That’s Life: 20 Facts About Frank Sinatra You Didn’t Know

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Frank Sinatra in a scene from 1960’s Can-Can (Photo courtesy of 20th Century Fox)

Francis Albert Sinatra passed away on May 14, 1998. During his 82 years on Earth, he was one of the best-selling music artists of all time. In addition, he left an enormous imprint on pop culture via his success in film, radio, television and entertainment. Here are 20 quick facts about Ol’ Blue Eyes.

One of Sinatra’s earliest musical stints was as a member of the Hoboken Four, who passed an audition to appear on the Major Bowes Amateur Hour radio show. They each earned $12.50 for the appearance and won first prize—a six-month contract to perform on stage and radio across the United States.

The Hoboken native was hired in June 1939 by band leader Harry James, who signed Sinatra to a two-year contract of $75 a week.

Sinatra made his film debut in 1941’s Las Vegas Nights, singing “I’ll Never Smile Again” in an uncredited sequence with Tommy Dorsey’s Pied Pipers.

In a 1943 Down Beat poll, Sinatra beat out Bing Crosby, Perry Como, Bob Eberly and Dick Haymes.

During one 1940s Columbia Records recording session, Sinatra cut “Sweet Lorraine” with the Metronome All-Stars, a group that featured an array of legendary jazz musicians including Coleman Hawkins, Harry Carney, Charlie Shavers and Nat King Cole on piano.

Sinatra’s first attempt at owning his label was a failed attempt to purchase Verve Records from founder Norman Granz.

While Bing Crosby was an early influence, Sinatra later believed that Tony Bennett was “the best singer in the business.”

Frank Sinatra founded Reprise Records in 1960 as a way to allow him more artistic freedom for his recordings. He garnered the nickname “The Chairman of the Board” and even after selling the imprint off to Warner Brothers in 1968, he retained a 20 percent ownership stake in the imprint.

On Sept. 21, 1983, Sinatra filed a $2 million court case against Kitty Kelley, suing for punitive damages, before her unofficial biography, His Way, was even published.

Frank Sinatra (center) making his uncredited film debut in 1941’s Las Vegas Nights

Sinatra moved on from Harry James and signed a deal to front the Tommy Dorsey band for $125 a week at Chicago’s Palmer House.

In July 1964, Sinatra was present for the dedication of the Frank Sinatra International Youth Center for Arab and Jewish children in Nazareth.

In 1958, Frank Sinatra was one of the 10 biggest box office draws in the United States.

In the 1948 presidential election, Sinatra actively campaigned for President Harry S. Truman. In 1952 and 1956, he also campaigned for Adlai Stevenson.

Sinatra was the recipient of 11 Grammy Awards, including the Grammy Trustees Award, Grammy Legend Award and the Grammy Lifetime Achievement Award.

On Jan. 27, 1961, Sinatra played a benefit show at Carnegie Hall for Martin Luther King, Jr. and led his fellow Rat Pack members and Reprise label mates in boycotting hotels and casinos that refused entry to black patrons and performers.

Sinatra sang for the very last time on Feb. 25, 1995, before a live audience of 1,200 select guests at the Palm Desert Marriott Ballroom, on the closing night of the Frank Sinatra Desert Classic golf tournament. “The Best is Yet to Come” was the last song he sang.

In 1979, Sinatra performed in front of the Egyptian pyramids for Anwar Sadat, raising more than $500,000 for Sadat’s wife’s charities.

Sinatra was slated to play Detective Harry Callahan in 1971’s Dirty Harry, but had to turn the role down due to developing Dupuytren’s contracture in his hand.

Sinatra was honored at the Kennedy Center Honors in 1983, was awarded the Presidential Medal of Freedom by Ronald Reagan in 1985 and the Congressional Gold Medal in 1997.

In 1960, Sinatra starred opposite Shirley MacLaine, Maurice Chevalier and Louis Jourdan in Can-Can. He earned $200,000 and 25 percent of the profits for the performance.

Check out more from LIW‘s Frank Sinatra theme issue:

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