Is Frank Sinatra your favorite crooner? Take the quiz!

By: Carolyn Brooks Fleming
Image: The Movie DB

About This Quiz

Frank Sinatra is one of the most famous entertainers of all time. With his one-of-a-kind voice and cooler than cool style, "Old Blue Eyes" did things his way and set the standard for generations to come. Take the quiz and see what you know about this legend!

Which famous crooner inspired Sinatra to become a singer?

Sinatra saw Bing Crosby perform in the 1930s.

Why did Sinatra go out of his way to avoid eating alone?

Sinatra was an only child who spent a lot of time alone. His mother was a midwife who dabbled in politics. His father was a boxer and a fireman.

Sinatra won a Supporting Actor Oscar for his role in which film?

Sinatra won an Oscar for his role in 1953's "From Here to Eternity," it was his first non-singing role.

Who were Sinatra's wives, in chronological order?

Sinatra was married to Nancy Barbato, Ava Gardner, Mia Farrow, and Barbara Blakely. All three of his children - Nancy, Frank Jr., and Christina, were born to his first wife.

In September 1935, Sinatra performed on a radio program, "Major Bowes' Original Amateur Hour," as part of what vocal group?

The Hoboken Four were known as the Three Flashes before Sinatra joined them. Sinatra and his group won the Major Bowes radio talent show, beginning his rise to fame.

What is the name of the record label Sinatra founded in 1961?

Reprise, founded by Sinatra, was purchased in 1963 by Warner Bros. Sinatra became a vice president for the label.

Sinatra first visited the White House while campaigning for which U.S. president?

Sinatra first visited the White House while campaigning for Franklin D. Roosevelt. He supported the election of FDR to an unprecedented fourth term in office.

Sinatra employed an older woman to accompany him on tour, specifically to carry a satchel stocked with what?

Sinatra reportedy owned about sixty quality hairpieces.

Which famous New York restaurant once opened on Thanksgiving, just to please Frank Sinatra?

Patsy's was one of Sinatra's favorite restaurants, and he had his own table upstairs. One year, Sinatra made plans to dine there on Thanksgiving. The restaurant owner didn't want Sinatra to know they usually closed for that holiday, so he invited employees and their families to eat there that day, to fill the tables and make everything seem normal.

Although Sinatra and certain celebrity friends were known publicly as the Rat Pack, what other name did they privately use?

The name "the Summit" was inspired by a 1960 summit in Paris, attended by world leaders. "The Rat Pack" was a name coined by actress Lauren Bacall.

Regarding Sinatra's alleged mob connections, who said, "I'm not suggesting he didn't know them, I'm just saying he didn't drive the getaway car."

Tina Sinatra made this comment during an interview after her father's death. She is a daughter of Frank Sinatra and Nancy Barbato.

What musical instrument did Sinatra learn to play, after receiving it from his uncle as a gift?

Sinatra played the ukulele and sang along while walking the streets, in his early years.

When baby Frank was born, he was blue and not breathing, thought to be dead. Who brought him back to life?

The birth was problematic because baby Frank weighed 13 1/2 pounds and his mother was small. The baby was pulled out with forceps and set aside on a kitchen counter - not breathing - while the doctor attended to Mrs. Sinatra. Frank's grandmother picked him up and held him under cold water to make him cry.

In 1957, how did Sinatra describe rock music?

Sinatra described rock as being "brutal, ugly, degenerate" and more, in an article he wrote for a French magazine. However, in later years he covered songes by Simon & Garfunkel, Stevie Wonder, Kris Kristofferson, the Beatles, and more.

The Rat Pack included Sinatra and which other Las Vegas regulars?

Dean Martin, Sammy Davis, Jr., Peter Lawford, and Joey Bishop often performed onstage in Vegas while drinking, smoking, and telling impromptu jokes.

What is the title of the duet Sinatra recorded with his daughter, Nancy?

Studio executives were reluctant to release "Something Stupid." They worried that the public would be scandalized by a father and daughter singing a love song.

