In the early 30s, Frank Sinatra dropped out from high school and joined a group of vocalists before touring with band-leaders such as Harry James and Tommy Dorsey to whom he lent his seductive crooner voice. By 1942, the skinny, big-eared Italian-American kid had provoked a veritable 'Sinatramania' and his live performances caused riots. World War II helped the singer impose himself as, not able to serve in the army, he trusted audiences and media’s attention while becoming the obsession of lonely women. Increasing his domination on the world of entertainment, Frank Sinatra also appeared in numerous films such as Anchors Aweigh, in 1945. However, suddenly, a combination of damaged vocal cords that roughened his legendary velveteen voice, reputed ties to organized crime, cinematographic flops and a torrid romance with Ava Gardner ended his reign by the 1950s. Yet, he was reinvigorated by the success of the film, From Here to Eternity and in 1953 and Ol' Blue Eyes was back. He, therefore, reinvented himself as a vocalist. Celebrating in a way his resurrection, Frank Sinatra conducted a larger than life existence with his celebrity buddies, the Rat Pack that mingled business and pleasure just as their Ocean's Eleven film proved, in 1960. During the 1960s, he married the young and waifish Mia Farrow and was provided with his legendary anthem, the hit, My Way, in 1969 while his voice resonated in space when Apollo XI's astronauts listened to Fly Me to the Moon. From the 1970s, the crooner began tiring but did continue performing until the middle of the 1990s. The Voice remains an iconic performer, one of the most impressive and magnetic figures of entertainment, remaining a legend long after his death. And, like most legends, Frank Sinatra is a paradoxical figure in the likes of Marlon Brando or Pablo Picasso, full of contradictions: singing charming romantic tunes when a renown misogynistic and hanging out with the president of the United States as well as the mafia. In a way, the bad boy from New Jersey had never quite disappeared.