The writer behind Conan O’Brien’s controversial joke about Kendrick Lamar calling Drake a "pedophile" during the 2025 Oscars revealed he made a $50 bet with the show’s executive producer that the joke would land well with the audience.
During the live broadcast, O’Brien quipped, "We’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile," adding, "Don’t worry, I’m lawyered up."Comedian Skyler Higley took to X (formerly Twitter) to confirm his involvement, writing, "Wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. Just made $50." In a follow-up post, he thanked the Academy and the Standards and Practices team for allowing the joke to air without cuts, acknowledging that the humor passed the network’s review process.
The joke was a reference to Lamar’s recent Super Bowl Halftime Show performance, during which he performed his diss track "Not Like Us," aimed at Drake. In the song, Lamar calls out Drake, and the rapper has since filed a lawsuit against Universal Music Group (UMG) over the promotion of the track. Drake accuses UMG of using illegal tactics to boost the song's success and harm his brand amid ongoing contract negotiations. UMG has tried to delay the lawsuit’s proceedings and claimed that Drake’s legal team is preparing to drop some allegations, a claim Drake's attorney has denied.
In other Oscars news, Anora had a major night, winning Best Picture, while director Sean Baker took home several awards. Actress Mikey Madison won Best Actress, and other films like The Brutalist, Wicked, and Conclave also saw recognition.
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