importantly, just how much of the story to tell.
Raised during the Depression, [Sinatra] built a singing career that weathered many changes in popular culture, all while he racked up 31 gold records and countless other honors. He also had a successful career as an actor, proving naysayers wrong by earning an Oscar for From Here to Eternity. His personal life was just as eventful. He suffered from depression and a bipolar disorder, was alleged to have connections to organized crime and was married four times, including to actresses Ava Gardner and Mia Farrow.
Now the big question remains: What modern-day actor can appropriately portray Sinatra, one of America's most famous singers? Who's got the charm and presence, a bit of an edge at times, and most of all, those mesmerizing eyes? Who would you cast?

















Calida
Irregular Choice
Lancaster
He sort of looks like Bruce Willis if Bruce got leaner, but Bruce would NEVER be able to play him.
1Leo Dicaprio, Aaron Eckhart, Jude Law
2Leo!
3oh man.....i'm so excited...this is tough.
leo-obviosuly he would be great, but its weird since he already played howard hughes. howard also had a thing for ava gardner.
i don't know how good of an actor he is, but i have a major crush on Chris Pine and his pretty blue eyes. I haven't seen Star Trek yet or anything else he's been in.
i think aaron eckhart has the enough of the rugged-yet-handsome look to play him.
4Leo, since Scorcese is already obsessed with him. But Leo would have to drop alot of weight. He needs to anyway.
5Ray Wise, the devil from Reaper, he's already doing a great job copying his style on that show
6Leo would be good.
I also think that perhaps Matt Damon could play him if he lost
about 30 lbs.
7Leo is too piefaced to play Frank.
8Chris Pine actually DOES kind of look like him in the tres sugar do dump marry poll. My new vote is Chris Pine!
9Sinatra at what age though? And will he need to be able to sing?
10Leo!
11random thoughts, but frankie muniz? although i agree that leo would be great, and scorcese loves him.
12Maybe not a match in the looks category but Michael Buble definitely has the singing down!
13All I can think is Ed Harris, but Ed would look so wrong with hair. Well, maybe not the slicked-back Sinatra look. Chris Pine is way too young, no?
14LEO! That guy deserves an Oscar so much!!
15Di Caprio but if they need a singer then Buble
16LEONARDO DECAPRIO THATS A GIVEN !!!!!!!!!
17DI CAPRIO LOL my bad
18I'm sorry but to say Leo makes me...
19Hugh Jackman, great eyes and can sing, but he is really too big of a man (size wise)...
I think you are going to have to go with unknown or someone who had not make their mark yet in another role...
20I'm not surprised that so many people are saying Leonardo DiCaprio because of his association with Scorsese. However, it won't happen. Leo will be portraying Teddy Roosevelt in another Scorsese film. Not saying that the Sinatra film won't be made--just not Leo as Sinatra.
And as redhick152 mention--he played Howard Hughes already. Leo does not strike me as someone who would sign up for a somewhat similar role.
21Maybe Leo with Michael Buble's voice
22This is tough. And I'm at a total loss.
23So Howard Hughes is similar to Sinatra? haha not really!
24Then Michael Buble. He's the total package.
25James Franco!!
26Totally going out on a limb here, but what about Robert Downey Jr or Hugh Jackman? (The former can morph, the latter can sing.)
27Ray Liotta
) if Frankie was bi-polar RL is good at crazy...and intense...but Buble is
good with the songs...I am excited about seeing it!
28Harry Connick Jr!
29@LaurenG22
L2R and Nooooooo leo will not hook up with u bc he has a GF! Duh!
30Harry Connick Jr. looks like Sinatra.
31leo is greasy with man boobs. gross.
32This is hard! Leo would rock the part, as would Downey. Frank is alot different than Hughes, I don't see how they would be similar characters.
33Frankie Muniz is a cool choice, as long as he could pull it off.
I'll watch Jude Law in anything, so I'm biased on that one.
Ray Liotta is too old now, but Harry Connick might work.
I immediately though Leo too, but I could see James Franco in the part as well!
34Harry Connick Jr. would be a much better Sinatra than Leo. The guy can not only sing, but actually looks more like Sinatra than Leo. Enough of this "Leo Leo Leo OMG LEO" /rolls eys.
35Thanks for the Anonymous post ability Sugars, its great having them come in and crap all over a light hearted discussion.
36how has no one said Clooney yet? He was the first person to pop up in my head.
37I second the Michael Buble choice!
38Michael Buble would be a good choice! Sheesh lighten up Jinx.
39James Marsden, for sure. He's got the eyes, the cheekbones, AND he can sing!
40My vote goes to Michael Buble or Harry Connik jr. Leo hasn't done anything good since his Growing Pains day.
41It depends on what period of Frank Sinatra's life they'll focus on I'd say - unless they try and fit it all in, I'd imagine it'll be the earlier years. I actually thought of Chris Pine for likeness, but have no idea as to whether he can sing. I think Jake Gyllenhaal would have a very good chance - think he was down for the final auditions for Moulin Rouge - so he must have a note in his head.
42Leo hasn't done anything good since Growing Pains???? I assume you've only seen "The Beach" since Growing Pains, then?
43
mama!
44James Franco. Oh yes.
45My Leo.
46Matt Damon or Dennis Quaid
47it's about time; if anyone ought to have a biopic of his life, it's Frank. he is an absolute gem in music history. as for casting, I actually hope it's not someone famous. I always find that someone well known distracts from the story...
48I like the Chris Pine suggestion, but only if he can sing. He's definatley got the looks.
49The best choice, to me, would be Robert Downey Jr. He is an inspired mimic and he can sing and dance, and he's the right size. He knows how to do fierce and charming at the same time.
Jude Law is also gifted - might be a great role for him too.
Daniel Craig would be quite good, I think.
With great makeup, maybe Ryan Gosling?
Hey, how about Don Cheadle in white face?? there's a stretch, but he is super talented.
Slim down Alec Baldwin and he would be an excellent frank - he's got the "mafia" genes, but I don't think he can sing.
Not leo - he doesn't have frank's essence.
50Maybe Clooney, but it would be a lot of work to keep the "clooney" vibe out.
Actually, I'll bet Damon could pull it off.
But of everyone, Robert Downey jr. is the best choice, i think.
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