In 1923, Crosby was invited to join a new band composed of high school students a few years younger than himself. Al Rinker, Miles Rinker, James Heaton, Claire Pritchard and Robert Pritchard, along with drummer Crosby, formed the Musicaladers,
 who performed at dances both for high school students and club-goers. The group performed on Spokane radio station
KHQ, but disbanded after two years.
 Crosby and Al Rinker then obtained work at the Clemmer Theatre in Spokane (now known as the
Bing Crosby Theater). Crosby was initially a member of a vocal trio called 'The Three Harmony Aces' with Al Rinker accompanying on piano from the pit, to entertain between the films. Bing and Al continued at the Clemmer Theatre for several months often with three other men – Wee Georgie Crittenden, Frank McBride and Lloyd Grinnell – and they were billed as 'The Clemmer Trio' or 'The Clemmer Entertainers' depending who performed.
In October 1925, Crosby and his partner
Al Rinker, brother of singer
Mildred Bailey, decided to seek fame in California. They traveled to Los Angeles where they met up with Mildred Bailey. She introduced them to her show business contacts, and the Fanchon and Marco Time Agency hired them for thirteen weeks for a revue called The Syncopation Idea, starting at the Boulevard Theater in Los Angeles and then on the Loew's circuit. They each earned $75 a week. Bing and Al Rinker began as a minor part of The Syncopation Idea and it was there that they started to develop as entertainers. They had a lively and individual style and were particularly popular with college students. After The Syncopation Idea closed, Bing and Al worked in the Will Morrissey Music Hall Revue. They further honed their skills with Morrissey, and blossomed when they subsequently had the chance to present their own independent act, and were quickly spotted by the
Paul Whiteman organization. At that time, it was felt that Whiteman needed something different and entertaining to break up his musical selections, and Crosby and Rinker filled this requirement. After less than a year in full-time show business, they had become part of one of the biggest names in the entertainment world.
 Hired for $150 a week in 1926, they debuted with Whiteman on December 6 at the
Tivoli Theatre in Chicago. Their first recording, in October 1926, 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, Crosby often credited Mildred Bailey for getting him his first important job in the entertainment business.
The Rhythm Boys
Initial successes with Whiteman were followed by disaster when they reached New York and Whiteman considered letting them go. Bing may have been retained as Whiteman was already using him as a solo performer on record, but the prospects for Rinker were bleak. However, the addition of pianist and aspiring songwriter
Harry Barris made the difference and "
The Rhythm Boys" were born. The additional voice meant the boys could be heard more easily in the large New York theaters and eventually became a success. A year touring with Whiteman performing and recording with musicians
Eddie Lang and
Hoagy Carmichael, provided valuable experience and began touring. Crosby then matured considerably as a performer and was in constant demand as a solo artist.
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". In 1929,
the Rhythm Boys appeared in the film
The King of Jazz with Whiteman but Bing's growing dissatisfaction with Whiteman led to
the Rhythm Boys leaving his organization. They joined the
Gus Arnheim Orchestra performing nightly in The
Coconut Grove of the Ambassador Hotel. Singing with the Arnheim Orchestra, Bing's solos began to steal the show, while the Rhythm Boys act gradually became redundant. Harry Barris wrote several of Crosby's subsequent hits including "At Your Command", "
I Surrender Dear", and "
Wrap Your Troubles In Dreams". In the early months of 1931, a solo recording contract came Bing's way,
Mack Sennett signed him to make film shorts and a break with the Rhythm Boys became almost inevitable. Bing had married Dixie Lee in September 1930 and after a threatened divorce in March 1931, he started to apply himself seriously to his career. His gramophone records in 1931 broke new ground as his powerful and emotional singing started to change the face of popular music forever.
Their low salaries at the Cocoanut Grove of the Ambassador Hotel had led the Rhythm Boys to walk out, causing union problems for Bing. Bing's brother, Everett, interested
Bill Paley of CBS in his brother and Paley beckoned Bing to come to New York. A settlement was reached with the Ambassador Hotel and Bing made his first solo national radio broadcast in September 1931 and then went on to star at the New York Paramount Theatre.
Success as a solo singer
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.
