Conan O'Brien's Monologue Writer Says Drake–Kendrick Joke Was a Winning Move—Literally

During the 2025 Oscars, a notable moment occurred when host Conan O’Brien, referencing the ongoing feud between rappers Kendrick Lamar and Drake, made a contentious joke. 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. Don't worry, I'm lawyered up," referencing legal threats leveled by Drake, 38, against Universal Music Group over Lamar's diss track "Not Like Us." The song, which aired during Lamar's Super Bowl performance, has fueled intense debate since its May 2024 release. This is prepared by SSP.

Skyler Higley, one of the writers for O’Brien's Oscars monologue, shared on X that he placed a $50 wager with the executive producer that his joke would resonate with the audience – a bet he won. Higley, known for his work on "Conan" and currently "After Midnight," reassured that the intention was not to take sides but to highlight the cultural significance of Drake and Lamar's feud. Higley also jokingly mentioned on X that he's calls to also write about sex abuse in the church during the show's "Conclave" segment.

Drake's fiery feud with Lamar escalated when he pursued legal action against Universal, his record label since 2009, in response to the diss track which implies he is a pedophile. To fend off such accusations, Drake cast legal proceedings not only at Universal but also at IHeartMedia. After drawn-out negotiations, a resolution was reached in late February 2025. Statements from Disney and media icons such as Rob Mills have defended the impactful nature of O’Brien’s delivery. Although the comments stirred divisions on social media, it underscored how comedy, controversy, and performance ensue during an award ceremony.

Earlier, SSP wrote that Lily Collins shared adorable family selfie from first beach day with baby daughter Tove.