Oscars Joke Writer Won $50 Bet Over Conan O’Brien’s Kendrick Lamar-Drake Joke: ‘I Also Wrote the “Conclave” Joke About the Catholic Church’

Conan: Rich Polk; Kendrick: Christopher Polk/Penske Media via Getty Images; Drake: Mark Blinch/Getty Images

Conan O’Brien shocked the Oscars with a joke about the ongoing beef between rappers Kendrick Lamar and Drake, and it’s one that earned the joke writer some cash. Comedian and writer Skyler Higley was the brains behind the joke, and he revealed on X during the show: “Wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. Just made $50.”

Higley, who writes for CBS’ “After Midnight” and previously worked with O’Brien on his TBS talk show “Conan,” was one of several writers who worked on the 2025 Oscars. The staff also included Amberia Allen, José Arroyo, Josh Comers, Dan Cronin, Jessie Gaskell, Berkley Johnson, Ian Karmel, Brian Kiley, Laurie Kilmartin, Carol Leifer, Jon Macks, Matt O’Brien, Agathe Panaretos and Mike Sweeney.

At the midway point of the Oscars ceremony, O’Brien walked out on stage and joked: “We’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile. Don’t worry, I’m lawyered up.”

O’Brien was referring to Lamar’s Super Bowl Halftime Show performance last month, where the rapper performed his Grammy-winning Drake diss track “Not Like Us” to much fanfare. On the song, Lamar raps: “Certified Lover Boy? Certified pedophile,” referencing Drake’s album of the same name.

“Good morning to Drake fans and also to people who like good music,” Higley wrote on X hours after the Oscars amid polarizing reactions to his joke. The writer also confronted those asking, “Why don’t you try to call out the white pedophiles?” by writing: “Well I also wrote the conclave joke about the Catholic Church try again.”

O’Brien’s “Conclave” joke alluded to sєx abuse within the Catholic Church and went like this: “The movie ‘Conclave’ is up for best picture tonight. If you haven’t seen ‘Conclave,’ its logline is, ‘A movie about the Catholic Church…but don’t worry.’”

As for the Kendrick-Drake joke, Disney executive Rob Mills told Variety he approved of the joke and explained: “When he did that in rehearsal, I was with Jeff Ross, his producer, and we were like, that joke is going to kill. And it was great! It was sort of unexpected from Conan, but that’s what made it kind of fun.”

Drake has been litigious in the fallout from the beef, filing a lawsuit against Universal Music Group. He accused the company of defamation and harassment and spreading the “false and malicious narrative” that he is a pedophile via “Not Like Us.”