He became a successful in the early 1940s. Sinatra had several albums with Capitol Records (In the Wee Small Hours in 1955, Songs for Swingin' Lovers in 1956, Come Fly with Me in 1957) until he found his own record label, Reprise Records (September Of My Years in 1965). He also was a founding member of the Rat Pack.
Sinatra retired for the first time in 1971. In 1973 he already had a comeback and recorded several albums, including the hit "(Theme From) New York, New York" and Trilogy: Past Present Future in 1980.
In February 1995 Sinatra sang before a live audience for the very last time. His last song was "The Best is Yet to Come".