His first commercial sponsor on radio was
Cremo Cigars and increasingly his fame spread nationwide. After a long run in New York, Bing went back to Hollywood to film
The Big Broadcast and his personal appearances, his records, and his radio work substantially increased his impact. The success of his first full-length film brought him a contract with Paramount and he began a regular pattern of making three films a year. On radio, he fronted his own show for
Woodbury Soap for two seasons and gradually his live appearances dwindled. His records produced hit after hit at a time when record sales generally were in decline because of the Depression. Critically acclaimed audio engineer
Steve Hoffman once stated: "By the way, Bing actually saved the record business in 1934 when he agreed to support Decca founder Jack Kapp's crazy idea of lowering the price of singles from a dollar to 35 cents and getting a royalty for records sold instead of a flat fee. Bing's name and his artistry saved the recording industry. All the other artists signed to Decca after Bing did. Without him, Jack Kapp wouldn't have had a chance in hell of making Decca work and the Great Depression would have wiped out phonograph records for good."
 His social life was hectic, his first son
Gary was born in 1933 with twin boys following in 1934. By 1936, he'd replaced his former boss,
Paul Whiteman, as host of the prestigious NBC radio program
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.
Also in 1936, Crosby exercised an option from Paramount to make a film out-of-house. Quickly signed to a one-picture agreement with Columbia, Crosby dreamt of having his icon and friend
Louis Armstrong, an African-American, who largely influenced his singing style, in a screen adaptation of The Peacock Feather called
Pennies from Heaven. Crosby talked to
Harry Cohn about the matter, but he disagreed saying: "... no reason to entail the expense of flying him in and having no desire to negotiate with Armstrong's crude, mob-linked but devoted manager,
Joe Glaser." Bing threatened to walk out on the film and refused to discuss it with Cohn. Armstrong's musical scenes, along with some comical dialogue as well, heightened his career. Bing also had it that Armstrong made high billing alongside his white co-stars, one of the first times ever for a black performer in a wide-audience film. He starred as himself in many more films to come and had a large appreciation for Bing's unracist views, often thanking him in his later years.
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 "
Second World War, 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
The June 18, 1945, issue of
Life magazine stated: "America's number one star, Bing Crosby, has won more fans, made more money than any entertainer in history. Today he is a kind of national institution." They also state: "In all, 60,000,000 Crosby disks have been marketed since he made his first record in 1931. His biggest best seller is White Christmas, 2,000,000 impressions of which have been sold in the U.S. and 250,000 in Great Britain." They go on to say: "Nine out of ten singers and bandleaders listen to Crosby's broadcasts each Thursday night and follow his lead. The day after he sings a song over the air – any song – some 50,000 copies of it are sold throughout the U.S. Time and again Crosby has taken some new or unknown ballad, has given it what is known in trade circles as the "big goose" and made it a hit single-handed and overnight." and "Precisely what the future holds for Crosby neither his family nor his friends can conjecture. He has achieved greater popularity, made more money, attracted vaster audiences than any other entertainer in history. And his star is still in the ascendant. His contract with Decca runs until 1955. His contract with Paramount runs until 1954. Records which he made ten years ago are selling better than ever before. The nation's appetite for Crosby's voice and personality appears insatiable. To soldiers overseas and to foreigners he has become a kind of symbol of America, of the amiable, humorous citizen of a free land. Crosby, however, seldom bothers to contemplate his future. For one thing, he enjoys hearing himself sing, and if ever a day should dawn when the public wearies of him, he will complacently go right on singing – to himself."
The biggest hit song of Crosby's career was his recording of
Irving Berlin's "
White Christmas", which he introduced on a Christmas Day radio broadcast in 1941. (A copy of the recording from the radio program is owned by the estate of Bing Crosby and was loaned to
CBS Sunday Morning for their December 25, 2011, program.) The song then appeared in his 1942 movie
Holiday Inn. His record hit the charts on October 3, 1942, and rose to No. 1 on October 31, where it stayed for 11 weeks. A holiday perennial, the song was repeatedly re-released by Decca, charting another 16 times. It topped the charts again in 1945 and for a third time in January 1947. The song remains the bestselling single of all time.
 According to
Guinness World Records, his recording of "White Christmas" has sold over 100 million copies around the world, with at least 50 million sales as singles.
