70 Fun Facts About Frank Sinatra

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

He was born in a tenement at 415 Monroe Street, the only child of Italian immigrants Dolly and Marty Sinatra.

What instrument did the teenage Sinatra receive from his uncle for his 15th birthday?

A ukulele, a gift from his uncle Domenico, was the instrument; he performed on it at family gatherings while idolizing the radio crooners of the day.

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

Major Bowes Amateur Hour gave Sinatra's quartet their break in September 1935, winning first prize and a place on a Bowes touring unit; the others let him join partly because he owned a car.

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

Harry James signed him in June 1939; their first record, 'From the Bottom of My Heart', sold no more than 8,000 copies, and Sinatra left within months for a bigger band.

Which bandleader's contract entitled him to 43% of Sinatra's lifetime earnings until a 1942 legal battle?

Tommy Dorsey, whose band Sinatra joined in 1940, held the contract; Sinatra said Dorsey and his own mother were the only two people he was ever afraid of.

Which 1940 recording gave Sinatra his first chart-topper, spending twelve weeks at No. 1?

I'll Never Smile Again, sung with the Pied Pipers, topped the very first Billboard best-sellers chart in July 1940 and held No. 1 for twelve weeks.

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

Bobby soxers, named for their rolled-down ankle socks, swooned at his December 1942 New York theatre opening, the start of what the press called 'Sinatramania'.

The 1944 'Columbus Day Riot' by 35,000 Sinatra fans erupted outside which New York venue?

The Paramount Theatre in Times Square was the scene; only 250 people left after the first show, so the crowd waiting outside could not get in.

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.

What was the title of the 1946 debut album that reached No. 1 on the Billboard chart?

The Voice of Frank Sinatra, a set of four 78s released in 1946, was his first album and topped the Billboard chart; its eight songs included 'Someone to Watch Over Me'.

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 is card dealer Frankie Machine's struggle; the performance earned Sinatra a Best Actor Oscar nomination and a BAFTA nomination.

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.

Sinatra's celebrated 1956 recording of 'I've Got You Under My Skin' reportedly took how many takes?

22 takes, reportedly, went into the Cole Porter number, which became a highlight of Songs for Swingin' Lovers! with its trombone solo by Milt Bernhart.

Sinatra's 1958 album Come Fly with Me, his first with arranger Billy May, was built on what idea?

A musical trip around the world was the concept, from 'Brazil' to 'Isle of Capri'; Sinatra hated the cover, complaining it looked like an advertisement for 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 Sinatra acquire soon after founding his own record company?

The Chairman of the Board, coined by New York disc jockey William B. Williams, fit the new label boss who signed Dean Martin and Sammy Davis Jr. to his company.

In Ocean's 11 (1960), Sinatra's Danny Ocean and his crew rob how many Las Vegas casinos at once?

Five casinos, the Sahara, the Riviera, the Desert Inn, the Sands and the Flamingo, were all hit at midnight on New Year's Eve.

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, JFK's brother-in-law, was cut dead after the 1962 Palm Springs snub; his part in Robin and the 7 Hoods went to another crooner, and Sinatra never again had a good word for 'Brother-in-Lawford'.

Which reclusive tycoon bought the Sands and drove Sinatra out of the hotel after a 1967 fight?

Howard Hughes bought the Sands in 1967; a brawl with its casino manager Carl Cohen followed, and Sinatra took his act across the Strip to Caesars Palace.

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

The Manchurian Candidate cast him as Major Bennett Marco opposite Laurence Harvey; United Artists only greenlit it after Sinatra got President Kennedy to voice his approval of the book.

Shooting a 1962 fight scene with Henry Silva, Sinatra broke what and refused to have it properly treated?

His little finger broke when he struck a table in the karate fight; the scene is an early Hollywood martial-arts sequence, and the injury bothered him for life.

When Frank Sinatra Jr. was kidnapped from Lake Tahoe in 1963, what ransom did his father pay?

$240,000 was the sum the kidnappers demanded, turning down Sinatra's offer of $1 million; the three men were caught within days and convicted in 1964.

After his son's kidnappers insisted on payphone calls, what did Sinatra carry for the rest of his 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's Palm Desert home got the president instead; Sinatra had built a heliport for the visit and reportedly attacked it with a sledgehammer afterward.

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 was his second wife; they separated in October 1953, two months after his Oscar-winning film opened, and divorced in 1957 but stayed close for life.

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

Mia Farrow, then starring in the soap Peyton Place, married him on July 19, 1966; the marriage lasted barely two years.

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 topped the Billboard Hot 100 and the UK chart in 1967, produced by Jimmy Bowen and Lee Hazlewood; it appeared on the album The World We Knew.

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

These Boots Are Made for Walkin' topped both charts in early 1966; producer Lee Hazlewood had her sing in a lower key and reinvented her image with bleached hair and Carnaby Street clothes.

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 recorded a rejected 1968 English demo of the French song that became 'My Way'?

