October 14, 1969, was the day the New Jersey police issued a warrant for Frank Sinatra’s arrest. The warrant was in relation to his connections with the Mafia.
Sinatra got his first break in 1935 when his mother persuaded a local singing group, the 3 Flashes, to let him join. They later became known as the Hoboken Four.
Sinatra’s debut as an entertainer came in 1935 at 19, in a porn film. According to the 2011 biography of Frank Sinatra: The Boudoir Singer. They paid Sinatra $100 to appear in The Masked Bandit, wearing a mask. Once famous, Sinatra “called his friends in the mob” to stop the blue movie from ever surfacing.
Sinatra had a short-lived marriage to actress Mia Farrow. Sinatra stunned Farrow when he served her with divorce papers in front of the cast and crew of Rosemary’s Baby.
He starred in 56 movies and television specials from 1944 to 1984. These included movies The Manchurian Candidate, From Here to Eternity, and The Man with the Golden Arm. He acted in several TV shows, including the acclaimed Our Town.
He refused to play in Las Vegas hotels and casinos that would not allow African-Americans to entertain or patronize. His money-making clout that his efforts spurred increased racial desegregation in the state.
His cocktail of choice was a mix of four ice cubes, two fingers of Jack Daniel’s whiskey, and a splash of water. “This is a gentlemen’s drink,” he once said. And if you want to hold the drink like Frank, don’t touch the rim. Cup it in your hand, insulated by a cocktail napkin.
Years later, it became one of the first-ever pop music vinyl 10″ LPs. Sinatra later made classic concept albums Only The Lonely and In The Wee Small Hours for Capitol Records.

