110 Fun Facts About Frank Sinatra

In which New Jersey waterfront city was Frank Sinatra born in 1915?

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.

Which Sinatra recording was on the mixtape astronaut Gene Cernan carried around the Moon on Apollo 10?

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.

In 1935 Sinatra got his first break singing with a local quartet on which national radio show?

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.

Which trumpet-playing bandleader signed Sinatra to his first band contract in 1939, at $75 a week?

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.

Which bandleader made Sinatra sign away a large share of his future earnings before letting him go solo in 1942?

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.

Which 1940 ballad, written by a young widow in memory of her husband, gave Sinatra his first chart-topping record?

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.

Sinatra's screaming teenage-girl fans of the 1940s were known by what name?

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.

The 1944 'Columbus Day Riot' by thousands of shut-out Sinatra fans erupted outside which New York venue?

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.

Bandmates nicknamed the compulsively clean young Sinatra after which Shakespeare character?

Lady Macbeth, the hand-washing queen of the Scottish play, was the nickname; he showered constantly and changed outfits so often that it stuck.

Which 1946 album, Sinatra's first, went to the top of the Billboard chart?

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.

Sinatra won his Academy Award for playing Private Maggio in which 1953 film?

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.

In The Man with the Golden Arm (1955), Sinatra plays a man struggling with what?

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.

Which arranger, then Nat King Cole's musical director, shaped Sinatra's Capitol classics from 1953 on?

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!'

Sinatra's 1955 LP In the Wee Small Hours is frequently described as one of the first examples of what?

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.

Which songwriter wrote 'I've Got You Under My Skin', Sinatra's 1956 recording with the trombone solo?

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.

Sinatra's 1958 album Come Fly with Me was built on what idea?

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.

In 1960 Sinatra left Capitol Records to found which label of his own?

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.

Which nickname did New York disc jockey William B. Williams give Sinatra?

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.

In Ocean's 11 (1960), Danny Ocean's crew robs five casinos on which night?

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.

The original 1950s Rat Pack met at the Holmby Hills home of which Hollywood couple?

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.'

Which Rat Pack member, a brother-in-law of JFK, was frozen out by Sinatra in 1962?

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.

Which tycoon's takeover of the Sands ended Sinatra's unlimited casino credit and, after a 1967 brawl, his years there?

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.

Which Cold War thriller did Sinatra consider the high point of his film career?

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.

Shooting a 1962 karate fight with Henry Silva, Sinatra struck a table and broke what?

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.

Which member of Sinatra's family was kidnapped at Lake Tahoe in 1963?

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.

After kidnappers made him take their ransom calls at payphones in 1963, what did Sinatra carry for life?

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.

In 1962 President Kennedy snubbed Sinatra by staying at whose Palm Springs-area estate instead?

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.

Sinatra's Nevada gaming license was suspended in 1963 after which mobster was seen at his Cal Neva Lodge?

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.

Which actress, married to Sinatra from 1951 to 1957, later called him the love of her life?

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.

Which 21-year-old actress married the 50-year-old Sinatra in July 1966?

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.

Sinatra had divorce papers served on his third wife while she was filming which horror movie?

Rosemary's Baby was the film; he had cast her in his own The Detective and, when she stayed on Polanski's set, gave the part to Jacqueline Bisset.

Which Sinatra duet with his daughter Nancy went to No. 1 on both sides of the Atlantic in 1967?

Somethin' Stupid came to Sinatra as another duo's record; he played it to Nancy's producer Lee Hazlewood, who told him that if he didn't sing it with her, Hazlewood would.

Sinatra's daughter Nancy scored a transatlantic No. 1 of her own in 1966 with which song?

These Boots Are Made for Walkin' was a song Lee Hazlewood sang himself until Nancy told him that from a man it sounded harsh and abusive, but from a girl it would be perfect.

Which French singer first recorded 'Comme d'habitude', the basis of Sinatra's 'My Way', in 1967?

Claude François co-wrote and recorded 'Comme d'habitude' in 1967; the French original is about the routine of a failing relationship, nothing like the defiant retrospective it became.

Who wrote the English lyrics of 'My Way' specifically with Sinatra in mind?

Paul Anka finished the lyric at 5 a.m. on an IBM electric typewriter and phoned Sinatra in Las Vegas to say he had something special.

Which future rock star wrote rejected English lyrics in 1968 for the French song that became 'My Way'?

