Leonardo DiCaprio 'Can Sing Like Sinatra Man, Definitely'

When a great director and a great actor team together repeatedly, the rapport and trust between them can yield masterpieces that last generations. Think Johns Ford and Wayne (“Rio Grande,” “The Searchers”) Alfred Hitchcock and Jimmy Stewart (“Vertigo,” “Rear Window”) or Tim Burton and Johnny Depp (“Edward Scissorhands,” “Charlie and the Chocolate Factory”). Now, after several films together, Martin Scorsese and Leonardo DiCaprio can certainly be included in such a conversation – and if the duo have their druthers, they’ll be including a third legendary figure into their equation: The Chairman of the Board.

Last year, Universal Pictures and Mandalay Pictures announced that Scorsese was going to direct a biopic based on the life of Frank Sinatra, teaming with Warner Music Group and Sinatra’s estate to ensure that his song catalog could be included. Writer Phil Alden Robinson (“Field of Dreams”) is reportedly hard at work on a screenplay, and DiCaprio is one of the top choices to play Ol’ Blue Eyes.

“I don’t know [if I’ll play him],” DiCaprio told us recently when asked about the possibility, which has also been tied to such names as Depp and George Clooney. “I have no idea, really [if it will happen]. That’s really up to [Scorsese] and the people involved with [Sinatra's] estate.”

A Sinatra biopic would mark the duo’s fifth collaboration after “Gangs of New York,” “The Aviator,” “The Departed” and the upcoming “Shutter Island.” It would also be prime dramatic fodder for Scorsese and DiCaprio, considering Sinatra’s fascinating life. From the bobby-soxers years with Tommy Dorsey to his 1954 Oscar to his mob ties, sexual conquests and connection with the Kennedy administration, the man caused Dean Martin to coin the phrase “It’s Frank's world – we just live in it.”

Still, the key question remains: If Scorsese comes calling on his blue-eyed frequent collaborator, does DiCaprio have the vocal chops?

“Oh, I can sing like Sinatra man, definitely,” laughed Leo. “Can’t everyone?”

Leo as Frank: Do you see it?