The seasonal giant everyone knows
'White Christmas' is the gimme almost anyone can name. The trivia is placing it to 1942's Holiday Inn, not the later film named after the song.
Bing Crosby Quiz: Guess the Song & Test Your Trivia
Test your knowledge of Bing Crosby's biggest hits, deep cuts and iconic moments.
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Bing Crosby at a glance
- Main genre
- Traditional pop and vocal standards
- Real name
- Harry Lillis "Bing" Crosby
- Best-known songs to guess
- White Christmas, Swinging on a Star, Pennies from Heaven
- Deep cuts fans miss
- Don't Fence Me In, I've Got a Pocketful of Dreams, Peace on Earth / Little Drummer Boy (with David Bowie)
- Eras in the quiz
- 1930s crooning, 1940s film musicals, the 1950s Christmas standard
- Also known for
- Oscar-winning actor in Going My Way (1944) and an early backer of tape recording
- Related artists
- Judy Garland · Glenn Miller · Duke Ellington
- Quiz difficulty
- Easy on 'White Christmas', harder placing his film songs to the right movie and year
Guess the Bing Crosby Song
'White Christmas', 'Swinging on a Star' and 'Pennies from Heaven' are the ones most players name on the first bar.
- 01
White Christmas
- 02
Swinging on a Star
- 03
Pennies from Heaven
- 04
Don't Fence Me In
- 05
I've Got a Pocketful of Dreams
- 06
Peace on Earth / Little Drummer Boy
- 07
The Preacher
- 08
I Wish You A Merry Christmas
Bing Crosby Trivia: The Voice That Taught Sinatra
One of the best-selling singles of all time, an acting Oscar, and the tape-recording gamble that changed radio.
- 'White Christmas', which Crosby introduced in the 1942 film Holiday Inn, is recognized as one of the best-selling singles of all time. It anchors the 1940s in a quiz on music by decade.
- Crosby helped pioneer intimate crooning, singing softly into the microphone instead of belting, a style that shaped Frank Sinatra and countless singers after him. Crooner fans can keep going with a music genre quiz.
- He won the Academy Award for Best Actor for playing a priest in 1944's Going My Way, the film in which he sang 'Swinging on a Star'.
- Crosby was an early supporter of magnetic tape recording; he invested in and backed Ampex's tape-recorder development after the war so he could pre-record his radio show rather than perform it live.
- His 1977 duet with David Bowie, 'Peace on Earth / Little Drummer Boy', recorded weeks before Crosby's death, became a surprise holiday classic.
How Well Do You Know Bing Crosby's Hits?
Naming 'White Christmas' is easy; placing his film songs to the right movie and year is the real test.
Crooner or actor, the double career
Crosby won a Best Actor Oscar for Going My Way and sang 'Swinging on a Star' in it. His film numbers are a quiz territory of their own.
The voice that taught Sinatra
Crosby's soft microphone delivery set the template for Frank Sinatra and the crooners who followed. A round may ask who influenced whom across that lineage.
The duets and covers that outlived him
From 'Pennies from Heaven' becoming a standard to the 1977 duet with David Bowie, Crosby turns up in places players do not expect.
About Bing Crosby
The crooner behind 'White Christmas', one of the best-selling singles ever made. His soft microphone style shaped Frank Sinatra and modern pop singing.
Two things collide in a Bing Crosby quiz: the songs everyone knows and the films they came from. His voice is also an easy pick in guess the artist rounds. Guess the Bing Crosby song from 'White Christmas' and 'Swinging on a Star' to 'Pennies from Heaven', then test your trivia on the crooner who sang one of the best-selling singles of all time and taught the microphone to whisper. Trace the soft style that shaped Frank Sinatra, place each hit in the movie it came from, and find out how well you know the voice that ran popular radio for two decades. Then challenge your friends to name the film too.
Bing Crosby Quiz FAQ
What can I expect from the Bing Crosby quiz?
Clips of his best-known recordings to name, then trivia on his film songs, his crooning style, and the era each hit comes from.
Which Bing Crosby songs come up?
'White Christmas', 'Swinging on a Star' and 'Pennies from Heaven', along with numbers like 'Don't Fence Me In' and his David Bowie duet.
What makes the Bing Crosby quiz challenging?
Many hits come from his films, so placing a song to the right movie and year is often harder than naming the tune.
Why is Bing Crosby important to pop singing?
He was among the first to sing softly into the microphone, a crooning style that directly shaped Frank Sinatra and later pop vocalists.
Who was Bing Crosby?
Harry Lillis 'Bing' Crosby (1903-1977), an American singer and actor who won a Best Actor Oscar and sold records by the hundreds of millions.
Is the Bing Crosby quiz free to play?
Yes, every round is free on Songtrivia, with no signup and no Spotify account required. You can also guess the song with friends in a multiplayer music quiz.
Sources & methodology
Sources consulted
Wikipedia · AllMusic · Pitchfork · Billboard · Songtrivia editorial team.
Our methodology
Each topic is curated by a Quiz Master with category expertise. Selection crosses cultural impact, chart performance, recognition potential and era variety.