David Bowie's shelved attempt, 'Even a Fool Learns to Love', was later reworked into a wholly original song, 'Life on Mars?', on Hunky Dory.

Sinatra recorded 'My Way' on December 30, 1968, in how many takes?

One take, on December 30, 1968, was all it reportedly needed; he later told songwriter Ervin Drake he 'detested' singing it, fearing it sounded self-aggrandizing.

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 after CBS executive Fred Silverman heard the record's 'doo-be-doo-be-doo' on a red-eye flight to a development meeting.

'Strangers in the Night' began as the film theme 'Beddy Bye' by which German composer?

Bert Kaempfert wrote the melody for the film A Man Could Get Killed; Sinatra's single topped the Billboard Hot 100 and the UK chart and won the Grammy for Record of the Year.

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

Antônio Carlos Jobim shared the billing on Francis Albert Sinatra & Antônio Carlos Jobim, which lost the Grammy for Album of the Year to Sgt. Pepper's Lonely Hearts Club Band.

Sinatra ended his 1971 'retirement' concert with which saloon song before the spotlight went dark?

Angel Eyes, the Matt Dennis and Earl Brent number he had recorded on Only the Lonely in 1958, closed the show with 'Excuse me while I disappear' as the light went out.

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

Ol' Blue Eyes Is Back was the title of both; the album reached No. 13 on Billboard, and the TV special reunited him with Gene Kelly.

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

Liza Minnelli introduced it in Scorsese's New York, New York; she teased Sinatra that his signature song had been written for her, and called him 'Uncle Frank'.

From July 1980, 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 with the Presidential Medal of Freedom in 1985?

Ronald Reagan presented the medal in May 1985; Sinatra had campaigned for him in 1980 and produced his January 1981 inaugural gala.

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?

He was 70 at the time and turned it down.

What is the only film Sinatra ever directed?

None but the Brave, an anti-war American-Japanese co-production released in 1965, was his sole directing credit; he also starred in it.

In both Anchors Aweigh (1945) and On the Town (1949), Sinatra played what alongside Gene Kelly?

A sailor on shore leave was his part in both; On the Town later ranked No. 19 on the American Film Institute's list of the best musicals.

Which 1956 MGM musical, co-starring Grace Kelly, grossed over $13 million with Sinatra in the cast?

High Society, with Grace Kelly in her last film before becoming Princess of Monaco, was among the year's top grossers; Sinatra reportedly earned $250,000 for it.

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.

Sinatra's 1960 TV special welcomed which star home from the Army, the two swapping hits?

Elvis Presley sang 'Witchcraft' while Sinatra sang 'Love Me Tender', a truce after Sinatra had called rock and roll a 'rancid smelling aphrodisiac'.

Sinatra's 1993 album Duets, his best-seller, was made with duet partners who did what?

Recorded remotely over digital phone lines: Sinatra insisted his partners not be in the studio while he sang, so their parts were sent in over fiber-optic lines from studios elsewhere.

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

Bono, who taped his part from Dublin, also introduced Sinatra when he received the Grammy Legend Award in 1994.

For Sinatra's 80th birthday in 1995, which landmark glowed blue?

A tribute show that night, Sinatra: 80 Years My Way, featured everyone from Ray Charles to Salt-N-Pepa.

In which year did Congress award Sinatra the Congressional Gold Medal?

1997 was the year; the medal was authorized on May 14, exactly a year to the day before he died.

According to his widow Barbara, what were Sinatra's final words?

He died of a heart attack at Cedars-Sinai in Los Angeles on May 14, 1998, aged 82.

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

The lights were dimmed along the Strip in tribute the night after he died, the city's classic salute to the headliner who had ruled the Sands in the Rat Pack years.

Sinatra is buried in Desert Memorial Park in which California city?

Cathedral City, next door to Palm Springs, is home to Desert Memorial Park, where he lies near his parents, buried with a bottle of Jack Daniel's and a pack of Camels.

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.

Sinatra's Palm Springs house Twin Palms, commissioned in 1947, was designed by which architect?

E. Stewart Williams designed Twin Palms, with its piano-shaped pool; Sinatra had asked for a Georgian mansion and was talked into desert modernism instead.

Roughly how much did Frank Sinatra weigh at birth, a delivery that needed forceps?

13.5 pounds was his reported birth weight; the forceps scarred his left cheek and neck and damaged his left eardrum, and his baptism was delayed until April 1916.

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.

How many votes won Sinatra's quartet first prize on the 1935 radio talent show?

40,000 votes carried the quartet to first prize; each member earned $12.50, and the prize was a six-month contract to perform on stage and radio across the US.

Which 1959 Sinatra album stayed on the Billboard pop chart for 140 weeks and won Album of the Year?

Come Dance with Me! took the Grammy for Album of the Year; Billy May's arrangements won a Grammy too, and the record peaked at No. 2 during its 140-week run.

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

Bob Gaudio wrote the music and Jake Holmes the lyrics; despite later acclaim it peaked at No. 101 and reportedly sold only about 30,000 copies at first.

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, citing a hand injury?

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.