Frank Sinatra decided to become a singer after hearing Bing Crosby on the radio. He began singing in small clubs in New Jersey and eventually attracted the attention of band-leader Harry James. After a brief stint with James, he joined the Tommy Dorsey Orchestra in 1940 where he rose to fame as a singer. His vast appeal was to the "bobby soxers," as teenage girls were called. (The complete span of his career with Dorsey was released in the 1994 box set The Song Is You.) It was as a featured singer with Dorsey that Sinatra made his earliest film appearances, such as the 1942 Eleanor Powell/Red Skelton comedy, Ship Ahoy in which the uncredited singer performed a couple of songs.
He later signed with Columbia Records as a solo artist with some success, particularly during the musicians' recording strikes. Vocalists were not part of the musician union and were allowed to record during the ban with a vocal backing.

In the beginning of Sinatra's career, it can be said that it anticipated virtually every phase of what, would be called "the youth movement." His sudden--and for many his alarming--appeal to teenagers became a topic of journalistic and even sociological comment.

Sinatra's singing career was in decline in the late 1940s and early 1950s, a period when novelty tunes became popular with audiences and during which Sinatra's ageing would cause some loss of appeal to new teen-age audiences but Sinatra would succeed in re-establishing his popularity and taking it far beyond what he had achieved in the 1940s.

Sinatra had begun appearing in movies in the early 1940s, but usually in musicals, often undistinguished ones. He also appeared on a weekly television show on CBS for two years from 1950-1952 (and would try again for one year on ABC from 1957-1958).
What could be called Sinatra's second career began as a dramatic actor when he played the scrappy Pte. Angelo Maggio in the Pearl Harbour drama From Here to Eternity (1953), for which he won an Academy Award for Best Supporting Actor. This role and performance became legendary at the time as the key comeback moment in Sinatra's career. Overnight, his career recovered.
The following year, Sinatra played a coldblooded assassin determined to kill the President in the thriller Suddenly (available freely online in the USA); critics found Sinatra's performance one of the most chilling portrayals of a psychopath ever committed to film. This was followed in 1955 by his portrayal of a heroin addict in 1955's The Man with the Golden Arm, for which he received an Academy Award Best Actor nomination. Soon after From Here to Eternity, Sinatra's singing career rebounded.

During the 1950s, he signed with Capitol Records, where he worked with many of the best arrangers of the time, such as Nelson Riddle, Gordon Jenkins, and Billy May, and with whom he made highly-regarded recordings. By the early 1960s, he was a big enough star to start his own record label: Reprise Records. His position with the label earned him the long-lasting nickname "The Chairman of the Board".

There seemed little in either his 1940s film career or his radio and television performances of the early 1950s to predict the dramatic success he would enjoy on screen in the 1950s and 1960s. However, the musical turnaround should not have been unexpected. At the very end of his Columbia recording career, in two performances in 1952 Sinatra had given advance warning of what would become the new sound he achieved in the 1950s at Capitol. In "The Birth of the Blues" it would be the sound of the new and "swinging" Sinatra: more masculine than the sometimes boyish Sinatra of the 1940s. In "I'm A Fool To Want You" he anticipated the darker, sound of the great "torch" albums of the 1950s. Neither performance was sufficient to prevent Columbia from declining to renew his contract, in what must surely rank as one of the great errors in the business history of American popular music.

In the 1950s and 1960s, he became the most popular attraction in Las Vegas. He was friends with many other entertainers, including Dean Martin, Sammy Davis, Jr, actor Peter Lawford, comedian Joey Bishop, and sometimes Shirley MacLaine. They formed the Rat Pack, a loose group of entertainers who were friends and socialized together.
Sinatra played a major role in the desegregation of Nevada hotels and casinos in the 1960s. He led his fellow members of the Rat Pack in refusing to patronize hotels and casinos that denied service to Sammy Davis Jr., a black man.
With the release of the film Ocean's Eleven (1960), the Rat Pack became the subject of great media attention, and this gave the Rat Pack, Sinatra in particular the leverage they needed to force hotels and casinos to end segregation.

Sinatra resumed his filming with the 1962 classic The Manchurian Candidate, in which he plays the troubled, resolute protagonist. In 1965's Von Ryan's Express, Sinatra added dimensionality to a World War II action role. Another film during this time was 1964's Robin and the Seven Hoods.

In the 1970s he recorded less frequently but continued to perform in Las Vegas and around the world. It was a period during which Sinatra sought to bring the great American songbook of the 1920s and 1930s to a wider audience than the ones in Las Vegas.
He continued singing into the 1990s, with his successful Duets albums on which he sang with other stars such as U2's Bono. He continued to perform live until February 1995, but the nearly 80-year-old singer often had to rely on teleprompters for his lyrics, to compensate for his failing memory.

Frank married the actress Ava Gardner on November 7, 1951, only ten days after his divorce from his first wife became final. They were separated on October 27, 1953 but were not divorced until 1957. She was considered to be his truest love, but that did not guarantee marital success and stability in Hollywood.
Sinatra asked actress Lauren Bacall, whom he had been seeing since shortly after her husband Humphrey Bogart died in 1957, to marry him, but reneged when word of their relationship became public.

On December 8, 1963, his son Frank Jnr. was kidnapped. Sinatra paid the kidnappers' $240,000 ransom demand and his son was released unharmed on December 10. Because the kidnappers demanded that Sinatra call them only from payphones, Sinatra carried a roll of dimes with him throughout the ordeal, and this became a lifetime habit. The kidnappers were subsequently apprehended and convicted. A movie called "Stealing Sinatra" has been shot about this kidnap.

Sinatra married actress Mia Farrow, 30 years his junior, in 1966. They were divorced two years later.
In 1976, Sinatra married Barbara Blakeley Marx (formerly married to Zeppo Marx), who converted to Catholicism to marry him. She remained his wife until his death.

He died aged 82 of a heart attack in Los Angeles, California, following a long battle with coronary heart disease, kidney disease, bladder cancer, and dementia. He had undergone surgery to remove part of his intestines in 1986, and had suffered a bad fall from the stage in 1994. His funeral was held on May 20, 1998 at the Church of the Good Shepherd in Beverly Hills and his last words were as told by his daughter Nancy: "I'm losing."
Sinatra was buried a few miles away from Palm Springs next to his parents in Desert Memorial Park in Cathedral City, a quiet, unassuming cemetery near his famous compound in Rancho Mirage, California, which is on the tree-lined thoroughfare that bears his name.