Tony Bennett Trivia
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67 free Tony Bennett trivia questions with answers — music quiz, new questions added Oct 2026.
This Tony Bennett trivia quiz follows Anthony Benedetto from singing waiter in Queens and infantryman in Germany to "Because of You", the Fairmont Hotel, the lost years and the comeback that made him an MTV star at 68 and a chart-topper at 88 with Lady Gaga. The easy questions cover his real name, San Francisco, the Grammys, Gaga and his Alzheimer's diagnosis. Medium questions dig into Mitch Miller, Count Basie, Ralph Sharon, Selma, Bill Evans, Danny Bennett's management and MTV Unplugged. The hard and expert questions are for people who own the 73-CD box: Joe Bari, Tennessee Ernie Ford, the Once Upon a Time B-side, Quacky Duck, Improv Records, Talk of the Town, the Kentucky Derby commission and Homage to Hockney. Every answer was checked against a reference page and each question carries its citation, so the dates, chart positions and names can be trusted. Difficulty is shown on every question, which makes it easy to build a round for a music quiz night or play the whole set. When you finish, try our Frank Sinatra and other Great American Songbook quizzes.
30 of 67 questions with answers and explanations. Play the quiz
Q 01The Broadway and Hollywood standards Bennett sang all his life are known as the Great American what?
Songbook
Songbook is the word: he resisted pressure to trade those standards for passing fashions, and in the 1990s a generation raised on rock embraced him exactly as he was.
Q 02In which New York City borough was Tony Bennett born?
Queens
Queens was home: he grew up poor in Astoria, the son of a grocer who died when he was ten, and watched his mother work all hours to support three children.
Q 03Bennett played himself in an episode of which animated series, crooning an ode to 'Capital City'?
The Simpsons
The Simpsons cast him as himself in 'Dancin' Homer'; cartoons, late-night talk shows and MTV were all part of a deliberate push to introduce him to listeners raised on rock.
Q 04Bennett likened being pushed to record rock hits to his seamstress mother being forced to make what?
A cheap dress
A cheap dress was his comparison: as a boy he had watched his mother, sewing piecework to feed three children, refuse to work on bad ones, and he felt the same way about songs.
Q 05Which pop star did Bennett collaborate with on the albums Cheek to Cheek and Love for Sale?
Lady Gaga
Lady Gaga was almost 60 years his junior; their first album of standards went straight to No. 1 in the US, and she shared the stage for the two 2021 shows that proved his last.
Q 06Which illness did Bennett reveal in February 2021 that he had been living with since 2016?
Alzheimer's
Alzheimer's did not stop the music: he went on recording and performing for five years after the diagnosis, and told fans, 'Life is a gift, even with Alzheimer's.'
Q 07Bennett's 1951 hit "Cold, Cold Heart" was a cover of a song by which country star?
Hank Williams
Hank Williams had just taken it to the top of the country chart; Bennett's orchestral version went to No. 1 on the pop chart and gave a Williams song its first pop audience.
Q 08Bennett's 1953 single 'Stranger in Paradise' came from which Broadway musical that opened amid a newspaper strike?
Kismet
Kismet opened in the middle of a New York newspaper strike, which kept its critics out of print; by the time their reviews ran, not all of them kind, audiences had made it a hit, and 'Stranger in Paradise' became a pop hit as well.
Q 09Which stage name was the young singer using before a famous comedian renamed him Tony Bennett?
Joe Bari
Joe Bari was the name on his early nightclub bills; the comedian who hired him disliked it, judged his real name too long for a marquee, and told him, 'We'll call you Tony Bennett.'
Q 10Which comedian put the young singer in his New York stage show and renamed him Tony Bennett?
Bob Hope
Bob Hope disliked the singer's stage name and thought his real one too long for a marquee, so, as Bennett told it, he paused and said, 'We'll call you Tony Bennett.'
Q 11Which Columbia Records producer signed Bennett in 1950 and oversaw his first number-one hits?
Mitch Miller
Mitch Miller and Bennett clashed for years: the hit-maker kept pushing novelty songs and gimmicks, the singer kept resisting, and together they still turned out number-one records.
Q 12Which bandleader's orchestra backed Bennett on two late-1950s albums, including In Person!?
Count Basie
Count Basie's band brought the pop hit-maker before a jazz audience, and Frank Sinatra would later record with the same orchestra too.
Q 13Which pianist spent decades as Bennett's accompanist and musical director and steered him toward jazz?