 His recording was so popular that he was obliged to re-record it in 1947 using the same musicians and backup singers; the original 1942 master had become damaged due to its frequent use in pressing additional singles. Though the two versions are similar, the 1947 recording is more familiar today. After his death in 1977, the song was re-released and reached the No. 5 position in the UK Singles Chart in December 1977.
 Crosby was dismissive of his role in the song's success, saying "a jackdaw with a cleft palate could have sung it successfully."
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Crosby with Bob Hope in Road to Bali
Crosby starred with
Bob Hope and
Dorothy Lamour in seven
Road to musical comedies between 1940 and 1962, cementing Crosby and Hope as an on-and-off duo, despite never officially declaring themselves a "team" in the sense that
Laurel and Hardy or
Dean Martin and Jerry Lewis were teams. The series consists of
Road to Singapore (1940),
Road to Zanzibar (1941),
Road to Morocco (1942),
Road to Utopia (1946),
Road to Rio (1947),
Road to Bali (1952), and
The Road to Hong Kong (1962). When they appeared solo, Crosby and Hope frequently made note of the other in a comically insulting fashion. They performed together many times on stage, radio, film, and television.
Crosby in Road to Singapore
In the 1949 Disney animated film
The Adventures of Ichabod and Mr. Toad, Crosby provided the narration and song vocals for The Legend of Sleepy Hollow segment, and again in the October 1977 animated Disney film
The Many Adventures of Ichabod
and Winnie the Pooh.
In 1960, he starred in
High Time, a collegiate comedy with
Fabian Forte and
Tuesday Weld that predicted the emerging gap between him and the new young generation of musicians and actors who had begun their careers after WWII. The following year, Crosby and Hope reunited for one more Road movie,
The Road to Hong Kong, which teamed them up with the much younger
Joan Collins and
Peter Sellers. Collins was used in place of their longtime partner Dorothy Lamour, whom Crosby felt was getting too old for the role, though Hope refused to do the movie without her, and she instead made a cameo appearance.
 Shortly before his death in 1977, he had planned another Road film in which he, Hope, and Lamour search for the Fountain of Youth.
He won an
Academy Award for Best Actor for
Going My Way in 1944 and was nominated for the 1945 sequel,
The Bells of St. Mary's. He received critical acclaim for his performance as an alcoholic entertainer in
The Country Girl and received his third Academy Award nomination.
In 1958, Crosby and his brother helped produce a
pornographic film for the
CIA. An actor was fitted with a
latex face mask of the
President of Indonesia
Sukarno and filmed performing sex acts on a blonde woman, which was used by the CIA to imply that Sukarno had been seduced by an agent of the
Crosby and his family in a Christmas special, 1974
The Fireside Theater (1950) was his first television production. The series of 26-minute shows was filmed at
Hal Roach Studios rather than performed live on the air. The "telefilms" were syndicated to individual television stations. He was a frequent guest on the musical variety shows of the 1950s and 1960s. He was associated with ABC's
The Hollywood Palace. He was the show's first and most frequent guest host and appeared annually on its Christmas edition with his wife Kathryn and his younger children. In the early 1970s, he made two late appearances on the
Flip Wilson Show, singing duets with the comedian. His last TV appearance was a Christmas special filmed in London in September 1977 and aired weeks after his death.
 It was on this special that he recorded a duet of "
The Little Drummer Boy" and "Peace on Earth" with rock star
David Bowie. Their duet was released in 1982 as a single 45-rpm record and reached No. 3 in the UK singles charts.
 It has since become a staple of holiday radio and the final popular hit of Crosby's career. At the end of the 20th century, TV Guide listed the Crosby-Bowie duet as one of the 25 most memorable musical moments of 20th-century television.
Bing Crosby Productions, affiliated with
Desilu Studios and later
CBS Television Studios, produced a number of television series, including Crosby's own unsuccessful ABC sitcom
The Bing Crosby Show in the 1964–1965 season (with co-stars
Beverly Garland and
Frank McHugh). The company produced two ABC medical dramas,
Ben Casey (1961–1966) and
Breaking Point (1963–1964), the popular
Hogan's Heroes (1965–1971) military comedy on CBS, as well as the lesser-known show
Slattery's People (1964–1965).