Elmo Makes Jon Stewart a Wildly Indecent Proposal

Elmo’s Monday night visit to The Daily Show was brought to you by the letters N-S-F-W.

Jon Stewart’s unofficial version of the Sesame Street character returned to the Daily Show desk Monday, where a Knicks-related gambling problem led him to make Stewart a wildly indecent proposal.

The bit began with Stewart taking issue with the real Elmo’s recent attempt at NBA neutrality. After the puppet’s official x.com account posted that he hoped both teams would “have fun,” Knicks fans—Stewart famously among them—responded with the kind of civic grace and restraint for which New York is known.

“Are you [bleep] kidding me, Elmo?” Stewart said Monday.

Stewart then welcomed The Daily Show’s own Elmo—voiced and puppeteered by Stewart himself—to explain his side of the controversy. As it turned out, the puppet’s problem wasn’t that he lacked loyalty to the Knicks. It was that he had a rooting interest in something much more specific.

“Elmo loves the Knicks and Elmo loves the Spurs,” he said. “Elmo wants both teams to have fun, try their hardest, and Elmo just wants them both to hit the over.”

From there, Elmo’s backstory got considerably darker. He explained that he’d been banned from the betting apps and had turned instead to a bookie named Big Ricky, who lived in “a part of Sesame Street Elmo had never been to before.” Things had apparently not gone well.

“Elmo can’t count that high,” he said when Stewart asked how much he owed. “But Big Ricky can.”

Stewart tried to stage something resembling a gambling intervention, telling Elmo he was on a bad path and needed help.

The desperate puppet soon found a new angle. Upon learning that Stewart planned to attend that night’s Knicks game with his son, Elmo noted that Polymarket seemed to believe the same thing. Which meant there was money to be made if Stewart suddenly didn’t show.

Stewart was unmoved.

“I’m sorry, Elmo, no [bleep] way!” he said. “I’m taking my son. We wouldn’t miss this for anything in the world.”

That’s when Elmo made his offer.

“Please, Mr. Jon! Elmo can’t go back to the streets!” he pleaded. “Elmo will do anything, Mr. Jon! Anything!”

Elmo then punctuated the word “anything” with a hand-and-mouth gesture that made abundantly clear just how far he was willing to go to get Stewart to skip the game.

“Jesus, Elmo,” Stewart said. “You’re embarrassing yourself!”

Rejected, Elmo turned on him.

“You’re not better than Elmo!” he shouted. “Elmo will remember this! Elmo will haunt your [bleep] dreams! [Bleep] you, Stewart!”

The nearly eight-minute-long segment was the latest chapter in Stewart’s long history with—and as—the red Muppet. Last year, after Elmo’s official social media accounts were hacked and used to post racist and antisemitic messages, Stewart staged another split-screen interview to interrogate the character about his apparent sudden turn toward the manosphere and alt-right.

Longtime Daily Show viewers may also remember Gitmo, Stewart’s recurring Elmo-like hand puppet from his earlier years on the show. Complete with a tiny beard, Gitmo was used to satirize the treatment of prisoners at Guantanamo Bay, and like Monday’s Elmo, was voiced and puppeteered by Stewart.

Stewart has also shared the screen with the real Elmo. In the 1998 PBS special Elmopalooza, he appeared alongside the actual Sesame Street character as part of the show’s 30th anniversary celebration, only to be trapped in a dressing room after Elmo accidentally locked the door.

Watch the full segment at the top of this post.

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