Frank Sinatra Trivia
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110 free Frank Sinatra trivia questions with answers — music quiz, new questions added Oct 2026.
63 free Frank Sinatra trivia questions with answers. Frank Sinatra's life ran from a Hoboken tenement to the Chairman of the Board, and this quiz follows the whole arc. The questions cover the Harry James and Tommy Dorsey bands, the bobby soxers and the Columbus Day Riot, the Capitol comeback with Nelson Riddle, founding Reprise, the Rat Pack and the Summit at the Sands, the Oscar for From Here to Eternity, the Manchurian Candidate, four marriages, the kidnapping of Frank Jr., the Kennedy snub, My Way and New York, New York, the 1971 retirement and the 1973 comeback, Duets, and the honors that piled up before the Las Vegas lights were dimmed in 1998. Easy questions ask where he was born and which film won him his Oscar; the hard ones want the ransom paid for Frank Jr., the football club he was buried in the colours of, and who recorded a rejected English version of the song that became My Way before Paul Anka did. Made for people who own more than one Sinatra record and want to argue about the best one. Every answer was checked against Wikipedia's articles on Sinatra, his albums, films, family and the Rat Pack, and each question carries the sentence that backs it up. Song titles come up throughout; lyrics do not.
30 of 110 questions with answers and explanations. Play the quiz
Q 01In which New Jersey waterfront city was Frank Sinatra born in 1915?
Hoboken
Hoboken was where his mother Dolly ran an Italian ward for the Democratic machine and could deliver 600 votes at election time; her pull later helped land Frank an early singing job.
Q 02Which Sinatra recording was on the mixtape astronaut Gene Cernan carried around the Moon on Apollo 10?
Fly Me to the Moon
Fly Me to the Moon was first recorded in 1954 under the title 'In Other Words'; ten years later Sinatra's version tied it so closely to the Apollo flights that astronauts took it along.
Q 03In 1935 Sinatra got his first break singing with a local quartet on which national radio show?
Major Bowes Amateur Hour
Major Bowes Amateur Hour gave the quartet first prize and a place on a Bowes touring show; the trio had let Sinatra join partly because he owned a car and could drive them to gigs.
Q 04Which trumpet-playing bandleader signed Sinatra to his first band contract in 1939, at $75 a week?
Harry James
Harry James wanted to bill him as 'Frankie Satin', thinking Sinatra sounded too Italian; the singer refused to change his name, and within months he had left for a bigger band.
Q 05Which bandleader made Sinatra sign away a large share of his future earnings before letting him go solo in 1942?
Tommy Dorsey
Tommy Dorsey's cut is put at a third or more of Sinatra's income for years ahead, until the singer's record label and booking agency bought the contract out; Sinatra said only Dorsey and his own mother ever scared him.
Q 06Which 1940 ballad, written by a young widow in memory of her husband, gave Sinatra his first chart-topping record?
I'll Never Smile Again
I'll Never Smile Again was recorded first by Glenn Miller, but the hushed version Sinatra sang with the Pied Pipers was the hit, topping Billboard's new best-sellers chart for twelve weeks.
Q 07Sinatra's screaming teenage-girl fans of the 1940s were known by what name?
Bobby soxers
Bobby soxers took their name from their ankle socks; his press agents later admitted hiring a dozen girls to scream and swoon, only to find hundreds more doing it for free.
Q 08The 1944 'Columbus Day Riot' by thousands of shut-out Sinatra fans erupted outside which New York venue?
The Paramount Theatre
The Paramount Theatre in Times Square had a queue from midnight; few of those inside would give up their seats between shows, so some 30,000 fans left outside ran wild.
Q 09Bandmates nicknamed the compulsively clean young Sinatra after which Shakespeare character?
Lady Macbeth
Lady Macbeth, the hand-washing queen of the Scottish play, was the nickname; he showered constantly and changed outfits so often that it stuck.
Q 10Which 1946 album, Sinatra's first, went to the top of the Billboard chart?
The Voice of Frank Sinatra
The Voice of Frank Sinatra took its title from the nickname the young crooner already carried; it first came as four 78-rpm discs, and Columbia later reissued it as its first pop LP.
Q 11Sinatra won his Academy Award for playing Private Maggio in which 1953 film?
From Here to Eternity
From Here to Eternity won him the Best Supporting Actor Oscar; the role revived a career that had bottomed out a year earlier, when he played to half-empty rooms and a Hawaiian county fair.
Q 12In The Man with the Golden Arm (1955), Sinatra plays a man struggling with what?
Heroin addiction
Heroin addiction, though the film never names the drug, cost it a Production Code seal; it was released anyway, drew crowds, and a year later the Code's ban on drug stories was dropped.
Q 13Which arranger, then Nat King Cole's musical director, shaped Sinatra's Capitol classics from 1953 on?
