The Chairman of the Board, Ol’ Blue Eyes, The Sultan of Swoon are a few of the honorifics that Francis Albert Sinatra earned over his legendary career. He weighed a whopping 13 pounds when he was born in Hoboken, New Jersey today in 1915. His large size at birth made his delivery a complicated one which left Frank with a broken ear drum for the rest of his life. In spite of this his singing career produced over 1,400 recordings and 31 gold, nine platinum, three double-platinum and one triple-platinum albums.

Sinatra was influenced by the big band jazz music that was popular during his youth and was especially fond of Bing Crosby. He joined his first singing group, The Hoboken Four, in 1935 and had some success on the radio. In 1939 he became the singer for Tommy Dorsey’s band and was paid $125 per week. By 1946 he was making over $90,000 per week.

His career would soon come crashing down as rumors of Mafia connections and an affair with Ava Garner damaged his reputation. By 1952 he had been dropped by his record label and was playing county fairs and small shows in Las Vegas. Down but not out, Sinatra kept working and was soon back on track after he appeared in the movie From Here to Eternity in 1953. He won an Oscar for Best Supporting Actor and he was soon again in demand.

By the 1960s, Sinatra established residency at Caesar’s Palace and formed the Rat Pack along with Dean Martin, Joey Bishop, Sammy Davis Jr. and Peter Lawford. The Rat Pack epitomized the swinging, boozing, skirt chasing and gambling lifestyle and looked super cool while doing it. They appeared in number of popular movies including Ocean’s Eleven in 1960. In 1966, Sinatra topped the singles chart with “Strangers in the Night”. Frankie was back, baby.

Sinatra continued working as he pleased for the rest of his career. In 1993 he released the “Duets” album which debuted at #2 on the album chart and sold over three million copies. The following year he released “Duets II” which hit $9 on the album chart and sold over one million copies. Nearly sixty years after he started, Sinatra was still a major musical force.

Sinatra’s life was full of contradictions. A champion of civil rights, he led the movement to desegregate the hotels in Las Vegas, all while slinging racial jokes at Sammy Davis Jr. on stage. He was friends with John Kennedy and Ronald Reagan as well as mobsters like Sam Giancana, Bugsy Siegel and Lucky Luciano. Sinatra was a practicing Catholic that had been divorced three times and had numerous affairs. Despite all this, Sinatra remains one of most beloved musical icons in American history.

“Luck Be a Lady” 1965:

“Summer Wind” 1966:

 “The Girl from Ipanema” 1967: