Skyler Higley, a talented writer, crafted the perfect punchline that resonated at the 2025 Oscars. During Conan O'Brien's monologue, a joke involving Kendrick Lamar and Drake not only brought laughter but also made Higley $50 richer. This quip was part of O'Brien's triumphant hosting debut at the Oscars, where he fearlessly tackled hot-button topics.
Higley had wagered with the event's executive producer that his joke would be a hit. O'Brien delivered it with his trademark humor, poking fun at publicist Karla Sofía Gascón. The joke highlighted Gascón's notoriety for past controversial comments about Islam, the Black Lives Matter movement, and diversity within the Oscars community. Her presence at the ceremony was notable after facing criticism and ostracization for her remarks.
"Little fact for you: Anora uses the F-word 479 times. That’s three more than the record set by Karla Sofía Gascón’s publicist" – Conan O'Brien
The audience received the joke well, affirming Higley's confidence in his writing prowess. O'Brien's monologue did not shy away from addressing controversies, including those surrounding Gascón. By ribbing her, he effectively acknowledged the discussions swirling around her presence while maintaining a humorous tone.
"Karla, if you’re going to tweet about the Oscars, remember, my name is Jimmy Kimmel" – Conan O'Brien
In his routine, O'Brien also referenced Drake's "Certified Lover Boy" album. Currently embroiled in a legal dispute, the album is at the heart of Drake’s lawsuit against Universal Music Group. The lawsuit accuses the record label of defamation and harassment, alleging they propagated a false narrative about Drake being a pedophile.
O'Brien's ability to humorously navigate sensitive issues without offending those involved marked his hosting as both entertaining and daring. The joke exemplified how humor could be used to address ongoing controversies in a way that resonated with audiences.