David Bowie's version, 'Even a Fool Learns to Love', was never released; he later answered with 'Life on Mars?', built on much the same chords and marked 'inspired by Frankie' on the album sleeve.

What did Sinatra come to think of 'My Way', his signature song?

Self-indulgent and self-serving was his verdict, his daughter Tina said; the song stuck and, in her words, he couldn't get it off his shoe.

The 'Sinatra Doctrine', a 1989 nickname alluding to 'My Way', described which country's foreign policy?

The Soviet Union under Gorbachev was letting Warsaw Pact states go their own way, so foreign ministry spokesman Gennadi Gerasimov reached for the song in October 1989.

Which cartoon character's name came from Sinatra's scat singing at the end of 'Strangers in the Night'?

Scooby-Doo got his name when CBS executive Fred Silverman, sleepless on a red-eye flight, heard Sinatra scat 'doo-be-doo-be-doo' and decided the cartoon's dog should be the star.

In 1966 Sinatra's 'Strangers in the Night' knocked which band off the top of the US chart?

The Beatles lost the top spot to him for one week and then reclaimed it; Sinatra, at 50, hated the song that gave him the hit.

Sinatra's 1967 bossa nova album paired him with which Brazilian composer?

Antônio Carlos Jobim, composer of 'The Girl from Ipanema', sang and played guitar beside him; Sinatra had won the last two Album of the Year Grammys, but this one lost to Sgt. Pepper.

Sinatra closed his 1971 'retirement' concert with which saloon song, vanishing into the dark on its last line?

Angel Eyes ends with the words 'Excuse me while I disappear'; as he sang them the spotlight went out and he was gone, though the retirement itself lasted only two years.

Sinatra's 1973 album and its accompanying TV special shared what title?

Ol' Blue Eyes Is Back ended a retirement that had lasted only two years, and its title gave Sinatra the last of his show-business nicknames.

'Theme from New York, New York' was written for a 1977 Scorsese film and first performed by which singer?

Liza Minnelli got a stronger song than first planned: her co-star Robert De Niro found the original title number too weak, so songwriters Kander and Ebb wrote this one in its place.

Sinatra's 'New York, New York' became the post-game anthem at which team's home stadium?

The Yankees adopted it at Yankee Stadium; for years the Sinatra version played after wins and the film's original singer's after losses, until she complained.

Which president presented Sinatra, once a devoted Democrat, with the Presidential Medal of Freedom?

Ronald Reagan gave him the medal in 1985; Sinatra had staged John F. Kennedy's inaugural gala in 1961, then crossed the aisle to back Nixon and Reagan.

Which magazine published Gay Talese's famous 1966 profile 'Frank Sinatra Has a Cold'?

Esquire ran it in April 1966; Sinatra refused to be interviewed, so Talese spent three months shadowing his entourage instead.

Which character in The Godfather did Sinatra believe was based on him?

Johnny Fontane, the crooner whose career the Don rescues, was the character; Mario Puzo wrote that Sinatra shouted abuse and threatened him when they met at Chasen's.

Because Die Hard was based on a sequel to The Detective's source novel, Fox had to offer Sinatra which role?

John McClane was offered to Sinatra, then about 70, who turned it down; the part went the rounds of a string of bigger names before landing with television actor Bruce Willis.

Which 1965 war film, about American and Japanese troops stranded on one island, is the only one Sinatra directed?

None but the Brave was shot on the Hawaiian island of Kauai, where Sinatra nearly drowned while swimming on a day off and had to be rescued by co-star Brad Dexter.

In On the Town (1949) and one earlier MGM musical with Gene Kelly, Sinatra played what?

A sailor on shore leave was his part in Anchors Aweigh and On the Town alike; against his later image, Sinatra played the shy innocent who needed Kelly's help with girls.

Which 1956 MGM musical cast Sinatra as a tabloid reporter covering the wedding of Grace Kelly's heiress?

High Society remade The Philadelphia Story as a musical: Sinatra took the reporter's part that had won James Stewart an Oscar, in Grace Kelly's last film before she became Princess of Monaco.

Which song sung by Sinatra in A Hole in the Head (1959) won the Oscar for Best Original Song?

High Hopes, by Sammy Cahn and Jimmy Van Heusen, won the 1959 Oscar and was reworked with new lyrics as a campaign jingle for John F. Kennedy in 1960.

