Jon Stewart Shares David Letterman’s Wise Words About Failure

Jon Stewart may be considered late-night royalty today, but as he shares in a new behind the scenes clip from a recent Daily Show audience Q&A, his first foray into into late-night ended in ignominy

Fortunately, David Letterman was there to help put it all in perspective.

The question posed to Stewart seemed simple enough: What’s the best piece of advice you’ve ever been given? The host, however, described it as “such an end-of-life question.” After taking a moment to think, and explaining that he never really had a mentor as “I was raised feral,” he recalled a memorable exchange with Letterman during what would ultimately be the final episode of The Jon Stewart Show

In 1993, Stewart became one of MTV’s most recognizable faces when The Jon Stewart Show gained massive popularity—quickly. So quickly, in fact, that in just its second season, the 30-minute show was retooled as an hour-long syndicated series to fill the scheduling gap left by Arsenio Hall when he stepped away from his own late-night series. 

“I was the natural replacement for Arsenio,” Stewart joked. “Because I think a lot of people are like, ‘Hey—the hip, African American guy. Let’s stick a maybe small Jew in his place and see what happens.’”

After about nine months, Stewart and his show were served their walking papers—just before he walked out on the stage to host what would be his final episode, on which Letterman was a guest (back when you rarely saw one talk show host appear as a guest on a rival’s show).

“We were all very sad,” Stewart explained. “And when your name is on it, and they tell you to get out of the building, it’s very hurtful.” But Letterman had some advice for the then-up-and-comer that have stuck with Stewart. 

“On the final show, [Letterman] said to me: ‘Don’t confuse cancellation with failure,’ and I thought that was really interesting. And then, in the commercial break, he said: ‘Although, this is also a failure.’”

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