‘Prove It!’ Episode 5: Colbert Writer Delivers a Slam-Dunk Finale

After six months and five official attempts at dunking, The Late Show with Stephen Colbert’s Asher Perlman delivered a slam-dunk finale—metaphorically speaking.

Colbert first put his writer to the test back in January, after Perlman vowed that he could learn how to pull off a double clutch dunk in midair with a two-handed reverse finish, a la Ja Morant, within six months.

Perlman had so far come up short, but yesterday’s Late Show brought viewers the grand finale of “Prove It!”, the segment designed to hold Perlman’s feet to the fire.

After recapping his training progress and evolving medical maladies for Colbert, Perlman reflected on the past six months.

“You went into this with an enormous amount of hubris,” Colbert noted. “Did you learn anything about yourself?”

“Here’s what I learned,” Perlman explained. “I didn’t accomplish my goal, but having that goal was still worthwhile.”

He went on to trace that sentiment back to the song “The Impossible Dream” from Man of La Mancha, explaining the song’s message is that “Having a dream, even if it’s doomed, is still a noble thing.”

With that, Perlman launched into his own rendition of the song. 

“We don’t have time for this,” Colbert said. “We have a hard commercial break.”

But Perlman powered through, tearing away his suit to reveal a Late Show jersey as The Late Show Band kicked in to accompany him. Perlman grabbed a basketball and stood in front of the hoop that has loomed over him for his four past installments of “Prove It”—but this time he didn’t dunk. Three stagehands lifted Perlman up to the hoop, allowing him to drop the ball behind his back and into the hoop behind while he serenaded the audience of his quest “to reach the unreachable star.”

“He can’t dunk,” Colbert concluded. “But if it helps, you also can’t sing.”

“Give me six months,” Perlman replied.

As Perlman revealed in an interview before the stunt, his quest to dunk wasn’t a total loss. After his second attempt at a dunk earlier this year, Perlman revealed, Late Show guest Robert De Niro shook his hand to acknowledge the attempt.

“De Niro shook your hand. You’re a made man,” Colbert pointed out.

“I’m untouchable,” said Perlman.

Asher Perlman has been a staff writer for The Late Show since 2019, amassing six Emmy nominations and four WGA nominations (including one win) for his work on the show. While this appears to be the end of his ‘Prove It’ segments on The Late Show, he’s got tons of other work for fans to enjoy. Also a cartoonist for The New Yorker, Perlman published his first cartoon collection, Well, This Is Me, last year. He has another, Hi, It’s Me Again, due out this September, and he just launched a newsletter via Substack.

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