Bing Crosby Trivia
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49 free Bing Crosby trivia questions with answers — music quiz, new questions added Aug 2026.
Bing Crosby trivia for classic-Hollywood fans, Christmas-music devotees and anyone who has ever hummed along to White Christmas without knowing much about the man singing it. This quiz starts in Tacoma and Spokane, with the boy nicknamed after a newspaper comic strip who studied at Gonzaga, drummed in a local band and joined Paul Whiteman's orchestra as one of the Rhythm Boys. From there it covers the crooner who changed popular singing, the radio star of the Kraft Music Hall, the Oscar for Going My Way and the priest he played twice, the seven Road pictures with Bob Hope and Dorothy Lamour, High Society and The Country Girl, and the biggest-selling single of all time. It also visits the businessman: the 50,000-dollar bet on Ampex tape recorders that changed broadcasting, the Minute Maid fortune, the Pittsburgh Pirates share, the Del Mar racetrack, the Pebble Beach 'Clambake', and the final years, from the David Bowie duet to his death on a Madrid golf course. Questions range from easy to expert, and every answer was checked against a reference page and carries its source. If you enjoy this quiz, try our Bob Hope, Frank Sinatra and Christmas songs quizzes next.
30 of 49 questions with answers and explanations. Play the quiz
Q 01In which Washington State city was Bing Crosby born in 1903?
Tacoma
Bing Crosby was born in Tacoma on 3 May 1903, at 1112 North J Street; the family moved east to Spokane in 1906, where he grew up.
Q 02What was Bing Crosby's real first name?
Harry
He was Harry Lillis Crosby Jr., born in 1903 to bookkeeper Harry Lowe Crosby and his Irish-American wife Catherine Harrigan.
Q 03Where did the nickname 'Bing' come from?
A newspaper comic feature called The Bingville Bugle
A neighbour, Valentine Hobart, dubbed the boy 'Bingo from Bingville' around 1910.
Q 04Which Spokane college did Crosby attend for three years without graduating?
Gonzaga
Gonzaga University in Spokane enrolled Crosby from 1920; he left after three years without a degree, and the campus now keeps his boyhood home as a museum, his Oscar included.
Q 05Which instrument did Crosby play in the Musicaladers, his first band in Spokane?
Drums
Crosby played drums, bought by mail order, in the Musicaladers, the Spokane band he formed with Al Rinker around 1923; the two left for California in 1925.
Q 06Crosby's first big break came when he and Al Rinker were hired in 1926 by which bandleader?
Paul Whiteman
Paul Whiteman signed Crosby and Rinker in 1926 at 150 dollars a week; they debuted with his orchestra at Chicago's Tivoli Theatre that December.
Q 07Crosby, Al Rinker and Harry Barris performed as which vocal trio?
The Rhythm Boys
The Rhythm Boys formed in 1927 when pianist-songwriter Barris joined Crosby and Rinker; the trio appeared in the 1930 film King of Jazz.
Q 08Crosby's first number one hit, in 1928, was a jazz-influenced version of which song?
Ol' Man River
Jerome Kern's 'Ol' Man River', from Show Boat, was Crosby's first number one in 1928, recorded as a band vocalist alongside Bix Beiderbecke and the Dorsey brothers.
Q 09Which record company did Crosby sign with in late 1934, backing its 35-cent singles?
Decca
Decca, founded by Jack Kapp in 1934, signed Crosby that year and sold his records at 35 cents; Kapp also steered him from jazzy mannerisms toward a cleaner vocal style.
Q 10Which weekly NBC radio show did Crosby host from 1936 for a decade?
Kraft Music Hall
Crosby hosted NBC's Kraft Music Hall from January 1936 until 1946, opening each week with his theme 'Where the Blue of the Night (Meets the Gold of the Day)'.
Q 11Which trumpeter got equal billing at Crosby's insistence in Pennies from Heaven?
Louis Armstrong
Louis Armstrong received featured billing on Pennies from Heaven (1936) after Crosby insisted on it, rare then for a Black performer; the two later sang 'Now You Has Jazz' together in High Society.
Q 12Crosby's intimate singing style, made possible by the microphone, earned which popular label?
Crooner
Crooner became the label for Crosby's intimate, microphone-based style, which replaced the shouting projection earlier stars needed to reach the back rows unamplified.
Q 13On what date did Crosby first perform 'White Christmas' on his radio show?
25 December 1941
Q 21Which Best Original Song winner did Crosby sing with a boys' choir as Father O'Malley?
