Frank Sinatra’s Friend Shared the Fastest Way to Bore Ol’ Blue Eyes

Though Frank Sinatra gave surprisingly few interviews for someone with as much star power as he had, his friends have filled in some gaps about the life of the musician. His longtime friend and opening act Tom Dreesen once shared some of Sinatra’s major pet peeves in conversation. Bringing up a certain topic would cause the singer to abruptly quit a conversation.

Frank Sinatra became close friends with his opening comedian

Sinatra discovered Dreesen’s comic act during a show for Sammy Davis Jr. They became fast friends, and Dreesen soon began traveling with Sinatra as his opening act.

“I shined shoes in taverns,” Dreesen told the Desert Times. “I sold newspapers on the corner to feed my brothers and sisters. I paid a lot of life-long dues that really grounded me when I first started becoming well-known as a stand-up comedian. I think that’s what my appeal was to Frank. The way I grew up, he knew that.”

Dreesen said he always knew that no matter what he accomplished, his obituary would describe him as Sinatra’s opening act. He once expressed this feeling to the singer.

“‘Maybe my obituary will say, ‘The singer who toured with Tom Dreesen,’” Sinatra responded. “We both started laughing like two high school kids. It was just so funny the way he said it.”

His friend shared the fastest way to make the singer leave a conversation 

Following years of working together, Dreesen had a good idea of what Sinatra was like. Though the musician had a temper, Dreesen recounts times where he displayed radical generosity. He was signing an autograph for a woman’s husband because he was at home sick. When she complimented Sinatra’s cufflinks, he gave them to her.

“They were $2,000 cuff links. I know where he got them,” Dreesen later explained. “He said, ‘Thank you.’ And he signed the autograph and took the cuff links off and handed them to her. He said, ‘Give these to him.’ She said, ‘No, no, no, no, no! I don’t want them, I was just admiring them.’ He said, ‘No. I want you to give those to your husband.’”

According to Dreesen, Sinatra had little interest in money and possessions. 

“Frank Sinatra did not care about money,” Dreesen said. “You want to bore him? You want him to walk away? Start telling him how much money you have and all the things you own. He’d turn around and walk away.”

Frank Sinatra never wanted to be controlled by his possessions 

Dreesen once explained that part of Sinatra’s distaste for money and physical possessions stemmed from the fact that he did not want his things to control him. He shared this philosophy with Dreesen soon after giving away the cufflinks.

“He said, ‘Tommy, if you possess something that you can’t give away, then you don’t possess it. It possesses you.’ He once said to me, ‘Nothing you possess is yours. The second you die, it transfers. It belongs to someone else. We’re only using it.’”