Jimmy Fallon has played Charades dozens of times on The Tonight Show, but it’s never gone quite this bad.
Monday’s Tonight Show saw the host lead a 12-minute installment of the game—about double its usual duration—that went mostly scoreless as guests Pete Davidson and Paris Hilton most unsuccessfully put their mime skills to the test. Davidson paired up with The Roots’ Tariq Trotter for the showdown, while Fallon partnered with Hilton. By the end, however, they would all go down together.
The game went awry fast with a pair of unfortunate clues drawn at random. As the first player up, Fallon’s selected clue was “Schitt’s Creek,” forcing the host to hesitantly squat and stumble through a visual reference to dog poop that left Hilton confused. (“I got too embarrassed!” he told her afterward.)
From there, the game doubled down on double entendres. Trotter, up next, immediately laughed when he saw his clue: “Moby Dick.” His strategy? Repeatedly point to his crotch.
“What?” Davidson responded through laughter.
After miming an ocean, Trotter reverted to the obvious, extending his arm outward from his groin as Davidson again failed to guess correctly.
“That was unairable!” Fallon told his band member. “[Moby Dick]’s about a whale! You don’t do a whale?!”
After Hilton failed to mime “U Can’t Touch This” for Fallon, Davidson drew “Doctor Who,” prompting him to criticize the game’s writers.
“You guys gotta get ones from, like, today,” Davidson told the host.
Though Davidson came close to getting a correct guess out of Trotter, they came up short. Trotter agreed the clue was too dated, alleging Doctor Who was “from the ‘50s.” (Doctor Who debuted in 1963, and aired new episodes as recently as last May.)
“The score remains 0 to 0,” Fallon reminded everyone. “This is epic, epic, worst we’ve ever done.”
After that, Davidson’s wish came true: a pair of more modern clues. Fallon failed to make Hilton guess “Marty Supreme,” but Trotter and Davidson managed to put the first point on the board with “Frankenstein.”
With the duo leading 1-0, and more than eight minutes in, Fallon announced a joint round to end the contest, in which Davidson and Hilton would mime one shared clue at the same time for 10,000 points. “The heat is on,” Fallon promised, throwing in an obscure Saturday Night Live reference for good measure.
“The H is O,” he quipped—a nod to “The H is O,” one of the first SNL Digital Shorts by Adam McKay.
The grand finale clue: “Birds of a Feather.” To nobody’s surprise, nobody guessed correctly—even when Fallon insisted they blow past the 30-second timer. After over a minute of wrong guesses, Davidson gave up acting words out altogether.
“Do another word!” a frustrated Fallon shouted. “What the f*ck is going on?”
In a last-ditch effort, Davidson and Hilton drew a new clue—“One Battle After Another.” Mercifully, Fallon guessed correctly. Technically, he and Hilton won the game 10,000 to 1—but the real winners may have been the audience, who got to see a rare Tonight Show game gone wrong.
The Charades train wreck added to an already eventful Tonight Show episode, which began with newly elected New York City Mayor Zohran Mamdani crashing the monologue following weeks of Fallon referencing the mayor with a recurring joke.
