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Over 20 years after his death, music legend and actor Frank Sinatra remains a titan in pop culture and music history. Though he was a successful musician until the end of his life, Sinatra went through a period in the early 1950s when his career took a nosedive. While suddenly facing irrelevancy, Sinatra noticed the way that people treated him. He shared that people he thought were his friends could no longer look him in the eye.

A black and white picture of Frank Sinatra wearing a white collared shirt.
Frank Sinatra | Silver Screen Collection/Getty Images

Frank Sinatra’s career stalled in the early 1950s

After an explosive rise to success in the 1940s, the emergence of rock ‘n’ roll music dimmed Sinatra’s star power. Audiences looked to younger, newer artists, and Sinatra did not adapt to changing musical styles. His reported ties to the mob and public affair with Ava Gardner didn’t help matters either.

In the early 1950s, Sinatra lost his film contract with MGM and his record contract with Columbia. His career was practically in free fall before he made a sudden turnaround with his Oscar-winning performance in From Here to Eternity. This role reinvigorated his work, re-establishing him as a movie star and scoring him a contract with Capitol Records. 

He noticed that people treated him differently during this time

During this career slump, Sinatra noticed that not only did fans treat him differently, but those he thought were friends did too. His opening comic, Tom Dreesen, explained that this was a defining moment in the singer’s life.

“He said, ‘There was a time when I was the hottest thing in the country,’” Dreesen told the Desert Sun. “‘I could pick up the phone and any major recording company would take my call. I could call any agency, William Morris, they would take my call. I could call the president of the United States and he would take my call. Then I got cold. And for three years, I was really cold.’”

People would no longer take his calls and treated him much differently than they did when he was a major star. When Sinatra became famous again, these people were often ashamed.

“‘I’d be at a party and I’d look across the room, and there’s that guy that wouldn’t take my call,’” Sinatra told Dreesen. “‘I’d look at him and he couldn’t look me in the eye. He’d look down on the floor.’”

This taught Sinatra an important lesson about show business.

“‘What he didn’t understand was, now I understood. I couldn’t do business with him. That’s why he didn’t take my call. We’re in show business. I couldn’t do business with him. But what I understood is, it wasn’t his fault. It was mine. I thought we were friends,'” the singer told Dreesen.

Those close to Frank Sinatra said he was ‘lonely’

Sinatra righted his career and maintained fame. Despite all the success, Dreesen said the singer was still lonely, perhaps partially due to the transactional nature of friendships in show business.


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“What American artist do you know that was a star for over 60 years? This guy sold out in countries where they didn’t speak English,” he said. “There was only one Frank Sinatra. But the truth is, he was far lonelier than anybody really knew. He really was a lonely guy. It comes out in his songs because he was the poet laureate of loneliness.”