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?

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?

The group won first prize with 40,000 votes and a six-month touring contract; the others admitted they let him join because he owned a car.

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

Their first record together 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?

Sinatra called him one of only two people he was ever afraid of, the other being his mother.

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

It was his fourth chart appearance and his first on the first officially published Billboard chart.

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

'Sinatramania' broke out after his December 1942 New York theatre opening, and about 1,000 fan clubs sprang up within weeks.

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

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?

He showered constantly and changed outfits so often that the name stuck.

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

By then he was selling around 10 million records a year and performing on stage up to 45 times a week.

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

The role revived a career that had bottomed out; a year earlier he had been playing to half-empty rooms and a Hawaiian county fair.

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

He also picked up a BAFTA nomination for the same performance.

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

After their first song together Sinatra listened to the playback and 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?

Its songs of lost love and late nights are often read as a response to his collapsing second marriage, and fans called them the 'Ava Songs'.

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

The Cole Porter number became one of the highlights of Songs for Swingin' Lovers!

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

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?

He first tried to buy the declining jazz label Verve, and only started his own after that deal fell through.

Which nickname did Sinatra acquire soon after founding his own record company?

As CEO he signed fellow Rat Packers Dean Martin and Sammy Davis Jr. to the label.

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

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

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

One story has Bacall greeting the men returning 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?

His part in Robin and the 7 Hoods went to another crooner, and Sinatra 'never again had a good word' for the man he had called Brother-in-Lawford.

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

The new owner reportedly loathed Sinatra partly because he had been in love with Sinatra's second wife in the 1950s.

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

He played Major Bennett Marco opposite Laurence Harvey, and the film only got made because he agreed to star.

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

The scene is one of the earliest depictions of East Asian martial arts in a mainstream Hollywood film, and the injury bothered him for life.

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

Sinatra had offered far more, but the kidnappers declined the larger sum; the three men were caught and convicted soon after.

After his son's kidnappers insisted on payphone calls, what did Sinatra carry for the rest of his life?

He had worried during the ransom calls that he would run out of coins.

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

Sinatra had built a heliport for the visit; after the rejection he reportedly smashed it with a sledgehammer.

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

He 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?

The turbulent marriage ended in separation two months after his Oscar-winning film opened, but they remained close friends for life.

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

She left the soap Peyton Place at his urging; the marriage lasted barely two years.

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

He had cast her in his own film The Detective and, when she failed to report, 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?

It appeared on the album The World We Knew, released the same year.

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

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?

The French original is about the emotional 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?

He finished it at 5 a.m. on an IBM electric typewriter and phoned Sinatra at Caesars Palace to say he had something special.

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

His shelved attempt, 'Even a Fool Learns to Love', was later reworked into a wholly original song, 'Life on Mars?'.

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

He later told songwriter Ervin Drake he 'detested' singing it, fearing audiences would hear it as self-aggrandizing.

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

Under Gorbachev, Warsaw Pact states were being allowed to go their own way, so a spokesman reached for the song.

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

CBS executive Fred Silverman heard the record on a red-eye flight to a development meeting in 1968.

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

The single topped the Billboard Hot 100 and the UK chart and won Sinatra the Grammy for Record of the Year.

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

It was one of the best-selling albums of the year, behind only Sgt. Pepper's Lonely Hearts Club Band.

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

He had recorded the Matt Dennis and Earl Brent number on Only the Lonely in 1958.

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

The album reached No. 13 on Billboard, and the 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?

She teased Sinatra that his signature song had actually 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?

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?

Sinatra had donated $4 million to his 1980 campaign and organized his inaugural gala.

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

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?

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?

The anti-war American-Japanese co-production was released in 1965 and he also starred in it.

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

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?

It was one of the highest-grossing pictures of its year, and 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?

It became a chart hit too, lasting 17 weeks on the Hot 100.

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

The guest sang 'Witchcraft' while the host 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?

Sinatra insisted his partners not be in the studio while he sang, and one of them taped his part standing on a couch in Dublin.

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

He 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?

It was authorized on May 14, exactly one 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 casinos also stopped spinning for one minute, and record sales jumped worldwide that month.

Sinatra was buried in a blue suit and a red-and-blue tie in support of which football club?

His mother came from Genoa; he lies next to his parents in Desert Memorial Park in Cathedral City, California.

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

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?

He golfed there with Ken Venturi and swam daily; the house became a desert-modernism landmark.

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

The forceps scarred his left cheek and neck and permanently damaged his left eardrum, delaying his baptism until April 1916.

Sinatra's father Marty was a bantamweight boxer who later rose to captain in which Hoboken service?

Illiterate himself, Marty wanted his son to become a civil engineer at the Stevens Institute of Technology.

How many votes did the Hoboken Four attract to win first prize on Major Bowes' show in 1935?

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?

Billy May's arrangements won a Grammy too; the record peaked at No. 2.

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

Jake Holmes wrote the lyrics; despite critical acclaim it sold only about 30,000 copies that year and peaked at No. 101.

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

She was on her way to see him perform in Las Vegas; he cancelled two weeks of shows and recovered in Barbados.

Which 1971 movie role did Sinatra give up after developing Dupuytren's contracture in his hand?

His last major film role came in 1980, playing a troubled New York homicide cop opposite Faye Dunaway in The First Deadly Sin.