Perhaps more important than his gold trophy were Sinatra's new friends in Tinstletown. He starred in 1958's Some Came Running with Dean Martin. The two became fast friends, and the Rat Pack was born, with other "members" Sammy Davis, Jr., Peter Lawford and Joey Bishop. Known for their hedonistic lifestyle, the hell-raisers became Hollywood legends. Their films, which often reflected their propensities, include Ocean's Eleven (1960) and Robin and the Seven Hoods (1964). The Rat Pack's enduring influence is still seen today, with the resurgence of lounge lizards, cocktail music and martinis.

Sinatra's singing career benefited from his revitalized film career, too. In fact, some of his most memorable recordings followed. He released "Young at Heart" the next year. His Come Dance With Me earned him 1959 Grammy Awards for Best Album and Best Vocal Performance. Sinatra went on to win string of Grammy Awards in the 1960s, including several top honors for 1966's Sinatra: A Man and His Music and the album's hit "Strangers in the Night".

Though there have been performers with more raw talent than Sinatra, his suave, larger-than-life personality has more than compensated for any of his artistic shortcomings. And this is what has set him apart from dozens of other singers and actors. Pure charisma and an uncanny ability to connect with his audience has made the Chairman of the Board a true luminary outshone by no one.

Beth Rowen is the Entertainment Editor at Information Please.