After playing drums in his high school band, Vallée played clarinet and saxophone in various bands around New England as a teenager. From 1924 through 1925, he played with the Savoy Havana Band at the Savoy Hotel in London, where his fellow band-members discouraged his attempts to become a vocalist. He then returned to the United States to obtain a degree in philosophy from Yale, where he played in the Yale Collegians with future New Yorker cartoonist Peter Arno.
After graduation, he formed his own band, "Rudy Vallée and the Connecticut Yankees", having named himself after influential saxophonist Rudy Wiedoeft. With this band, which featured two violins, two saxophones, a piano, a banjo and drums, he started singing (supposedly reluctantly at first). He had a rather thin, wavering tenor voice and seemed more at home singing sweet ballads than jazz numbers. However, his singing, together with his suave manner and boyish good looks, attracted great attention, especially from young women. Vallée was given a recording contract and in 1928, he started performing on the radio.
Vallée became the most prominent and, arguably, the first of a new style of popular singer, the crooner. Previously, popular singers needed strong projecting voices to fill theaters in the days before the electric microphone. Crooners had soft voices that were well suited to the intimacy of the new medium of the radio. Vallée's trombone-like vocal phrasing on "Deep Night" would inspire later crooners such as Bing Crosby, Frank Sinatra, and Perry Como to model their voices on jazz instruments.
On the Air 1933
Don't Play With Fire Test Pressing
Deep Night 1929
My Time Is Your Time 1929
Confessin' (That I Love You) 1930
Makin' Whoopee 1929
By the Sycamore Tree Hit of the Week Record
Love Is The Sweetest Thing 1933