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During the Great Depression, Dolly provided money to her son for outings with friends and to buy expensive clothes, resulting in neighbors describing him as the "best-dressed kid in the neighborhood"."They'd fought through his childhood and continued to do so until her dying day.

Sinatra released several critically lauded albums, including In the Wee Small Hours (1955), Songs for Swingin' Lovers!

(1956), Come Fly with Me (1958), Only the Lonely (1958) and Nice 'n' Easy (1960).

His pianist and close friend Hank Sanicola persuaded him to stay with the group, Dorsey recalled: "You could almost feel the excitement coming up out of the crowds when the kid stood up to sing. Dorsey was a major influence on Sinatra and became a father figure.

other authors state that they were friends and even roommates when the band was on the road, but professional jealousy surfaced as both men wanted to be considered the star of Dorsey's band.

Sinatra left Capitol in 1960 to start his own record label, Reprise Records, and released a string of successful albums.

In 1965, he recorded the retrospective September of My Years, starred in the Emmy-winning television special Frank Sinatra: A Man and His Music, and released the tracks "Strangers in the Night" and "My Way".

Sinatra would later receive the Golden Globe Cecil B. On television, The Frank Sinatra Show began on ABC in 1950, and he continued to make appearances on television throughout the 1950s and 1960s. Despite his political connections, the FBI investigated Sinatra and his alleged relationship with the Mafia.