So the obvious question now with something like this is what actor will portray the legendary crooner? Or might it be a few different actors, seeing as Sinatra's career spanned five decades? I can't think of anyone who could pull it off. Leonardo DiCaprio's name is being thrown around as a candidate, and because he is currently Scorsese's celluloid alter-ego/muse, it would appear to be a possibility. I'd say the casting of the lead part would present one of the biggest challenges to making the film. For example, it doesn't appear as if anyone has even been cast in Chris Tucker's next film, Mr. S: My Life with Frank Sinatra. I think it's best they get some unknown, but I'm just some guy in Nacogdoches, Texas. WTF do I know??
So let's do a brief review...who has portrayed "The Voice" before?
Philip Casnoff did a really great job in 1992 playing the young crooner in the mini-series Sinatra. He was handpicked by the series' producer, Tina Sinatra, for the role. And although not obvious in this clip, he had quirks, like the thing Sinatra would do occasionally with his lower lip, down pat:
Dennis Hopper, in The Night We Called It a Day, a.k.a. All the Way (2003), captured the sort of creepy, menacing vibe Sinatra could give off during his last couple of decades, and may have proven that an Italian doesn't necessarily have to do it.
Speaking of having a creepy, menacing vibe, there was James Russo's great interpretation in the Frank, Jr. kidnapping comedy, Stealing Sinatra (2003).
The late, great Phil Hartman just nailed the cliched impression my g-g-generation had of the white toupe wearing, omnipresent tuxedo clad, mafioso thug relic/anachronism:
But, by far, my favorite impression of Frank Sinatra so far was done by a Scorsese alum, Ray Liotta, in The Rat Pack. He got to play Frank at the same point in his life as Hartman did, and he got to play Sinatra at perhaps his most swingin' period, during the heyday of the Summit. Now, I never actually believed he was Sinatra (unlike, say, Val Kilmer as Mr. Mojo Risin' in The Doors), but he has done the best job of coming close to Sinatra of what I've seen, so far: