The epitome of the transition from the bandleader to the singer was
one of the creative forces of jazz phrasing
("the voice") and the quintessential Italian baritone.
He took Bing Crosby's romantic crooning to new evocative (and swooning) heights.
He debuted in the big bands of Harry James, in 1939,
and, between 1940 and 1942, Tommy Dorsey (of whom Sinatra
basically emulated vocally the expansive trombone style).
As he launched his solo career, he collected a repertory of ballads
that served him well throughout his career, notably
Johnny Mercer's Dream (1945),
Victor Young's Stella by Starlight (1947),
Ken Lane's Everybody Loves Somebody (1948),
Frank Loesser's Luck Be A Lady Tonight (1950),
Johnny Richards' Young At Heart (1954),
Cole Porter's I've Got You Under My Skin (1956),
Harry Warren's You're Getting to be A Habit With Me (1956),
Stephan Weiss' Put Your Dreams Away (1957),
Johnny Mercer's Blues In The Night (1958),
Vernon Duke's April In Paris (1959),
Bert Kaempfert's Strangers In The Night (1966),
Billy Byers' The Lady is a Tramp.
He also sang with the big bands of Count Basie and Duke Ellington.
His albums, starting with
the chamber-jazz arrangements of Swing Easy (1954),
were among the most refined of the 1950s.
In The Wee Small Hours (1955), arranged by Nelson Riddle, is a contender for the title of first concept album.
Songs For Swinging Lovers (1956), again arranged by Riddle, fused swing's big band and string orchestra.
Come Fly With Me (1958) was arranged by Billy May.
In 1960 Sinatra founded Reprise Records and his albums (arranged by veterans
of the swing era) returned to a jazzier sound.
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