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The 97th Academy Awards brough plenty of laughs to the 2025 TV schedule, largely thanks to first-time host Conan O’Brien and his hilarious opening monologue. The former late night mainstay returned to live TV in spectacular fashion, with one joke in particular — a sharp jab at Drake and Kendrick Lamar’s ongoing feud — became an instant viral moment. But as it turns out, one of the award show’s writers was so confident in the joke’s success that they made a bet on it.
Roughly halfway through the broadcast (which we live-blogged with reckless abandon), during a break between Oscars being handed out, O’Brien delivered a perfectly timed quip referencing Kendrick Lamar’s now-infamous Super Bowl LIX halftime show performance.
Conan O’Brien’s Drake Joke
Well, we’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile.
After the joke went viral, Oscars writer Skyler Higley took to X to share a behind-the-scenes bet he made. And honestly, it’s hard not to respect the confidence.
The Drake Joke Wager
Before the joke had even made it onto the teleprompter, Higley was so sure it would land that he decided to put money on it.
wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. just made $50.March 3, 2025
The joke landed immediately, sparking a mix of laughter and shocked reactions inside the Dolby Theatre. And within minutes, fans and viewers quoting and sharing it all over social media platforms. But for one person behind the scenes, the joke’s success wasn’t just about delivering a great punchline—it also came with a small cash prize.
A bold move—and one that paid off. That has to be one of the most satisfying ways to make a quick fifty bucks. The writer seems to think so, writing:
Wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. Just made $50.
For comedy writers, predicting what will land with an audience is part of the job, but it rarely comes with an actual wager. Higley, a seasoned writer with credits on CONAN and @midnight, clearly knew he had a winner. The bet adds an extra layer of humor to the moment—after all, it’s one thing to write a joke for millions to hear, but it’s another to be so confident in its impact that you’re willing to gamble on it.
Since Lamar’s Super Bowl halftime show, he’s been the center of attention—especially after taking such a public shot at Drake. In “Not Like Us,” Lamar didn’t hold back, firing off direct shots at Drake, including calling him a “colonizer” and dropping a line that had the internet buzzing: “Tryna strike a chord and it’s probably A minor.” But one of the most brutal moments came when he altered a particularly scathing lyric. Instead of fully delivering the line, “Certified Lover Boy? Certified pedophiles”—a reference to Drake’s 2021 album Certified Lover Boy—deliberately leaving off the last word.
When Conan O’Brien delivered that joke at the Oscars, it was not just a witty remark but a brilliant nod to one of the year’s most significant moments in music. The genius behind the joke belongs to Skyler Higley, who is now fifty dollars richer for it.