Swinging on a Star
'Swinging on a Star', by Jimmy Van Heusen and Johnny Burke, won the 1944 Best Original Song Oscar; Crosby introduced four winning songs in all, beginning with 'Sweet Leilani' in 1937.
Q 22The first of the Crosby-Hope buddy pictures, in 1940, took them on the road to where?
Singapore
Road to Singapore (1940) launched the series, with Crosby and Hope as playboys fleeing to the South Seas; another film, Road to the Fountain of Youth, was in planning when Crosby died in 1977.
Q 23Who was the female lead in all but the last of the Road films?
Dorothy Lamour
Crosby first sang 'White Christmas' on his NBC radio show on 25 December 1941, eighteen days after Pearl Harbor; he recorded it the following May in about 18 minutes.
Q 14Who wrote 'White Christmas'?
Irving Berlin
Berlin called it not just the best song he ever wrote but 'the best song anybody ever wrote'.
Q 15Crosby's 'White Christmas', the best-selling physical single, has sold over how many copies?
50 million
Crosby's 'White Christmas' has estimated sales of more than 50 million copies, the most of any physical single; the familiar version is a 1947 re-recording made after the 1942 master wore out.
Q 16What self-deprecating remark did Crosby make about his part in the success of 'White Christmas'?
'A jackdaw with a cleft palate could have sung it successfully'
Crosby downplayed his role, saying 'a jackdaw with a cleft palate could have sung it successfully'; the song stayed his signature for the rest of his life.
Q 17'White Christmas' was introduced in which 1942 film co-starring Fred Astaire?
Holiday Inn
The film's title later inspired the name of the Holiday Inn hotel chain.
Q 18For which 1944 film did Crosby win the Academy Award for Best Actor?
Going My Way
Going My Way (1944) won Crosby the Best Actor Oscar as Father Chuck O'Malley; the film was the year's top earner and also took Best Picture.
Q 19Crosby's Oscar nod for The Bells of St. Mary's made him the first actor nominated twice for what?
Playing the same character
Crosby's 1945 nomination for The Bells of St. Mary's was for playing the same character, Father O'Malley, as in his Oscar-winning film of the previous year; no actor had been nominated twice for one role before.
Q 20Who played the elderly priest Father Fitzgibbon opposite Crosby's Father O'Malley?
Barry Fitzgerald
Barry Fitzgerald played the old pastor Father Fitzgibbon and won Best Supporting Actor after being nominated as both lead and supporting actor for the one role, a quirk the Academy then outlawed.
Dorothy Lamour, the sarong girl, was the female lead in every Road picture except The Road to Hong Kong (1962), where she was reduced to a cameo after Crosby judged her too old.
Q 24Crosby earned his third Oscar nomination playing an alcoholic has-been actor in which 1954 film?
The Country Girl
The Country Girl (1954) cast Crosby as Frank Elgin, a washed-up alcoholic actor, his third Oscar nomination; Grace Kelly won Best Actress as his wife and William Holden co-starred.
Q 25High Society (1956), starring Crosby, Grace Kelly and Frank Sinatra, was a musical remake of which film?
The Philadelphia Story
High Society reworked The Philadelphia Story, the 1940 Katharine Hepburn comedy, with Cole Porter songs and the setting moved from Philadelphia's Main Line to Newport, Rhode Island.
Q 26In which five consecutive years was Crosby America's number one box-office attraction?
1944-1948
Crosby topped the Quigley exhibitors' poll of box-office stars every year from 1944 to 1948; in 1946 alone he starred in three of the year's five biggest hits.
Q 27Bing Crosby invested $50,000 in which company to build tape recorders after seeing a captured German machine?
Ampex
Crosby put 50,000 dollars into Ampex in 1947 after hearing a Magnetophon captured from Germany; its Model 200 let him pre-record his radio shows, and he gave Les Paul one.
Q 28Bing Crosby Enterprises gave the first demonstration of what technology in November 1951?
Videotape recording
Bing Crosby Enterprises showed videotape recording in Los Angeles on 11 November 1951, a machine by John Mullin and Wayne Johnson running quarter-inch audio tape at 360 inches per second; the images were 'blurred and indistinct'.
Q 29Crosby made a fortune as a principal stockholder in which juice company?
Minute Maid
Crosby was an early principal stockholder in Minute Maid, promoting its frozen orange juice concentrate on a daily radio show from 1948 and later in television commercials with his family.
Q 30Crosby owned a 25% share of which baseball team from 1946 until his death?
Pittsburgh Pirates
Crosby held a minority stake in the Pittsburgh Pirates from 1946 until he died; too nervous to watch Game 7 of the 1960 World Series, he listened by radio in Paris and had the telecast kinescoped.