‘Happy Days’ Star Henry Winkler Remembers Wild Story From Time Hanging Out With Frank Sinatra

by Taylor Cunningham

When Happy Days star Henry Winkler was an angsty teenager, he idolized Frank Sinatra. Lucky for him, when he grew up and became a star, he was able to meet the singer in person—twice. And as it turned out, Sinatra was a fan in return.

While chatting on the phone with Vulture’s Devon Ivie, the 76-year-old classic TV icon admitted that he used to relax to the smooth sounds of the rat pack crooner when he was younger. In fact, his memories of spending nights with Sinatra on his record player are vivid to this day.

“When I was 15, I smoked regular Kent cigarettes,” he admitted. “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 windows so my parents wouldn’t smell it, feeling very dramatic.”

Once Henry Winkler graduated from Yale and became a breakout star as The Fonz, he earned a celebrity status that rivaled the 11-time Grammy winner. So because Winkler still loved his music, he grabbed his best friend and co-star Ron Howard and headed to Vegas while Sinatra was doing a residency. And, of course, Sinatra happily agreed to a meet and greet.

“There was a group of about six of us,” Winkler shared. “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. He would make fun of Rona Barrett, who at that time was a gossip columnist. And he made fun of her mercilessly.”

The ‘Happy Days’ Star Spent The Statue of Liberty Bicentennial with Frank Sinatra

The second time that Henry Winkler met Frank Sinatra was in 1976 when the U.S. was celebrating the bicentennial of the Statue of Liberty.

As Winkler remembered, the singer was in a tent with “every single bottle of liquor you could imagine.” And he was having one of his legendary, rowdy good times.

“You had to provide all those bottles of liquor for him, depending on his taste,” he continued. ” 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.”

And while Winkler admitted that most people would ridicule another for acting so frivolously, that kind of behavior was normal for Sinatra. And furthermore, those sorts of antics were exactly what made people love him so much.

“He could pull that off,” Winkler admitted.