Nelson Riddle
Q 21Which Rat Pack member, a brother-in-law of JFK, was frozen out by Sinatra in 1962?
Peter Lawford
Peter Lawford was blamed for failing to change the Kennedys' minds about a 1962 visit to Sinatra's home; he was dropped from the Rat Pack, and his part in Robin and the 7 Hoods went to another crooner.
Q 22Which tycoon's takeover of the Sands ended Sinatra's unlimited casino credit and, after a 1967 brawl, his years there?
Howard Hughes
Howard Hughes's managers refused him credit; Sinatra reportedly drove a golf cart through a window, casino boss Carl Cohen knocked the caps off his front teeth, and he took his act to Caesars Palace.
Q 23Which Cold War thriller did Sinatra consider the high point of his film career?
Nelson Riddle arranged 'I've Got the World on a String' in April 1953; after hearing the playback Sinatra exclaimed 'I'm back, baby, I'm back!'
Q 14Sinatra's 1955 LP In the Wee Small Hours is frequently described as one of the first examples of what?
A concept album
A concept album, built around lost love and late nights, is how it is usually described; its mood is often read as a response to the collapse of his second marriage.
Q 15Which songwriter wrote 'I've Got You Under My Skin', Sinatra's 1956 recording with the trombone solo?
Cole Porter
Cole Porter wrote it in 1936; twenty years on, Sinatra kept calling for one more take, far past his usual four or five, while trombonist Milt Bernhart feared he had already used up his best solo.
Q 16Sinatra's 1958 album Come Fly with Me was built on what idea?
A musical trip around the world
A musical trip around the world runs from 'Brazil' to 'Isle of Capri'; Sinatra disliked the cover, complaining that it looked like an advertisement for the airline TWA.
Q 17In 1960 Sinatra left Capitol Records to found which label of his own?
Reprise
Reprise was the label; he first tried to buy the jazz label Verve from Norman Granz, and only started his own after that deal fell through.
Q 18Which nickname did New York disc jockey William B. Williams give Sinatra?
The Chairman of the Board
The Chairman of the Board is said to have come to Williams on his radio show: Benny Goodman was a king and Ellington a duke, he mused, so Sinatra needed a title too, and the name stuck.
Q 19In Ocean's 11 (1960), Danny Ocean's crew robs five casinos on which night?
New Year's Eve
New Year's Eve: at midnight they black out the casinos and empty the cashier cages, then hide the loot in a dead partner's coffin, only for the body to be cremated, cash and all.
Q 20The original 1950s Rat Pack met at the Holmby Hills home of which Hollywood couple?
Humphrey Bogart and Lauren Bacall
Humphrey Bogart and Lauren Bacall hosted the circle at their Holmby Hills home; Bacall reportedly greeted the men back from Las Vegas with 'You look like a goddamn rat pack.'
The Manchurian Candidate
The Manchurian Candidate was a political satire no studio wanted; its screenwriter recalled that United Artists agreed to make it only once Sinatra signed on to play Major Marco.
Q 24Shooting a 1962 karate fight with Henry Silva, Sinatra struck a table and broke what?
His little finger
His little finger broke on the table; he went on filming without having the hand properly set, and it gave him trouble for the rest of his life.
Q 25Which member of Sinatra's family was kidnapped at Lake Tahoe in 1963?
His son, Frank Jr.
His son, Frank Jr., was freed after two days; Sinatra had offered $1 million, but the kidnappers asked for only about a quarter of that, and all three were soon caught.
Q 26After kidnappers made him take their ransom calls at payphones in 1963, what did Sinatra carry for life?
Ten dimes
Ten dimes went everywhere with him afterward, since he had worried during the ransom calls that he would run out of coins; ten dimes went into his coffin too.
Q 27In 1962 President Kennedy snubbed Sinatra by staying at whose Palm Springs-area estate instead?
Bing Crosby
Bing Crosby, a staunch Republican, got the president because Kennedy's advisers feared Sinatra's mob friendships; Sinatra had built a helipad for the visit and reportedly took a sledgehammer to it.
Q 28Sinatra's Nevada gaming license was suspended in 1963 after which mobster was seen at his Cal Neva Lodge?
Sam Giancana
Sam Giancana, the Chicago boss, was spotted at Cal Neva; Sinatra agreed to give up his shares in both Cal Neva and the Sands, and the license was not restored until 1981.
Q 29Which actress, married to Sinatra from 1951 to 1957, later called him the love of her life?
Ava Gardner
Ava Gardner stayed close to him long after the 1957 divorce; when a stroke left her ailing in London three decades later, he arranged a medically staffed private plane to take her to a specialist.
Q 30Which 21-year-old actress married the 50-year-old Sinatra in July 1966?
Mia Farrow
Mia Farrow left the hit soap Peyton Place at Sinatra's urging before the July 1966 wedding; her insistence on keeping her film career angered him, and they divorced in 1968.