Which rock and roll star, whose music Sinatra had publicly scorned, was the guest of honor on his 1960 TV special?

Elvis Presley, just out of the Army, sang Sinatra's 'Witchcraft' while Sinatra sang 'Love Me Tender', a truce after Sinatra had called rock and roll a 'rancid smelling aphrodisiac'.

The guest singers on Sinatra's best-selling 1993 album Duets did what?

Recorded remotely over digital phone lines: Sinatra sang alone at Capitol and his partners added their halves from studios far away, which critics dismissed as an engineering stunt.

Which rock singer joined Sinatra on 'I've Got You Under My Skin' for the 1993 Duets album?

Bono sang his half standing on a couch in a Dublin studio; months later he presented Sinatra's Grammy Legend Award, and the telecast cut away from Sinatra's long speech for a commercial.

Which landmark was bathed in blue light as a tribute in the days after Sinatra died in 1998?

The Empire State Building's top was floodlit blue for three days, its owners calling it a silent tribute to the man whose 'New York, New York' had become the city's song.

Which actor did Sinatra call 'Mumbles' after losing two coveted 1950s film roles to him?

Marlon Brando won the lead in On the Waterfront after Sinatra thought he had a handshake deal for it, then took Sky Masterson in Guys and Dolls, leaving Sinatra to play Nathan Detroit.

What were Sinatra's reported final words as doctors fought to save him in May 1998?

"I'm losing" is what the family reported he said as his wife urged him to fight; his gravestone was first inscribed with a more hopeful line, the song title 'The Best Is Yet to Come'.

What happened on the Las Vegas Strip the night after Sinatra died in 1998?

The lights were dimmed for a minute the next night, after the city's tourism agency asked hotel-casinos to go dark at 8:30 for the headliner who had ruled the Sands.

A bottle of which whiskey, Sinatra's favorite, went into his coffin?

Jack Daniel's went into the coffin with him; Sinatra had said he was for anything that gets you through the night, be it prayer, tranquilizers or a bottle of Jack Daniel's.

Who played Sinatra in HBO's 1998 film The Rat Pack?

Ray Liotta played Sinatra; Joe Mantegna played Dean Martin and Don Cheadle played Sammy Davis Jr. in the same film.

The swimming pool at Twin Palms, Sinatra's 1947 Palm Springs house, is famously shaped like what?

A grand piano, though architect E. Stewart Williams always insisted the shape was an accident; Sinatra had asked him for a Georgian mansion and was talked into a low modern house instead.

Which birth injury officially kept Sinatra out of World War II?

A punctured eardrum: the forceps that pulled out the 13.5-pound newborn tore his ear, cheek and neck, and the eardrum was the reason later given for ruling him unfit for the draft.

Sinatra's father Marty, a former bantamweight boxer, rose to captain in which city service?

Fire department captain was the rank Marty reached after boxing as 'Marty O'Brien'; he and Dolly also ran a tavern under that name during Prohibition.

Which city does Sinatra salute in 'My Kind of Town', the song he introduced in Robin and the 7 Hoods?

Chicago is the town in question, as the lyric says; written by Sammy Cahn and Jimmy Van Heusen, the song was nominated for an Oscar but lost to 'Chim Chim Cher-ee' from Mary Poppins.

Which 1959 Sinatra album spent more than two years on the Billboard chart and won the Grammy for Album of the Year?

Come Dance with Me! took Album of the Year at the second Grammys; at the first, Only the Lonely lost that award to Henry Mancini's The Music from Peter Gunn but won Sinatra a prize for its cover.

Which Four Seasons member wrote the music for Sinatra's 1970 album Watertown?

Bob Gaudio, who wrote Four Seasons hits such as 'Sherry', composed it with lyricist Jake Holmes; for the first time in his career, Sinatra added his vocals to orchestral tracks that were already recorded.

How did Sinatra's mother Dolly die in January 1977?

A plane crash on Mount San Gorgonio killed her on January 6, 1977, as she flew to see him perform in Las Vegas; he cancelled his shows to mourn.

Which 1971 movie role did Sinatra give up because of trouble with his hand?

Harry Callahan went to Clint Eastwood after Sinatra withdrew; his last major film role came in 1980, as a New York homicide cop opposite Faye Dunaway in The First Deadly Sin.

Which Fox sitcom took a 1955 Sinatra hit single as its opening theme?

