Francis Albert Sinatra [was born] in Hoboken, New Jersey. Although his mother had hoped that he would be the first person in the family to attend college and was disappointed that he did not finish high school, she encouraged his ambition to be a singer. His father, on the other hand, was opposed and insisted that he should find a job. The young Sinatra worked briefly as a truck driver for a newspaper, a riveter in a Hoboken shipyard, and a fruit hauler. By 1932, he had decided that he wanted to be a professional singer.
FROM http://www.anb.org/view/10.1093/anb/9780198606697.001.0001/anb-9780198606697-e-1803570

His break came in 1937, when he and three instrumentalists, billed as the Hoboken Four, won on the Major Bowes Original Amateur Hour. After some touring, the group disbanded. Harry James signed Sinatra to sing with his orchestra, and on July 13, 1939, two weeks after his debut as a big-band vocalist at the Hippodrome Theatre in Baltimore, Sinatra cut his first disc, “From the Bottom of My Heart,” with the orchestra.
FROM https://www.rollingstone.com/music/music-news/an-appreciation-of-frank-sinatra-1915-1998-59176/

James graciously freed Sinatra from his contract when the singer received a more lucrative offer from bandleader Tommy Dorsey in December 1939. By 1942 Sinatra’s fame had eclipsed that of Dorsey, and the singer yearned for a solo career.
FROM https://www.britannica.com/biography/Frank-Sinatra

Between 1943 and 1946, Sinatra’s solo career blossomed as the singer charted a slew of hit singles. Sinatra made his movie acting debut in 1943. In 1945, he won a special Academy Award for The House I Live In, a 10-minute short made to promote racial and religious tolerance on the home front. Sinatra’s popularity began to slide in the postwar years (but) in 1953, he made a triumphant comeback, winning a supporting actor Oscar for From Here to Eternity.
FROM https://www.biography.com/people/frank-sinatra-9484810

In the mid-’70s Sinatra’s career slowed down, but in mid-1980, after a five-year recording hiatus, he released Trilogy which included a version of “Theme From New York, New York” that the city fervently adopted. In 1985, he was accorded the Presidential Medal of Freedom, the nation’s highest civilian award. Frank Sinatra died of a heart attack on May 14, 1998, in L.A.
FROM https://www.rollingstone.com/music/music-news/an-appreciation-of-frank-sinatra-1915-1998-59176/