Bing Crosby Trivia
0Loading crowd target
0Loading crowd target
7correct to beat the crowd
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 01Bing Crosby grew up in Spokane, but in which Washington city was he born?
Tacoma
Tacoma was home for just three years: his father built the family's house there, then in 1906 moved everyone across the state to Spokane.
Q 02What was Bing Crosby's real first name?
Harry
Harry Lillis Crosby shared his first name with his father, but he barely used it: by about the age of seven a neighbour's nickname had replaced it for good.
Q 03The Bingville Bugle, usually credited as the source of Crosby's nickname, was what kind of boyhood favourite?
A newspaper comic feature
A newspaper comic feature: it ran in his local paper, and around 1910 a neighbour took to calling the boy 'Bingo from Bingville', which was soon cut down to Bing.
Q 04Which Washington college did Crosby leave without a degree to chase a career in music?
Gonzaga
Gonzaga University displays his Oscar on campus; in 1972 a prankster swapped the statuette for a three-inch Mickey Mouse figurine, and it turned up unharmed a week later.
Q 05Which instrument did Crosby play in the Musicaladers, his Spokane dance band of the 1920s?
Drums
Drums were his job in the Musicaladers, the dance band led by pianist Al Rinker; when it folded after two years, the pair left Spokane for Los Angeles to try show business.
Q 06Which bandleader, billed as the 'King of Jazz', hired Crosby and Al Rinker in 1926?
Paul Whiteman
Paul Whiteman put the two Spokane newcomers in front of America's best-known orchestra; Rinker's sister, the singer Mildred Bailey, had got them their first auditions in Los Angeles.
Q 07Crosby, Al Rinker and Harry Barris performed as which vocal trio?
The Rhythm Boys
The Rhythm Boys sang in the 1930 film King of Jazz, but Crosby lost his solo number in it: he was jailed after a drink-driving crash and the song went to John Boles.
Q 08In 1928 Crosby sang on a fast, jazzy hit version of which song from the new musical Show Boat?
Ol' Man River
Ol' Man River was written as a slow lament for a bass voice; the dance-band record Crosby sang on took it far faster than its writers intended, with Bix Beiderbecke on cornet.
Q 09Which record company did Crosby sign with in late 1934, backing its 35-cent singles?
Decca
Decca's new American arm was run by Jack Kapp, who had managed Crosby's old label, Brunswick; Kapp also coaxed him out of his jazzier mannerisms and into a clearer style.
Q 10Which weekly NBC radio show did Crosby host from 1936 for a decade?
Kraft Music Hall
Kraft Music Hall also made a star of comedian Bob Burns, whose home-made horn, the 'bazooka', later gave its name to the Army's wartime rocket launcher.
Q 11Which jazz trumpeter did Crosby insist be hired, and prominently billed, for the 1936 film Pennies from Heaven?
Louis Armstrong
Louis Armstrong got both the part and his special billing only because Crosby insisted on them; twenty years later the two friends traded verses on 'Now You Has Jazz' in High Society.
Q 12Which invention let Crosby swap the stage shout for his soft crooning?
The microphone
The microphone picked up every quiet inflection, so Crosby could sing as if to one listener; earlier stars had to belt their songs to reach the back rows unaided.
Q 13Crosby first sang 'White Christmas' on radio at Christmas 1941, weeks after which event?
Pearl Harbor attack
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 grew out of a dinner at Crosby's house: when one of his children balked at going to school, Crosby warned he might grow up to be a mule, and Jimmy Van Heusen heard a song in it.
Q 22The first of the Crosby-Hope buddy pictures, in 1940, took them on the road to where?
Singapore
Singapore was only the start: six more Road comedies followed over the next 22 years, and an eighth, Road to the Fountain of Youth, was being planned when Crosby died in 1977.
Q 23Who was the female lead in all but the last of the Road films?
Dorothy Lamour
The Pearl Harbor attack was under three weeks old when he sang it on NBC; the following May he recorded the song in a session that took just 18 minutes.
Q 14Who wrote 'White Christmas'?
Irving Berlin
Irving Berlin knew what he had: he is said to have hurried into his office and asked his secretary to take down 'the best song anybody ever wrote'.
Q 15Why did Crosby re-record 'White Christmas' in 1947?
A worn-out master
A worn-out master: the 1942 original had been damaged by heavy use, so he remade the record with the same orchestra and chorus, and that 1947 take is the one usually heard today.
Q 16Which comedian co-starred with Crosby in the 1954 film White Christmas after Fred Astaire turned the part down?
Danny Kaye
Danny Kaye was the third choice: Fred Astaire declined, Donald O'Connor fell ill just before shooting began, and Kaye stepped in at short notice.
Q 17Which 1942 film, co-starring Fred Astaire, first put 'White Christmas' on screen?
Holiday Inn
Holiday Inn left a second legacy: in 1952 the architect drawing up Kemmons Wilson's first motel wrote the film's title on the plans as a joke, and the hotel chain kept it.
Q 18For which 1944 film did Crosby win the Academy Award for Best Actor?
Going My Way
Going My Way won Crosby an Oscar made of painted plaster: metal was short in wartime, and winners were invited to swap their statuettes for gold-plated ones once peace came.
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
Playing the same character, Father O'Malley, in a sequel brought the second nomination; this time he lost, to Ray Milland's alcoholic writer in The Lost Weekend.
Q 20Which Irish actor played the crusty old pastor opposite Crosby's young 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, Hollywood's 'Sarong Queen', was the woman both men chased through six Road films; in the seventh she was cut back to a cameo and a single song.
Q 24Crosby earned his third Oscar nomination playing an alcoholic has-been actor in which 1954 film?
The Country Girl
The Country Girl cast both stars against type: Crosby as a washed-up drinker, and Grace Kelly, stripped of her glamour, as his dowdy wife, the part that won her the Best Actress Oscar.
Q 25High Society (1956), starring Crosby, Grace Kelly and Frank Sinatra, was a musical remake of which film?
The Philadelphia Story
The Philadelphia Story gained Cole Porter songs and moved to Newport; it was Grace Kelly's last film, released three months after she married Prince Rainier and gave up acting at 26.
Q 26Which star ended Crosby's five-year run as top box-office draw in 1949?
Bob Hope
Bob Hope, his sparring partner in the Road comedies, was voted the top draw of 1949 by America's cinema owners, who had put Crosby first every year since 1944.
Q 27Which company did Crosby back with $50,000 to build tape recorders based on a captured German machine?
Ampex
Ampex put Crosby's money into production of its recorders; in 1949 he left one at the house of guitarist Les Paul, who added an extra head and used it to pioneer sound-on-sound recording.
Q 28Bing Crosby Enterprises gave the first demonstration of what technology in November 1951?
Videotape recording
Videotape recording was Crosby's next goal after taping his radio shows, but the pictures his engineers showed in 1951 were blurred, and the first practical machine came from another firm in 1956.
Q 29Crosby held stock in which juice company and plugged it on a weekday radio show from 1948?
Minute Maid
Minute Maid had lost money for two years with little cash to advertise; then Crosby began spinning records and pitching its frozen orange juice on the radio five mornings a week.
Q 30Crosby was a part-owner of which baseball team from 1946 until his death?
Pittsburgh Pirates
Pittsburgh Pirates: he could not bear to watch Game 7 of the 1960 World Series, so he had the telecast filmed; found in his wine cellar in 2009, it is the only complete copy.