Happy Birthday, Frank Sinatra: Relive the Iconic Singer’s Best Moments

by Josh Lanier
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Frank Sinatra led an impressive life. Today would have been Sinatra’s 105th birthday. Though he died in 1998 at 82 years old after suffering a heart attack, he packed a lot into his years.

The Chairman of the Board was a successful singer, movie star, movie mogul, a friend of presidents and kings, and created a celebrity so large few have come close to reaching the same heights. The fact that Willie Nelson is planning on making a tribute album to him speaks volumes to his importance to the music world.

Here are some of the more interesting moments from his life.

The Civil Rights Icon

Frank Sinatra wouldn’t necessarily be called “woke” today by many, but he was far ahead of his time on civil rights. The classic crooner financially supported Martin Luther King Jr., the New York Daily News reports, performing a benefit show for King at Carnegie Hall in 1961. He refused to play clubs that wouldn’t allow blacks to attend. Some even believe his career dip in the 1940s was because of his liberal-for-the-time views.

He credits his mother, a community organizer and Italian American activist in Hoboken, N.J., with teaching him about racism and racial justice.

But in 1945, nearly 20 years before the Civil Rights Act would be signed into law by President Lyndon Johnson, Sinatra took matters into his own hands. The New York Daily News recounts an incident where white students in Gary, Indiana, walked out of their high school to protest racial integration. Sinatra, angry about the protest, flew to Gary and spoke with the white students at Froebel High about racism and told them to “knock it off, kids.”

The students ended their boycott soon after, it was reported.

Frank Sinatra is Saved by an Audience Member

Comedian Tom Dreesen opened for Sinatra for years. He told fellow comic Kevin Nealon about a night Sinatra nearly quit singing, but an audience member saved his career, according to The Hollywood Reporter.

“There’s like 20,000 people in the arena, and I did my thing and it was a good audience,” Dreesen told the Saturday Night Live alum. “He went out and did three songs. He was rolling. And then he got on the fourth song and he totally blanked on the lyrics. The orchestra was down in the pit and they kept playing, not knowing that he was lost. And he started whispering into the microphone, ‘I’m sorry. I’m so sorry. I’m sorry.'”

Dreesen said was preparing to go back on stage and help Sinatra make as graceful an exit as he could. But then something happened.

“He turned around. There was dead silence. He had tears in his eyes. And he looked like he was going to come and lay the microphone down,” Dreesen detailed. “And a guy way up at the top of the audience stood up by himself, and he hollered out, ‘That’s all right, Frank! It’s all right because we love you!’ And he started to applaud. And the guy next to him started to applaud, and then hundreds of people started to applaud and then thousands. Pretty soon, the whole arena was cheering and cheering.”

Sinatra snapped back into focus, Dreesen said, and went into a perfect rendition of “Mack the Knife” after that. Dreesen credits the fan with saving the final years of Sinatra’s career, something Sinatra held dear.

“And he sang for two years after that. That fan brought him from the ashes that night.”

Arrested for ‘Seduction’

Sinatra is proud of his relationship history. He boasted about it often. He was married four times during his life, and he was romantically linked to a number of movie stars also.

But one of the odder moments from that history was when he was charged with “seduction” in 1938. He was having an affair with a married woman, the New York Daily News reported. The FBI was watching the mob, which Sinatra has always been linked to, so they had a file on the young man.

Police eventually brought him in on the charge because, according to the police report, he had “sexual intercourse with the said complainant, who was then and there a single female of good repute.”

Police eventually changed the charge to adultery once they realized the woman was married. But officials later dismissed the charges.

‘Frank Sinatra Has a Cold’

This is one of the most oblique moments of his life since he’s only partially involved. Pioneering journalist Gay Talese had hoped to write the definitive story on Frank Sinatra. One about a man getting older, surrounded by yes men but dealing with waning fame. Sinatra wanted nothing to do with it.

Talese was unable to secure a single interview with Sinatra for his profile. But he still observed the man from a distance and wrote what is considered the definitive piece on Sinatra.

Called “Frank Sinatra Has A Cold” the Esquire magazine profile is considered one of the best pieces written on Sinatra and captures a moment of his life intersecting with a changing world. It’s also the launching point for the New Journalism movement that opened the door for luminaries like Tom Wolfe and Truman Capote.

Don Rickles Pranks Frank

People who knew Frank Sinatra said few would ever dare to make fun of him. And never to his face. But classic comedian Don Rickles relished in teasing him, and Sinatra loved it too.

He told one of the more famous instances of Rickles getting the best of him on “The Tonight Show Starring Johnny Carson.”

Sinatra explains that he was having dinner at a New York restaurant when Rickles came over to him and asked for a favor. Rickles was on a date and wanted to impress the woman with his connections. Would Sinatra mind coming over and saying hello to prove that they were friends. “No problem,” Frank replied.

At the end of the meal, Sinatra went over to Rickles’ table and said “Hi, Don, nice to see you. How are you?” Rickles quickly retorted “Can’t you see I’m eating here, Frank? What are you doing?”

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