1. Frank Sinatra
Chairman of the Board. King of the Rat Pack. Old Blue Eyes. The name Sinatra is synonymous with cool and you cant talk about music without mentioning him somewhere in the conversation. While he was busy building one of the most enduring legacies in music (sorry, Im gushing), he was also winning a Best Supporting Oscar for his role in From Here to Eternity (1953), earning a Best Actor nod for his role in The Man with the Golden Arm (1955), and holding his own with screen legends: Cary Grant (The Pride and The Passion), Natalie Wood and Tony Curtis (Kings Go Forth), Steve McQueen (A Hole in the Head), Marlon Brando (Guys and Dolls), and Gene Kelly (On the Town). Lets be honest, with a shining example like this, lesser efforts by other singers ((cough) Rihanna in Battleship, Will.i.Am in Wolverine) are just criminal. Anyway, when it came to Sinatras films, like he said in the song, he did it his way.