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70 free Tony Bennett trivia questions with answers — music quiz, new questions added Aug 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 70 questions with answers and explanations. Play the quiz
Q 01What was Tony Bennett's real name?
Anthony Dominick Benedetto
He signed his paintings Benedetto throughout his life.
Q 02In which New York City borough was Tony Bennett born?
Queens
He was born at St. John's Hospital in Long Island City in 1926.
Q 03Bennett's signature song is about leaving his heart in which city?
San Francisco
He first sang it in the Fairmont Hotel's Venetian Room in December 1961.
Q 04How many Grammy Awards did Tony Bennett win?
20
He also won two Primetime Emmys and a Kennedy Center Honor.
Q 05Which pop star did Bennett collaborate with on the albums Cheek to Cheek and Love for Sale?
Lady Gaga
They met at a Robin Hood Foundation gala in 2011.
Q 06Which illness did Bennett reveal in February 2021 that he had been living with since 2016?
Alzheimer's
His long-term memory stayed intact and he could still sing his whole repertoire.
Q 07What was Bennett's first No. 1 hit in 1951?
Because of You
His family said it was also the last song he sang before he died.
Q 08Bennett's 1951 hit "Cold, Cold Heart" was a cover of a song by which country star?
Hank Williams
It helped introduce Williams and country music to a wider national audience.
Q 09Bennett's 1953 'Stranger in Paradise' promoted which musical during a newspaper strike?
Kismet
It became a UK No. 1 a year and a half later.
Q 10Under what stage name did Bennett sing with an Army band in Germany and make his first recordings?
Joe Bari
Bob Hope later shortened Benedetto to Tony Bennett.
Q 11Which comedian took the young singer on the road in 1949 and shortened his name to Tony Bennett?
Bob Hope
Pearl Bailey had invited Hope to see him open for her in Greenwich Village.
Q 12Which producer signed Bennett to Columbia Records in 1950 and warned him not to imitate Sinatra?
Mitch Miller
Miller and arranger Percy Faith crafted all of his early hits.
Q 13Bennett was the first male pop vocalist to sing with which bandleader's orchestra?
Count Basie
The 1959 albums Strike Up the Band and In Person! came out of the partnership.
Q 21Bennett sang on the very first broadcast of which TV programme in October 1962?
The Tonight Show Starring Johnny Carson
He would later win over a new generation on Letterman and MTV.
Q 22What was Bennett's last top-40 single, a 1965 song from the musical Pickwick?
If I Ruled the World
The British Invasion was pushing standards singers off the charts.
Q 23Bennett took part in which 1965 civil-rights event, performing at the "Stars for Freedom" rally?
The Selma to Montgomery marches
Q 14Which pianist became Bennett's musical director in 1957 and steered him toward jazz?
Ralph Sharon
He brought "I Left My Heart in San Francisco" to Bennett and stayed with him until 2002.
Q 15Where did Bennett first sing his signature song in December 1961?
The Fairmont's Venetian Room
An 8-foot statue of Bennett was unveiled outside the Fairmont for his 90th birthday.
Q 16Bennett's signature song was originally the B-side of which single?
Once Upon a Time
DJs flipped the record over and the B-side became the hit.
Q 17Who wrote Bennett's signature song?
George Cory and Douglass Cross
They were two homesick amateur writers who had moved from San Francisco to New York.
Q 18Which country singer turned down Bennett's signature song before he recorded it?
Tennessee Ernie Ford
It had been written for opera singer Claramae Turner, who never recorded it.
Q 19What was the Billboard Hot 100 peak of Bennett's signature song?
19
Despite the modest peak it spent almost a year on various charts and won Record of the Year.
Q 20Bennett's 1962 Carnegie Hall concert made him only the second pop singer to headline there, after whom?
Judy Garland
He sang 44 songs with a band including Al Cohn and Kenny Burrell.
Viola Liuzzo drove him to the airport afterwards and was murdered by the KKK that day.
Q 24Which 1970 album of Beatles covers made Bennett physically ill at the thought of recording it?
Tony Sings the Great Hits of Today!
Clive Davis had pushed him to sing contemporary rock songs.
Q 25What was the name of the record label Bennett founded in the mid-1970s?
Improv
It made two acclaimed albums with Bill Evans but folded in 1977 for lack of distribution.
Q 26With which jazz pianist did Bennett make two acclaimed albums in 1975 and 1976?
Bill Evans
The Tony Bennett/Bill Evans Album and Together Again came out on Bennett's own label.
Q 27After a near-fatal 1979 overdose, which relative became Bennett's manager and engineered his comeback?
His son Danny
He booked his father in colleges and on Letterman to reach a younger crowd.
Q 28What was the name of Danny and Dae Bennett's floundering band before Danny turned to management?
Quacky Duck and His Barnyard Friends
Danny realised he had no musical talent but a head for business.
Q 29Which composer wrote Bennett's Oscar-nominated song "Life in a Looking Glass" from That's Life (1986)?
Henry Mancini
It was the theme of Blake Edwards's movie.
Q 30Bennett's 1993 album Steppin' Out was a tribute to which entertainer?
Fred Astaire
Its video got MTV airplay alongside the Red Hot Chili Peppers.