In 1923, Bing Crosby was invited to join a new band composed of high school students much younger than himself. Al Rinker, Miles Rinker, James Heaton, Claire Pritchard and Robert Pritchard, along with drummer Bing Crosby, formed the Musicaladers, who performed at dances both for high school students and club-goers. The group disbanded after two years.
By 1925, Crosby had formed a vocal duo with partner Al Rinker, brother of singer Mildred Bailey. Mildred introduced Al and Bing to Paul Whiteman, who was at that time America's most famous bandleader. Hired for $150 a week, they made their debut on December 6, 1926 at the Tivoli Theatre (Chicago). Their first recording was "I've Got The Girl," with Don Clark's Orchestra, but the Columbia-issued record did them no vocal favors, as it was inadvertently recorded at a speed slower than it should have been, which increased the singers' pitch when played at 78 rpm. Throughout his career, Bing Crosby often credited Mildred Bailey for getting him his first important job in the entertainment business.
Even as the Crosby and Rinker duo was increasing in popularity, Whiteman added a third member to the group. The threesome, now including pianist and aspiring songwriter Harry Barris, were dubbed "The Rhythm Boys". They joined the Whiteman touring act, performing and recording with musicians Bix Beiderbecke, Jack Teagarden, Tommy Dorsey, Jimmy Dorsey, and Eddie Lang and Hoagy Carmichael, and appeared together in a Whiteman movie.
Crosby soon became the star attraction of the Rhythm Boys, and in 1928 he had his first number one hit with the Whiteman orchestra, a jazz-influenced rendition of "Ol' Man River". However, Crosby's reported taste for alcohol and his growing dissatisfaction with Whiteman led to his quitting the Rhythm Boys to join the Gus Arnheim Orchestra. During his time with Arnheim, the other two Rhythm Boys were increasingly pushed to the background as the emphasis was on Crosby. Harry Barris wrote several of Crosby's subsequent hits including "At Your Command," "I Surrender Dear", and "Wrap Your Troubles In Dreams". But the members of the band had a falling out and split, setting the stage for Crosby's solo career.
On September 2, 1931, Crosby made his solo radio debut. Before the end of the year, he signed with both Brunswick Records and CBS Radio. Doing a weekly 15-minute radio broadcast, Crosby quickly became a huge hit. His songs "Out of Nowhere", "Just One More Chance", "At Your Command" and "I Found a Million Dollar Baby (in a Five and Ten Cent Store)" were all among the best selling songs of 1931.
As the 1930s unfolded, Crosby became the leading singer in America. Ten of the top 50 songs for 1931 featured Crosby, either solo or with others. A so-called "Battle of the Baritones" with singing star Russ Columbo proved short-lived, replaced with the slogan "Bing Was King." Crosby played the lead in a series of sound era musical comedy short films for Mack Sennett, signed with Paramount and starred in his first full-length feature, 1932's The Big Broadcast, the first of 55 films in which he received top billing. He would appear in 79 pictures, and signed a long-term deal with Jack Kapp's new record company Decca in late 1934,
Around this time, Crosby co-starred on radio with The Carl Fenton Orchestra on a popular CBS radio show. By 1936, he'd replaced his former boss, Paul Whiteman, as the host of NBC's Kraft Music Hall, the weekly radio program where he remained for the next ten years. "Where the Blue of the Night (Meets the Gold of the Day)", which showcased one of his then-trademark whistling interludes, became his theme song and signature tune.
Crosby's much-imitated style helped take popular singing beyond the kind of "belting" associated with boisterous performers like Al Jolson and Billy Murray, who had been obliged to reach the back seats in New York theaters without the aid of the microphone. As Henry Pleasants noted in The Great American Popular Singers, something new had entered American music, a style that might be called "singing in American" with conversational ease. This new sound led to the popular epithet "crooner".
Crosby in Road to Singapore (1940)
Crosby made numerous live appearances before American troops fighting in the European Theater. He also learned how to pronounce German from written scripts and would read propaganda broadcasts intended for the German forces. The nickname "Der Bingle" was common among Crosby's German listeners and came to be used by his English-speaking fans. In a poll of U.S. troops at the close of World War II, Crosby topped the list as the person who had done the most for G.I. morale, ahead of President Franklin Delano Roosevelt, General Dwight Eisenhower, and Bob Hope.