Ralph Sharon
Q 21Which 1965 Bennett single came from Pickwick, a West End musical based on a Dickens novel?
If I Ruled the World
If I Ruled the World got a second life four decades after the hit version, when Bennett recut it as a duet with Celine Dion.
Q 22Bennett answered Harry Belafonte's call and sang for the marchers at which civil-rights protest?
The Selma to Montgomery marches
The Selma to Montgomery marches ended for him with a lift to the airport from volunteer Viola Liuzzo, who was shot dead by Klansmen later that day.
Q 23Which record executive pushed Bennett into a 1970 album of rock-era covers that made him physically sick?
Clive Davis
Ralph Sharon also supplied the signature song: its sheet music lay forgotten in his shirt drawer for more than a year until he packed for a tour and found it.
Q 14Where did Bennett first sing his signature song in December 1961?
The Fairmont's Venetian Room
The Fairmont's Venetian Room heard it first: his pianist thought the ballad would please that one booking, and both men expected a local hit at most.
Q 15Bennett's signature song was originally the B-side of which single?
Once Upon a Time
Once Upon a Time was the side Columbia promoted; the flip was expected to be a regional crowd-pleaser at most, yet it won Record of the Year and became the song of his life.
Q 16As a boy, Bennett sang at the opening of which New York bridge, standing beside Mayor Fiorello La Guardia?
The Triborough Bridge
The Triborough Bridge opened in 1936 with its longest span landing in Astoria, his own neighbourhood, where the schoolboy had already drawn notice for his singing.
Q 17On Arthur Godfrey's Talent Scouts, the young Bennett finished runner-up to which future star?
Rosemary Clooney
Rosemary Clooney took first place, but second was enough to get the unknown singer noticed, and within a few years both were making hits for the same label.
Q 18Which news agency employed the teenage Bennett as a copy boy after he dropped out of school?
The Associated Press
The Associated Press job came after he quit a school where he had been training to be a commercial artist, not a singer; his mother needed the wages.
Q 19Whose celebrated Carnegie Hall concert came a year before Bennett's own there in 1962 and also became a hit live album?
Judy Garland
Judy Garland's show capped her great comeback and became her biggest-selling album; Bennett's own concert was recorded too and released as a live album.
Q 20Bennett was a guest on which host's very first Tonight Show, in October 1962?
Johnny Carson
Johnny Carson's debut also had Groucho Marx, Joan Crawford and Mel Brooks, yet no footage of the night survives: only photographs and a fan's audio tape.
Clive Davis, then head of Columbia, wanted contemporary material, so Bennett sang Beatles songs behind a psychedelic sleeve; within two years he had left the label.
Q 24What was the name of the record label Bennett founded in the 1970s?
Improv
Improv never had a major label to distribute its jazz albums, and it folded in 1977, leaving its founder with no record deal at all.
Q 25With which jazz pianist did Bennett record two acclaimed voice-and-piano albums in the mid-1970s?
Bill Evans
Bill Evans and Bennett recorded as a bare duo, no band at all; neither album charted, yet both are now counted among the finest work of Bennett's career.
Q 26After a near-fatal 1979 overdose, which relative became Bennett's manager and engineered his comeback?
His son Danny
His son Danny cut his spending, moved him back to New York and booked him into colleges and small theatres to shake off a tired Las Vegas image.
Q 27Regular appearances on which late-night host's show helped win Bennett a college-age audience when he was in his sixties?
David Letterman
David Letterman's hip young viewers were the target: his manager bet that the suit, the trio and the old songs needed no changing at all, only new listeners.
Q 28Which composer wrote 'Life in a Looking Glass', the Academy Award-nominated song Bennett sang for Blake Edwards's That's Life!?
Henry Mancini
Henry Mancini was the director's regular composer and wrote the Pink Panther theme for him; this song lost the award to 'Take My Breath Away' from Top Gun.
Q 29Bennett's 1993 album Steppin' Out was a tribute to which entertainer?
Fred Astaire
Fred Astaire's film songs filled the album, and its video for 'Steppin' Out with My Baby' was picked for MTV's Buzz Bin, beside the rock hits of 1993.
Q 30Which two guests joined Bennett on his 1994 MTV Unplugged special?
Elvis Costello and k.d. lang
Elvis Costello and k.d. lang each joined him for a duet; lang went on to tour with him and to share a whole album, the first he ever made with another singer.