Circuit Q&A: Who Should Play Frank Sinatra in a Movie?


“Ol Blue Eyes,” “The Voice,” “Chairman of the Board,” “The Sultan of Swoon” or just Frank Sinatra. Whatever you choose to call him, he was and still is a cultural icon. So, finding an actor to step into his shoes and portray his life is a tall order to fill. From his sharp jawline and boyishness charm to his crooner voice and effortless swing, Sinatra was “The Man.” 

Sinatra was a larger-than-life figure whose story is filled with USO tours, mob ties, Oscar-worthy performances, The Rat Pack and famous affairs with beautiful women like Ava Gardner. Any actor who steps into this role has to be a great performer, have a decent voice and be able to pull it all off effortlessly. Musical biopics of such iconic performers can be hit or miss. So, who has the chops to play “Ol Blue Eyes?”

Leonard DiCaprio definitely has the acting chops to pull it off and we’ve seen he has the looks and effortless swag (“The Great Gatsby”), but is he too old to play the younger Sinatra during his Hollywood musical heyday? Harry Connick, Jr. definitely has the vocals, but does he have the acting prowess? Joseph Gordon-Levitt is an amazing performer, just check out his “Lip Sync Battle” performance. He can definitely nail the performer side but maybe lacks the grittier element of Sinatra’s life.

Ansel Elgort could be a perfect fit. He’s a great performer, has a smooth voice, has the swag (“Baby Driver”) and he’s a fan of the classic crooners. But can he pull off an older Sinatra? On the other hand, Ryan Gosling definitely has the verve, appeal, style and has proven that he can pull off grittier performances as well. Tom Holland is an amazing performer (again check out his “Lip Sync Battle” performance), but he could only pull off the younger Sinatra and lacks the edginess. Or maybe Chris Evans; he’s itching to do a musical, has the performer and acting chops and he could possibly pull off a convincing performance.

Who do you think has the effortless cool to play “The Chairman of the Board?” Let us know in the comments below.