Sinatra is a bit of an enigma. There is no getting around it: Frank was cool. Frank made sure that everyone knew he was cool. Frank got his first breaks in showbiz because of his mother’s influence, and he was still cool. When his career started to take a nose dive, he attempted suicide, and Frank still managed to be cool.
Frank Sinatra was an incredibly talented singer and showman, and that is what ultimately made him cool.
Frank was born in 1915, the only child of Italian immigrants. His father served as a Captain in the Hoboken Fire Department, and his mother was active in Democratic Politics. Little Frank began singing “professionally” at the age of eight, standing on a bar top and singing for tips.
Young Frank Sinatra was invited to leave high school after just 47 days because of his rowdy behavior. He supported himself as a newspaper delivery boy and later as a shipyard riveter, but music was his calling. He listened intently to swing jazz, but never learned to read music. In 1935, Mama Sinatra convinced a local group, the Three Flashes, to become the Hoboken Four. The group appeared on Major Bowes Amateur Hour and was voted first prize.
In 1939, Frank signed a one year contract with the Harry James Band. Before the year was out, James allowed Sinatra to move on to Tommy Dorsey’s Band. Dorsey had Frank sign a contract that awarded the band leader one third of the singer’s earnings in show business. (It was later rumored that the contract was bought out for a few dollars by mob-boss Sam Giancana. The incident was fictionalized in The Godfather.)
The exposure from singing with the Tommy Dorsey Band put Sinatra on the top of the music industry polls, and suddenly his records were in demand by teenage “bobby soxers”. This was a major shift for the record industry, records had always been marketed to grown-ups before.
The Musician’s Strike of 1942-44 helped to fuel Sinatramania, along with a few lucrative radio gigs. His first starring vehicle was on CBS’s 15 minute Songs By Sinatra, starting in late 1942. In Feb, 1943, he became the featured singer on Your Hit Parade. A budding movie career led to appearances on Lux Radio Theater and Screen Guild Theater. His growing popularity made him a popular guest for the radio comedians like Bob Hope, Fred Allen, Bergen and McCarthy and Jack Benny. He was also welcomed on the programs of other popular singers like Bing Crosby, The Andrews Sisters and Dinah Shore.
Frank appeared on a number of AFRS programs during the War, such as Command Performance, GI Journal and Mail Call. However, some who served have related that Frank himself was not well loved, even resented by the troops. Frank was seen by the troops making lots of money and surrounded by pretty girls back home. He was 4F because of a ruptured eardrum, but there were persistent rumors that Sinatra bought his way out of serving (rumors that are thought to have started in reaction to his Democratic Politics).
In 1950, Frank’s vocal cords began hemorrhaging on stage, and he began to realize that the teenagers who used to swoon for him were moving on to younger idols. He made a couple of less than successful forays into television.
His career began to rebound with a supporting role in From Here to Eternity in 1953. The same year he returned to radio, this time in a dramatic role as Rocky Fortune. Fortune lasted for a single season. It was the story of a temp worker/ jack-of-all trades who weekly stumbled upon a situation that required his amateur crime-fighting prowess. The program benefited from great writing and the time slot immediately following Dragnet on Tuesday nights.
In the mid-fifties, Sinatra became part of the Holmbly Hills Rat Pack, a group centered around his drinking buddy, Humphrey Bogart. After Bogart’s death, the group began to orbit around Frank and his Las Vegas buddies, notably Dean Martin and Sammy Davis Jr.
A lifelong Democrat, Sinatra changed his politics after being snubbed by President Kennedy. The President had been invited to stay at Sinatra’s estate during a West Coast visit; however, the Justice Department had reservations because of Frank’s supposed mob connections. Kennedy enjoyed the hospitality of Bing Crosby in Palm Springs, and Frank moved his loyalty to the GOP.
You can get away with that sort of thing when you are as cool as Frank Sinatra.