“Frank Sinatra was arguably the most important popular musician of the 20th century” (Ruhlmann), rivaled only by Bing Crosby, Elvis Presley, and the Beatles. Through his ability to make classics from his interpretations of others songs, Sinatra survived ‘50s’ rock and ‘70s’ punk, winning over new fans while retaining a loyal, if aging, group of aficionados. Besides recording nearly 1,500 songs, Sinatra starred in nearly 60 motion pictures (many with his Rat Pack buddies). His turbulent personal life and tough-guy posturing also made him a well-known media figure.
Sinatra was the only child of Italian immigrants. He concentrated on athletics (most notably boxing) and getting into scraps with other boys and the local police. He worked after school at the local newspaper, rising quickly from copy boy to rookie sports reporter, often covering high school games in which he participated.
He dropped out of high school to pursue music, a move partially inspired by a 1933 Bing Crosby concert. He worked locally in clubs and bars.
From Bowes to Dorsey
With the Hoboken Four, Sinatra won a 1935 Major Bowes Amateur Hour contest that led to concert dates with the Major Bowes travelling show, along with club and occasional radio dates. In 1939, shortly after marrying childhood sweetheart Nancy Barbato, Sinatra was hired as a vocalist by Harry James, a trumpeter who left Benny Goodman to start his own big band.
In 1940, Sinatra was recruited by Tommy Dorsey, leader of one of the most popular swing bands. The combination recorded 16 top ten hits, including the chart-topping, Grammy Hall of Fame song I’ll Never Smile Again.
Sinatra learned breath control, in particular circular breathing, from Dorsey. Sinatra later adopted jazz phrasing, which greatly enhanced his rhythmic style. More than any other previous popular singer, Sinatra learned the value of delayed phrasing and singing behind the beat, and he and his arrangers invariably found exactly the right tempo. His relaxed rhythmic style contrasted strikingly with the stiffer-sounding singers who preceded him. Even Bing Crosby later used some of Sinatra's stylistic devices. (Crosby never fully shook off his lazy-sounding, 2/4 style until late in his career, while Sinatra, almost from the start, was completely comfortable with the 4/4 beat of swing).
In 1942, Sinatra struck out on his own, quickly becoming an idol to hordes of teenage girls. His first chart entry under his name was Cole Porter’s Night and Day, a song which also marked his first credited appearance in a motion picture. He was paired with Gene Kelly in 1945’s most successful film – Anchors Aweigh.
By 1946 Sinatra was selling as many as 10 million singles a year and playing packed houses coast to coast. In 1947 Sinatra recorded 72 new songs, a personal high mark; he was making almost a million dollars a year at a time when a new car cost around $1000.
The Tough Guy Persona
Unfortunately, Sinatra became the subject of serious allegations about his personal allegiances: in February of 1947 it was reported that he spent time in Cuba with mob boss Lucky Luciano and in April he was accused by a Hollywood gossip columnist of having ties to the Communist Party. Sinatra denied these charges, claiming he was the subject of anti-Italian prejudice, but rumors continued to dog him. In 1949 the Committee on Un-American Activities claimed that Sinatra had ties to both the Mafia and the Communists; that same year he was further disgraced when his affair with actress Ava Gardner was exposed and his wife Nancy separated from him. Abandoned by the entertainment industry, Sinatra was ruined and washed up, reduced to borrowing money from Gardner.
Awarded for Eternity
Sinatra’s career was revitalized in 1953. When he saw the script for the World War II drama From Here to Eternity, he became enchanted by the character of the Italian soldier Angelo Maggio, for whose part he immediately auditioned. Accepting less than a tenth of his usual fee, Sinatra put his heart into the film, earning an Academy Award for Best Supporting Actor.
From Columbia to Capitol
That same year, Sinatra left Columbia for Capitol. Over the next few years, Sinatra recorded the Grammy Hall of Fame albums In the Wee Small Hours (1955), Songs for Swinging Lovers (1955), and For Only the Lonely (1958). Come Dance with Me (1959) won the Grammy for Album of the Year.
In 1960, Sinatra started Reprise Records. The first single, The Second Time Around, won Grammy’s Record of the Year. September of My Years (1965) was named Album of the Year (also named to the Grammy Hall of Fame). That same award went to Sinatra’s album for his TV special A Man and His Music (1966). Strangers in the Night, his first chart-topper in 11 years, won Grammys in 1966 for Record of the Year and best vocal performance.
The Rat Pack and Other Friends
Throughout the ‘60s, “Ol’ Blue Eyes” was constant tabloid fodder. He threw support behind John F. Kennedy’s run for the Presidency in 1960, but Sinatra’s well-known mob ties became politically embarrassing for Kennedy once he became President.
No longer with Ava Gardner, Sinatra was romantically linked to actress Lauren Bacall and dancer Juliet Prowse, but married neither, instead tying the knot with 21-year-old actress Mia Farrow in 1966, a highly controversial move for the 51-year-old Sinatra.
He performed and hung out with Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop (aka “The Rat Pack”), a group known for their unique slang and “swinging” image. Sinatra maintained his tough reputation by threatening club owners and musicians whom he didn’t like, engaging in occasional drunken outbursts. He was often seen with mob figures such as Sam Giancana, a close friend.
Sinatra retired in 1971 to spend more time with his family. In 1972, he switched from bona fide liberal to right-wing conservative after being brought before the House Crime Committee as part of their investigation of the mafia.
By 1973 “The Chairman of the Board” returned with a new album and TV special. In 1976 he married yet again, this time to Barbara Marx, the widow of the Marx Brothers’ Zeppo Marx.
He didn’t release an album of new material again until 1980’s Trilogy: Past, Present, Future. which featured Theme from ‘New York, New York’, the title song from the 1977 movie. He recorded very little the rest of the decade, focusing more on live appearances.
In 1993, Capitol Records resigned Sinatra and he released Duets, a collection of old favorites with various singers ranging from Tony Bennett to U2’s Bono. With sales over three million, it became his biggest seller, and was followed in 1994 by Duets II, which won the 1995 Grammy Award for Traditional Pop Performance. Sinatra finally retired from performing in 1995. He died of a heart attack three years later at 82.