Why did Sinatra try to avoid being photographed on his left side?

Sinatra was injured at birth on the left side of his head, as a result of a birth by forceps, and did not like to have his scars photographed.

Why did President John F. Kennedy cancel a planned visit to Sinatra's house?

JFK cut ties with Sinatra due to rumors of mob connections. Soon after, Sinatra switched allegiances from the Democratic Party to the Republicans. He supported the campaigns of Richard Nixon and Ronald Reagan.

When Sinatra and wife Ava Gardner fought, what did she toss out of a 14th-floor window?

Sinatra's assistant, Tony Consiglio, a friend from school days, spent hours hunting for Ava Gardner's ring on the street and sidewalk below. He eventually found it.

Songwriter Paul Anka wrote English lyrics for a French song, creating what Sinatra standard?

Anka wrote new lyrics, unrelated to the original French song, "Comme d'habitude." Where the English lyric is "my way," the original French was "as usual."

What is Artanis?

Artanis was Sinatra's film production company, which produced "None but the Brave" and "The First Deadly Sin." By the way, Artanis is Sinatra spelled backwards.

One of Sinatra's wives, Barbara Blakely, was the ex-wife of which celebrity?

Barbara Blakely was once married to Zeppo Marx, the youngest of the comedic Marx Brothers. Zeppo's real first name was Herbert.

Actress Mia Farrow once revealed that Sinatra might be the father of her son, Ronan, who was born during her marriage to whom?

Woody Allen has acknowledged that Ronan Farrow, originally named Satchel Ronan O'Sullivan Farrow, could be the biological son of Frank Sinatra.

For what project did Sinatra receive a special Academy Award?

"The House I Live In" was a short film, meant to promote racial and religious tolerance during World War II.

What food did Sinatra reportedly keep stocked on his private plane, so he could avoid strange foreign cuisine?

Sinatra ate his franks and beans cold, straight from the can.

Which U.S. president awarded the Presidential Medal of Freedom to Sinatra?

President Reagan said giving this award made it "fun to be president" and that Sinatra "truly did it his way."

What extra bit of lyric did Sinatra add to his famous song, "New York, New York"?

Lyricist Fred Ebb did not appreciate Sinatra's insertion of the phrase, "A-number-one."

Which of these artists appeared on Sinatra's 1993 album, "Duets"?

Aretha Franklin, Luther Vandross, Liza Minelli, and Bono were among the artists who appeared on "Duets." The album was criticized by some critics because none of these artists recorded in the studio with Sinatra; some recorded their parts over a special digital telephone line! Liza Minelli phoned it in from Brazil.

At the time of his death, Sinatra's FBI dossier had how many pages?

His dossier had 1,275 pages, mostly available to the public today. Sinatra was a man of interest to the FBI, both for his possible connections with organized and for his involvement with the Communist Party.

Sinatra was known as Ol' Blue Eyes and also as the Chairman of what?

Some say a DJ coined the term "Chairman of the Board." Others say he got the title after founding his record company.

In what year did Sinatra perform in concert for the last time?

Sinatra's final concert took place in 1995, at the Palm Desert Marriott Ballroom in California.

What is the epitaph on Sinatra's tombstone?

Sinatra's tombstone reads, "The best is yet to come." That's the title of the last song he ever performed in public. He died on May 14, 1998, at the age of 82.

Sinatra made his feature film debut in which 1941 movie?

Sinatra's film debut, in "Las Vegas Nights," was uncredited. He sang "I'll Never Smile Again" with the Tommy Dorsey Orchestra.

What crime was Sinatra accused of, by gossip columnist Walter Winchell?

In 1944, Winchell anonymously reported to the FBI that Sinatra was dodging the draft. The charge was unfounded - Sinatra was exempted due to a perforated eardrum.

The lyric, "And now, the end is near, and so I face the final curtain," is from which Sinatra classic?

The lyric is from "My Way."In the UK, "My Way" stayed in the Top 40 for 75 weeks. After Sinatra's death, his daughter, Tina, said that he did not like that song.

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