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Henry Winkler had his celebrity-making role in Happy Days, a show during the same decades in which Frank Sinatra re-established himself as a powerhouse in music. Winkler said he often listened to Sinatra when he was growing up. Winkler had the opportunity to meet the celebrity once he rose to fame himself. He explained that they got along, but he did witness some of Sinatra’s late-night antics. The actor watched the singer cut a hole through his tent in order to better watch a celebration. 

Frank Sinatra wears a tuxedo and stands in front of a microphone. Henry Winkler wears a tuxedo at the Golden Globes red carpet.
Frank Sinatra and Henry Winkler | Martin Mills/Getty Images; Frazer Harrison/Getty Images

Henry Winkler said he often listened to Frank Sinatra growing up

Winkler grew up as Sinatra was rising to unprecedented levels of success. He said that he often listened to the singer as a teenager.

“That’s the stuff,” he told Vulture in 2022. “When I was 15, I smoked regular Kent cigarettes; they were so small you could hardly see them. I listened to Frank Sinatra in the wee hours of the morning, blowing the smoke out through the window so my parents wouldn’t smell it, feeling very dramatic.”

Henry Winkler watched Frank Sinatra slice a hole in his tent

Years later, Winkler met Sinatra at one of his concerts.

“I met him twice. He was everything I expected,” Winkler explained. “I took Ron Howard with me to Las Vegas to see him perform; there was a group of about six of us. We went backstage and he was very happy to meet me because he liked Happy Days. I introduced him to my friends and then we went back to see him after the show. He remembered every single name.”

The second time Winkler met Sinatra was at an anniversary celebration for the Statue of Liberty.

“He’s in a tent and has every single bottle of liquor you could imagine,” Winkler explained. “You had to provide all those bottles of liquor for him, depending on his taste.”

The tent, apparently, wasn’t to Sinatra’s taste, as it blocked the view of the celebration. Sinatra took care of the problem his way.

“He couldn’t see the festivities, so he took his steak knife, stood up, walked over to the wall of the rented tent, and cut himself a picture window. Not just a window but an entire wall of windows so he could see what was happening,” Winkler said. “He could pull that off.”

Frank Sinatra had a reputation for being a bit destructive 

Sinatra’s attack on the tent was by no means the first time the singer damaged something. Per WGNO, Sinatra once threw a golf club at one of the chandeliers at the Sahara casino in Las Vegas. While it didn’t shatter, he did leave a dent in the expensive light fixture. 

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Frank Sinatra and John Wayne Nearly Came to Blows Over Sinatra ‘Crony’ JFK and Communism

When John F. Kennedy went back on his decision to stay with the singer, Sinatra smashed up a helipad that he had built for the president. He also kicked in the door of the presidential suite. 

Sinatra could even be destructive when he thought he was doing a good deed. After a party guest accidentally broke one of his ex-wife’s favorite alabaster birds, Sinatra smashed the second bird to make her feel better.