Married... with Children opened every week with Love and Marriage, a song Sinatra had introduced in a 1955 television production of Our Town.

Sinatra gave which film star a Maltese dog called Maf, short for Mafia Honey?

Marilyn Monroe dated Sinatra for several months in 1961, and the dog's imagined memoirs later became a prize-winning novel by Andrew O'Hagan.

In Anchors Aweigh (1945), Sinatra's co-star Gene Kelly dances with which animated character?

Jerry Mouse stepped in after MGM failed to get its first choice, Mickey Mouse, from Disney, and the sequence became the film's most famous number.

Which fellow crooner founded the Frank Sinatra School of the Arts, a public high school in Queens, New York?

Tony Bennett founded the school in 2001 with his wife, Susan Benedetto, and it now sits in Astoria near the Kaufman Astoria film studios.

In which 1955 film musical does Sinatra play Nathan Detroit, a gambler running an illegal craps game?

Guys and Dolls handed Sinatra a part that Sam Levene had created on Broadway, even though director Joseph L. Mankiewicz wanted Levene.

Which Italian star joined Sinatra and Cary Grant in the 1957 war epic The Pride and the Passion?

Sophia Loren played the Spanish woman both men compete for, and Cary Grant pursued a real romance with her during the shoot in Spain.

Which actress starred opposite Sinatra in Young at Heart, the 1954 film named after his hit song?

Doris Day and Sinatra also shared the soundtrack album, and the title song that named the film was hailed as his comeback single.

Sinatra's father, Marty, came from the town of Lercara Friddi on which Italian island?

Sicily was his father's birthplace, while his mother, Dolly, came from a village near Genoa, at the opposite end of Italy.

Which song, the last Sinatra sang in public, supplied the words on his original grave marker?

The Best Is Yet to Come closed his final public performance in February 1995, and its title stayed on his gravestone until the stone was replaced more than twenty years later.

Sinatra's fourth and final wife, Barbara, had previously been the wife of which Marx Brother?

Zeppo was Sinatra's neighbour in Rancho Mirage; Barbara divorced him in 1973 and married the singer three years later.

Which bandleader's orchestra backed Sinatra on the 1966 live album recorded in the Copa Room at the Sands?

Count Basie and his band had already made two studio albums with Sinatra, in 1962 and 1964, before the Las Vegas shows were taped.

Which producer made Sinatra's final solo studio album, L.A. Is My Lady, in 1984?

Quincy Jones co-wrote the title track, and its video drew cameos from Michael Jackson, Jane Fonda and Donna Summer.

Which record label, Sinatra's home as a solo artist since 1943, dropped the fading star in 1952?

Columbia let him go at the low point of his slump; the following March he signed a seven-year contract with Capitol and began his comeback.

In which 1965 war film does Sinatra's American colonel lead Allied prisoners across Italy toward neutral Switzerland?

Von Ryan's Express has the prisoners hijack a freight train for their getaway, and it became one of Sinatra's biggest box-office successes.

Which 1957 musical cast Sinatra as a womanising nightclub singer opposite both Rita Hayworth and Kim Novak?

Pal Joey won Sinatra a Golden Globe, and he gave Rita Hayworth top billing because she had long been the studio's biggest star.

Which songwriting team, also behind the musical Cabaret, wrote the theme from New York, New York that Sinatra adopted?

Kander and Ebb wrote it quickly and in anger after Robert De Niro rejected their first attempt at a title song as too weak.

Which folk group first recorded It Was a Very Good Year, four years before Sinatra's Grammy-winning version?

The Kingston Trio's Bob Shane needed a solo number for the 1961 album Goin' Places, so composer Ervin Drake wrote the song for him.

Which lyricist teamed with Jimmy Van Heusen to write Come Fly with Me and All the Way for Sinatra?

Sammy Cahn won Oscars for three songs that Sinatra introduced on screen, the first of them Three Coins in the Fountain.

Which CBS private-eye series gave Sinatra a rare television guest role in an episode aired in February 1987?

Magnum, P.I. paired him with Tom Selleck in an episode shot that January, his first TV drama since Contract on Cherry Street a decade earlier.

The Grammy-winning cover painting of Frank Sinatra Sings for Only the Lonely shows Sinatra made up as what?

A clown in the sullen style of the opera Pagliacci stares out from the sleeve, painted by Nicholas Volpe, and the cover won a Grammy at the very first ceremony.

