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At the 2025 Oscars, Conan O’Brien dropped a witty Drake joke. This had everyone crying when the host said, “Well, we’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile”
omg this Oscars joke from Conan O’Brien
“Well, we’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile” pic.twitter.com/d7gzCFHfsF
— Spencer Althouse (@SpencerAlthouse) March 3, 2025
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The joke about Drake being a pedophile played off Kendrick Lamar’s diss track “Not Like Us.” The joke hit just after Kendrick had a massive halftime performance where he called out Drake, saying he’d probably sue if Kendrick ever performed the track. The timing of O’Brien’s joke was on point, especially with all the heat Kendrick was throwing Drake’s way. But what made it even crazier was that a producer at the Oscars was actually pushing hard for this controversial joke to air.
They believed it was going to land, no matter how risky it seemed. They were all in on the joke. Turns out, it wasn’t just O’Brien who believed in it. The punchline was written by his longtime writer, Skyler Higley, who knew exactly what he was doing.
wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. just made $50.
— Skyler Higley (@skyler_higley) March 3, 2025
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After the joke landed and the crowd reacted, Higley hopped on Twitter and let everyone know how confident he was. He tweeted, “Wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. Just made $50.” The whole thing was a gamble, but it paid off. The producers stuck their necks out for it, and with the audience laughing, Higley cashed in. Sometimes, timing and a little bit of risk lead to a perfect moment.