50 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 50 questions with answers and explanations. Play the quiz
Q 01In which Washington State city was Bing Crosby born in 1903?
Tacoma
The family moved to Spokane three years later, where he grew up and where his boyhood home now stands on the Gonzaga campus.
Q 02What was Bing Crosby's real first name?
Harry
He was Harry Lillis Crosby Jr., the fourth of seven children of a bookkeeper and an Irish-American mother.
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
He played on its baseball team as a freshman; the campus now houses his boyhood home as a museum, Oscar included.
Q 05Which instrument did Crosby play in the Musicaladers, his first band in Spokane?
Drums
His bandmate Al Rinker went with him to California in 1925.
Q 06Crosby's first big break came when he and Al Rinker were hired in 1926 by which bandleader?
Paul Whiteman
They earned 150 dollars a week and debuted with the orchestra at Chicago's Tivoli Theatre that December.
Q 07Crosby, Al Rinker and Harry Barris performed as which vocal trio?
The Rhythm Boys
Barris, a pianist and songwriter, joined in 1927; 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
He was still with the Whiteman organisation, recording alongside Bix Beiderbecke and the Dorsey brothers.
Q 09Which record company did Crosby sign with in late 1934, backing its 35-cent singles?
Decca
Founder Jack Kapp also talked Crosby into dropping his jazzier mannerisms for a cleaner vocal style.
Q 10Which weekly NBC radio show did Crosby host from 1936 for a decade?
Kraft Music Hall
His whistled theme song was '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
Studio boss Harry Cohn had baulked at paying Armstrong's air fare; the two men later sang 'Now You Has Jazz' in High Society.
Q 12Crosby's intimate singing style, made possible by the microphone, earned which popular label?
Crooner
He took popular singing beyond the shouting style of Al Jolson, who had to reach the back rows unamplified.
Q 13Crosby first performed 'White Christmas' on his radio show a few weeks after Pearl Harbor. On what date?
25 December 1941
It came a few weeks after Pearl Harbor; he recorded it for Decca the following May in just 18 minutes.
Q 21Which Oscar-winning song does the choir sing in Going My Way?
Swinging on a Star
Crosby introduced four Best Original Song winners in all, starting with 'Sweet Leilani' in 1937.
Q 22How many 'Road to...' films did Crosby make with Bob Hope between 1940 and 1962?
Seven
Dorothy Lamour co-starred in six; Joan Collins replaced her in The Road to Hong Kong, though Lamour got a cameo.
Q 23The first of the Crosby-Hope buddy pictures, in 1940, took them on the road to where?
Singapore
A final Road film, in which the trio would hunt for the Fountain of Youth, was being planned when Crosby died.
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
The version usually heard today is a 1947 re-recording, made because 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'
He was associated with the song for the rest of his life regardless.
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
He played Father O'Malley; the film was the year's top earner and won seven Oscars including 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
His co-star in the sequel was Ingrid Bergman; five other actors have since matched the feat.
Q 20Who played the elderly priest opposite Crosby in Going My Way?
Barry Fitzgerald
Director Leo McCarey and Crosby later presented a copy of the film to Pope Pius XII.
Q 24Who was the female lead in six of the seven Road films?
Dorothy Lamour
Crosby felt she had grown too old for The Road to Hong Kong; Hope refused to make it without her.
Q 25Crosby earned his third Oscar nomination playing an alcoholic has-been actor in which 1954 film?
The Country Girl
Grace Kelly won Best Actress as his long-suffering wife; William Holden co-starred.
Q 26High Society (1956), starring Crosby, Grace Kelly and Frank Sinatra, was a musical remake of which film?
The Philadelphia Story
Cole Porter wrote the songs and Louis Armstrong appeared; the story was moved to Newport, Rhode Island.
Q 27Crosby was the number one box-office attraction for five consecutive years. Which years?
1944-1948
In 1946 he starred in three of the year's five highest-grossing films.
Q 28Bing Crosby invested $50,000 in which company to build tape recorders after seeing a captured German machine?
Ampex
He became the first performer to pre-record his radio shows on tape, and gave an early machine to Les Paul, who invented multitrack recording with it.
Q 29Bing Crosby Enterprises gave the first demonstration of what technology in November 1951?
Videotape recording
The images were 'blurred and indistinct', produced on a modified Ampex audio recorder running tape at 360 inches per second.
Q 30Crosby made a fortune as a principal stockholder in which juice company?
Minute Maid
His family's Hillsborough home served as the set for some of the brand's TV commercials.