Sinatra's 1980 concert, then the largest paid audience on record for a solo performer, filled which football stadium?

Maracanã in Rio de Janeiro drew a crowd estimated at 175,000 to hear him in January 1980.

Which jazz singer, whose 52nd Street club performances the young Sinatra watched, became a lasting influence on him?

Billie Holiday and the cabaret singer Mabel Mercer were two of his chief models, Mercer for showing him that a song has to tell a story.

Which actress, Sinatra's co-star in Some Came Running and Can-Can, became an honorary member of the Rat Pack?

Shirley MacLaine earned her first Oscar nomination for Some Came Running and later made a cameo in the Rat Pack's Ocean's 11.

Which Cold War leader visited the Hollywood set of Sinatra's musical Can-Can in 1959 and was reportedly shocked?

Nikita Khrushchev met the cast on the set that day, and Sinatra served as master of ceremonies at the studio luncheon held for him.

Sinatra's 1945 short film The House I Live In, which earned an honorary Oscar, was made to oppose what?

Antisemitism is tackled head-on when Sinatra, playing himself, stops a gang of boys chasing a Jewish child and talks them round.

Unable to get a ringside seat for the 1971 Ali–Frazier fight, Sinatra got in by working as what?

A photographer for Life magazine was his way in to the Fight of the Century, the first bout between two unbeaten heavyweight champions.

Which Las Vegas entertainer first recorded Summer Wind for the American market, a year before Sinatra's hit version?

Wayne Newton made it the title track of a 1965 album; the tune had begun that same year as a German song called Der Sommerwind.

At which Las Vegas hotel did a slumping Sinatra make his debut in the city in September 1951?

Desert Inn crowds were thin, with Sinatra singing to half-filled houses after Hollywood had turned its back on him.

Which Monday Night Football commentator was the announcer for Sinatra's 1974 television concert, The Main Event?

Howard Cosell announced the ABC special from Madison Square Garden, and the concert was later released as the album The Main Event – Live.

Which 2019 film ends its final scene on Sinatra's recording of That's Life?

Joker sets its closing moments to the 1966 single, and Sinatra's recording returned five years later in the sequel, Folie à Deux.

Which hard-rock singer covered Sinatra's That's Life on his 1986 solo debut album, Eat 'Em and Smile?

David Lee Roth, newly out of Van Halen, made it a minor hit at the end of 1986 with a video that MTV played in heavy rotation.

Which singer recorded Sinatra's hit That's Life in 1967, on the album that followed her Atlantic breakthrough?

Aretha Franklin made the album Aretha Arrives soon after shattering her elbow on tour, and played one track's keyboard part with her left hand only.

Which pop star sang That's Life, the song Sinatra made famous, on her 2024 album Harlequin?

Lady Gaga called Harlequin a companion album to a film musical in which she also performs the song on screen.

Sinatra's album That's Life includes Somewhere My Love, the vocal version of Lara's Theme from which David Lean epic?

Doctor Zhivago composer Maurice Jarre wrote the melody, and Paul Francis Webster added the words that turned it into a pop song.

Sinatra's 1966 album That's Life includes The Impossible Dream, a song written for which Broadway musical?

Man of La Mancha had opened on Broadway only the year before, with its star Richard Kiley the first to sing the number.

Sinatra's That's Life peaked at number four on the Hot 100 but spent three weeks atop which other Billboard chart?

Easy Listening had the single at number one across December 1966 and January 1967, at a time when rock acts dominated the main chart.

Which singer, later famous for Little Green Apples, made the version of That's Life that Sinatra heard in his car?

O.C. Smith had sold well in Detroit and Los Angeles, but his single was only released nationally after Sinatra's cover climbed the charts.

Sinatra's 1966 album That's Life includes his cover of which New Vaudeville Band novelty hit?

Winchester Cathedral reached number one in America that year with a vocalist singing through cupped hands to mimic an old megaphone crooner.

Which 1993 film, Robert De Niro's debut as a director, uses Sinatra's recording of That's Life on its soundtrack?

A Bronx Tale grew out of Chazz Palminteri's one-man play, and it pairs the track with a second Sinatra recording, Same Old Song and Dance.

Many players on Sinatra's That's Life session belonged to which famed collective of studio musicians?

The Wrecking Crew only got that name later, popularised by the memoir of drummer Hal Blaine, who played on the session himself.