It was supposed to be a fun night out with Jon Stewart and Pete Davidson at the New York Knicks game, but it turned out to be the beginning of an existential crisis for the man who once helmed The Daily Show.
Friends of Stewart report the 60-year-old comedian up until this point was happy with being an elder statesman of comedy. From his humble beginnings as a stand-up joke slinger, Stewart was catapulted into the limelight by transforming Comedy Central’s The Daily Show and is now enjoying heading The Problem with Jon Stewart on Apple TV+. There’s even talk of CNN giving him the 9-11 PM block for a talk show that focuses on politics through a comedic lens.
Despite a lifetime of achievement, Stewart realized it didn’t matter once he saw that Saturday Night Live alumni Pete Davidson had shaved his head.
The paparazzi flocked to Davidson and hundreds — maybe thousands — of photos were taken. They asked all sorts of questions about why he did it. Was it because he was dating a hot new model? Someone even asked who the old dude sitting next to him.
That someone was Jon Stewart.
What made it all worse was that Davidson was sporting dark sunglasses, too. How could Stewart compete with that?
“You know, I interviewed George Carlin,” Stewart told a photojournalist who was fixated on Davidson’s easy breezy smile. And what did he get in return? “OK, boomer.”
Sources say Stewart put on a brave face and was able to make it to the end of the game. Once he got home he rewatched the time he won The Mark Twain Prize for Humor. “Yeah, I still got it,” he thought to himself. “I totally crush the New York Times crossword puzzle. Can Pete do that? Probably not because he’s too busy dating supermodels, smoking weed, and not being Jon Stewart.”
Mental health experts believe Stewart should be OK in a few days. Actor and funnyman Ben Stiller suffered something similar when he went to see the Knicks with Davidson, and friends say he’s mostly doing fine. “If this sort of thing keeps happening, then we’re going to have to start a support group,” said one anonymous therapist.
Comedian Bill Burr went on the record to say he is never going to sit next to Davidson ever. “I like my masculinity too much to risk it,” he said.
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