Kendrick Lamar, Drake Oscars Joke Led To ‘Dumbest Post’ Ever

Host Conan O’Brien’s Kendrick Lamar and Drake joke paid off big time at the 2025 Oscars. Not only because it was really good, but also because it made one of his writers 50 bucks.

During last night’s ceremony, the former Late Night host quipped, “We’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile.” He added, “Don’t worry, I’m lawyered up.” Conan didn’t come up with the joke, however. Comedian and writer Skyler Higley took credit for it on X, writing, “wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. just made $50.”

In a series of follow-up posts, Higley, a writer for Taylor Tomlinson’s After Midnight and a fan of good music, thanked “the academy and S&P for folding and not cutting this joke.” He was also told that “people being mad racist on this Nazi website. I’m not gonna break down how jokes work and structure to you. Unfortunately many of you are simply dumb and/or racist. I’m having a wonderful time tonight and that’s not changing!” The joke was so good, it even led to what Higley accurately described as the “dumbest post of all time.”

If Higley ever decides to retire from joke writing, he has a promising future as an illustrator!

You can see the full list of Oscar winners here.