How Larry King Scored an Impossible Interview with Illusive Frank Sinatra Thanks to Jackie Gleason

Angela AndaloroWed, June 3, 2026 at 9:12 PM UTC

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Larry King and Frank SinatraCredit: CNN/YouTube -

When Larry King Live premiered on CNN on June 3, 1985, the esteemed host, who died in 2021, had no idea he'd be sitting across from famous figures for over three decades

The radio host and journalist first connected with singer Frank Sinatra in the mid-1960s, with the help of a comedian friend

In an interview, King explained how those events led him to conduct Sinatra's final major broadcast interview in 1988, a decade before the singer's death

Larry King's unusual introduction to Frank Sinatra led him to be part of the singer's personal history.

In a series of interviews conducted from late 2009 to early 2010, the late journalist spoke with the Television Academy in a look back on his career. Among the many stories he told was the one of how he ended up getting to interview the musical legend for the first time, on his radio show in the mid-1960s.

"I'd say Frank Sinatra was the number one star in the world. I'd say Frank Sinatra was Michael Jackson and Elvis Presley, rolled into one. In the 1960s, you couldn't get bigger," he shared, setting the scene.

Sinatra was everywhere, but King pointed out he "avoided the press."

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Asked at a dinner party what would be impossible in his profession, King replied, "Frank Sinatra, on my radio show for three hours, during the time he's in Miami."

"And Jackie Gleason said, 'You got him.' I said, 'What?'... He said, 'Next Monday, you got him.' "

King warned that he was going to plug the appearance and Gleason continued to insist that Sinatra would show up. King doubled back after unanswered messages out to Sinatra's team, and when the station shared they'd be taking out an ad in the Miami Herald for the interview. Once again, Gleason doubled down.

"He got mad. He's like, 'Didn't I tell you he was coming?' I said, 'Okay Jackie, I'm sorry.'

At five minutes to 9 o'clock that Monday, Sinatra still hadn't appeared at the station.

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"The whole radio station stayed. The people who work during the day did not go home — secretaries, anybody, salesmen — just to be in Frank Sinatra's presence. It was unbelievable," he recalled.

"You couldn't be bigger. I'm standing, it's five to nine, I go on at five after nine... Suddenly, this limo comes. Frank gets out. His PR guy comes with him."

They quickly get set up and begin the interview, which King begins by asking, 'Why are you here?' Because the audience has got to wonder how I got him. I don't know how I got him."

Sinatra tells the story of a night when he was performing in New York City and got laryngitis on his closing night. He called Gleason and asked if he could take over his hour slot. The entertainer came through for him.

Frank Sinatra and Jackie GleasonCredit: Bettmann Archive/Getty

"I walked him out to his limo. When he was leaving, I leaned in, I said, 'Jackie, I owe you one.' Then I check into town to sing here at the Fontainebleau, and I get a message to call Gleason," Sinatra said.

"I call up. He answers the phone, I said, 'Jackie, it's Frank,' and all he said was, 'Frank, this is the one.' "

King explained that from there, he developed a rapport with Sinatra, which led him to do what ended up being his last television appearance, on Larry King Live in May 1988.

During the interview, Sinatra talked about undergoing surgery after an intestinal infection, lightheartedly joking about how close he was to death. He was thankful at the time that the surgery was making him feel better. King asked the singer if he was scared at how bad things had gotten.

"Of course, I was frightened. I said to my surgeon, 'How serious is this?' He said, 'It's serious, Frank. I'm not going to tell you it's removing a tooth out of your mouth. We have to put you together very, very carefully when we're finished... It was a 7½ hour operation and when I came out of it, there were smiles and everyone was smiling. I said, 'I guess we won?' and he said, 'We sure did... You'll never have another problem.' "

Sinatra would spend the final years of his life managing different health issues. The singer died a decade after the interview, after suffering a heart attack at his home in Los Angeles.

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Source: “AOL Entertainment”