The Sultan of Swoon. The Voice. Chairman of the Board. Ol’ Blue Eyes. Whatever you call him, Frank Sinatra was a bonafide talent. Not only did he have one of the most impressive music careers of all time, he also made an indelible mark on film history with his many acting roles. Whether it was jovial musicals, hard-hitting dramas or Rat Pack comedies, Sinatra could do it all. He was a one-take kind of actor and required a director who knew to let the star do his thing.

In the 1940s, Sinatra was pop idol that had young women swooning across the country. But for some reason Hollywood miscast him as the awkward type, usually matched with a more aggressive love interest and overshadowed by a big movie star like Gene Kelly.