But after decades as host of the Late Show, Letterman was never insecure about his age… until recently.
"If I was 38, I'd probably still be wanting to do the show," Letterman told the New York Times this week. "When Jay [Leno] was on, I felt like Jay and I are contemporaries. Every time he would get a show at 11:30, he would succeed smartly. And so I thought, This is still viable — an older guy in a suit. And then he left, and I suddenly was surrounded by the Jimmys."
"The Jimmys" are Jimmy Fallon and Jimmy Kimmel, the new stars of late night. And in less than a month, Letterman will end his run as the Late Show host, to be replaced by former Comedy Central star, Stephen Colbert.
Letterman denies that the Jimmys pushed him out of his job, though, even as they made him more aware of his age. He also says it was his own decision to retire and the network didn't push him out, even though he wasn't included in talks to decide who his replacement would be.
"Just as a courtesy, maybe somebody would say, 'You know, we're kicking around some names. Do you have any thoughts here?' But it doesn't bother me now," Letterman shared. "At the time, I had made the decision [to leave] and I thought, OK, this is what comes when you make this decision."
And after more than 33 years in television, Letterman still wonders if he's actually ready to let his career go.
"I'm awash in melancholia," he said. "Every big change in my life was full of trepidation. When I left Indiana and moved to California. When Regina and I decided to have a baby — enormous anxiety and trepidation. Those are the two biggest things in my life, and they worked out beyond my wildest dreams. I'm pretending the same thing will happen now."
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