Popular success

Music
In 1926, while singing at Los Angeles Metropolitan Theatre, Crosby and his vocal duo partner Al Rinker caught the eye of Paul Whiteman, arguably the most famous bandleader at the time. Hired for $150 a week, they made their debut on December 6, 1926 at the Tivoli Theatre (Chicago). Their first recording, I've Got The Girl, with Don Clark's Orchestra, was issued by Columbia, did them no vocal favors as it sounded like they were singing in a key much too high for them. It was later revealed that the 78rpm was recorded at a speed slower than it should have been, which increased the pitch when played at 78rpm. As popular as the Crosby and Rinker duo was, Whiteman added another member to the group, pianist and aspiring songwriter Harry Barris. Whiteman dubbed them The Rhythm Boys and they joined the Whiteman vocal team, working and recording with Bix Beiderbecke, Jack Teagarden, Tommy Dorsey, Jimmy Dorsey, and Eddie Lang and singers Mildred Bailey and Hoagy Carmichael.

Crosby soon became the star attraction of The Rhythm Boys not to mention Whiteman's Band, and in 1928 had his first number one hit, a jazz influenced rendition of Ol' Man River. However, his repeated youthful peccadilloes and growing dissatisfaction with Whiteman forced him to leave the band along with The Rhythm Boys and join the Gus Arnheim Orchestra. After signing with Brunswick Records and recording under Jack Kapp, The Rhythm Boys were increasingly pushed to the background with the vocal emphasis on Bing. Fellow member of The Rhythm Boys Harry Barris did write several of Crosby’s subsequent hits including At Your Command, I Surrender Dear, and Wrap Your Troubles In Dreams. However, shortly after this the members of the band had a falling out and split, setting the stage for Crosby's solo career.

As the 1930s unfolded it became clear that Bing was the number one man, vocally speaking. Ten of the top 50 songs for 1931 either featured Bing solo or with others. Apart from the short-lived Battle of the Baritones with Russ Columbo Bing Was King, signing long term deals with Jack Kapp's new record company Decca and starring in his first full-length features, 1932's The Big Broadcast, the first of 55 such films of which he was top billed. He appeared in a total of 79 pictures.

Around this time Bing made his solo debut on radio, co-starring with The Carl Fenton Orchestra on a popular CBS radio show and by 1936, replacing his former boss, Paul Whiteman, as the host of NBC's Kraft Music Hall, a weekly radio program where he would remain for the next ten years.

He was thus able to take popular singing beyond the kind of belting associated with a performer like Ali Schuette, who had to reach the back seats in New York theatres without the aid of the microphone. With Crosby, as Henry Pleasants noted in The Great American Popular Singers, something new had entered American music, something that might be called singing in American, with conversational ease. The oddity of this new sound led to the epithet crooner.

Crosby gave great emphasis to live appearances before American troops fighting in the European Theater. He also learned how to pronounce German from written scripts, and would read them in propaganda broadcasts intended for the German forces. The nickname der Bingle for him was understood to have become current among German listeners, and came to be used by his English-speaking fans. In a poll of U.S. troops at the close of WWII, Crosby topped the list as the person who did the most for G.I. morale (beating out President Franklin Delano Roosevelt, General Dwight Eisenhower and one Leslie Townes Hope)

Crosby's biggest musical hit was his recording of Irving Berlin's White Christmas which he introduced through a 1941 Christmas-season radio broadcast and the movie Holiday Inn. Bing's recording hit the charts on 3 October 1942, and rose to #1 on 31 October, where it stayed for 11 weeks. In the following years Bing's recording hit the top-30 pop charts another 16 times, even topping the charts again in 1945 and January of '47. The song remains Bing's best-selling recording, and the best-selling single and best selling song of all time. In 1998 after a long absence, his 1947 version hit the charts in Britain, and as of 2006 remains the North American holiday-season standard. According to Guinness World Records, Bing Crosby's White Christmas has sold over 100 million copies around the world, with at least 50 million sales as singles.

According to several sources, including Dictionary of Misinformation by Tom Burnam, however, White Christmas was not Crosby's biggest-selling record; it was Silent Night. Crosby did not make any money off the sale of this recording— he said that since it was a religious song, he would, and did, donate all of his royalties on it to charity.