In 1965, Larry King was a local radio host in Miami, still trying to make a name for himself. That year, he found himself at a party at Jackie Gleason’s house. Gleason turned to the group and asked,
“What’s impossible in your profession?”
A doctor said, “We’ll never be able to make blood in a lab.” Others shared their answers. Then it was Larry’s turn.
He said, “Frank Sinatra doing my three-hour radio show.” Everyone laughed. Sinatra was the biggest name in the world—and about to open at the Eden Roc Hotel.
Jackie looked at him and asked, “What night is he dark?”
“Monday.”
“You’ve got him next Monday.”
Larry could hardly believe it—but he announced it on air that very night: Frank Sinatra, Monday at 9 p.m.
The station panicked. “Are you sure?”
“Jackie says so,” Larry answered.
Monday came. The staff stayed late. The tension was thick. At 8:58 p.m., a limo pulled up. Sinatra stepped out.
He walked in and asked, “Who’s Larry King?”
“That’s me,” Larry said.
“Let’s go.”
Larry’s first question was simple:
“Why are you here?”
Sinatra replied, “Years ago, I lost my voice before a Brooklyn show. I asked Jackie Gleason to fill in. He did an hour for me. As I walked him to his car, I said, ‘I owe you one.’ Last week, I got a message from Jackie. He said, ‘This is the one.’”
It turned into one of the greatest interviews of King’s career. Sinatra even opened up about his strained relationship with the press and the pain of his son’s kidnapping—things he’d never meant to discuss.
The two men became friends, and more interviews followed. Years later, Larry King would conduct Frank Sinatra’s final major interview in 1988.
“As a kid,” Larry once said, “I stood in line outside the Paramount just to see him. I think he was the greatest singer of my time.”
Some legends are made by talent.
Others by trust, timing… and keeping your word.
