Frank Sinatra
The first, and possibly the greatest American musical superstar, Frank Sinatra was inarguably one of the most successful, multi-talented entertainers of the 20th-Century. Starting out as a crooner with bandleaders like Tommy Dorsey in the late-1930s, by 1942 "Sinatramania" had swept the country and his live performances were causing riots. Just as suddenly, a combination of damaged vocal cords, reputed ties to organized crime, and a torrid romance between the still married Sinatra and actress Ava Gardner conspired to end Sinatra's reign by 1950. In one of the most incredible career resurrections of all-time, he reinvented himself with an Oscar-winning performance in "From Here to Eternity" (1953), followed by a string of era-defining hit records with Capitol, such as Come Fly with Me! and Frank Sinatra Sings for Only the Lonely. Sinatra cultivated his larger-than-life persona with his celebrity buddies, the "Rat Pack," who were immortalized in the hip crime-comedy "Ocean's Eleven" (1960) and rubbed shoulders with the likes of President John F. Kennedy. Always eager for new challenges, he founded his own record company and earned more rave reviews for roles in films like "The Manchurian Candidate" (1962). Although he retired briefly in the early '70s, Sinatra returned soon after to thrill longtime fans with more sold out concerts and chart-topping albums like 1993's Duets, right up until his 80th birthday. Over the course of his 60-year career, Sinatra elevated popular music to an art form while he attained the status of legend - the Chairman of the Board.