Oscars Writer Wins $50 Bet Over Controversial Drake Joke

During the 2025 Oscars, Conan O’Brien delivered a controversial joke about Kendrick Lamar calling Drake a 'pedophile,' which drew mixed reactions from audiences. The joke, crafted by writer Skyler Higley, referenced a recent feud between the two rappers and Lamar's Super Bowl Halftime Show performance of his diss track 'Not Like Us.' Higley revealed on X that he had bet $50 with the show’s executive producer that the joke would be well-received, ultimately winning the wager. While some fans appreciated the humor, others criticized it as inappropriate, especially given Hollywood's history with similar allegations. The joke's approval by the Academy's Standards and Practices team allowed it to air without edits, showcasing a notable moment in the ceremony. This incident comes amidst ongoing legal disputes between Drake and Universal Music Group regarding the promotion of Lamar's track, which Drake claims defames him.