Leonardo DiCaprio has been tapped to play -- but not sing -- Frank Sinatra in Martin Scorsese's biopic about the crooner as reported by The Hollywood Reporter. Anthony Bruno from truTV has the extensive story on "Frank Sinatra and the Mob":

Even if Sinatra wasn't a criminal himself, he certainly knew plenty of criminals and considered many of them good friends. Despite his denials, year after year, evidence piled up indicating that Sinatra enjoyed a very special relationship with the Mafia. * * * The record shows that Sinatra's relationships with known mob figures were often more than just casual meetings with fans. He performed in clubs and theaters controlled by the Mafia. He made investments with mobsters. He used his status as a celebrity to make requests on their behalf—all the way to the Oval Office in one instance. He hosted men of honor at his home, at his hotels, even at his mother's home. He apparently valued their company as much as they valued his, and if he publicly chafed at being tarred with the Mafia brush, he often used his gangland veneer to instill fear and respect on his late-night romps in the "wee small hours of the morning."

http://www.trutv.com/library/crime/gangsters_outlaws/cops_others/frank_sinatra/1.html

http://fivefamiliesnyc.blogspot.com/

He did it his way. Love and marriage to the mob. Their chauffers would drive. It was that old black magic. That old devil moon.

if DiCaprio will be Sinatra, then Matt Damon should play JFK and Mark Wahlberg should play Lucky Luciano. if they make a movie about JFK's life Damon should play him. and if they make a modern movie on Luciano's life, then Wahlberg should play Lucania. i can see Damon as JFK hes from Mass and with the right make up he would look like him. the same thing with Wahlberg, he resembles Lucania, in the eyes and shape of mouth and face. hopefully we will see some mob activity in this Sinatra movie, like the back stage picture with all the bosses that "the men just suddenly gathered around him, and he didnt know who they were" yea.... and Abe Reles thought that he was Superman, and jumped out on his own.... same reality there.