Conan O’Brien’s Kendrick Lamar Joke At The Oscars Went Super Viral. Turns Out The Writer Who Wrote It Totally Had A Bet Going

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At the 97th Academy Awards in 2025, viewers enjoyed numerous laughs, primarily due to Conan O’Brien, the first-time host, and his side-splitting opening monologue. Previously known for his late-night reign, O’Brien made a triumphant return to live TV with a standout joke that poked fun at Drake and Kendrick Lamar’s ongoing feud, quickly becoming a viral sensation. Interestingly, one of the show’s writers was so certain the joke would be successful they even placed a wager on it!

Approximately halfway through the program, during a pause while the Oscars were being presented, host Jimmy Fallon made an aptly timed joke referencing Kendrick Lamar’s well-known Super Bowl LI half-time performance.

Conan O’Brien’s Drake Joke

At this point in the performance, it’s about time for Kendrick Lamar to make an appearance, and as tradition suggests, he might take aim at Drake with accusations of inappropriate behavior towards children (or something that implies pedophilia).

Following the popularity of his joke at the Oscars, Skyler Higley used platform X to disclose a backstage wager he had placed. Frankly, it’s tough not to admire the self-assuredness behind it.

The Drake Joke Wager

Even before the jokethe joke was planned to be displayed on the teleprompter, Higley was confident it would be well-received. So much so, he chose to place a bet on it.

As a film enthusiast, I can tell you that my joke hit the mark instantaneously inside the Dolby Theatre, igniting a blend of laughter and surprised reactions. Within mere minutes, fans and viewers were quoting and sharing it across various social media platforms. Yet, for me, the one person working behind the scenes, the success of this joke wasn’t solely about delivering a brilliant punchline; it also meant pocketing a small cash reward.

A daring decision – indeed, it proved profitable. This method surely ranks among the most gratifying means for earning $50 swiftly. The author appears to agree, expressing this thought:

“A shrewd gamble – undoubtedly, one that proved lucrative. It certainly belongs to the list of the most fulfilling ways to secure fifty dollars promptly.

Wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. Just made $50.

In comedy writing, figuring out what will make an audience laugh is a crucial aspect of the job, yet there’s usually no real stake involved. Higley, a veteran writer with experience on shows like CONAN and @midnight, was certain he had a hit on his hands. The wager adds an additional dimension of humor to the situation – it’s one thing to compose a joke for millions to hear, but it’s another level entirely to be so convinced of its impact that you’re prepared to risk money on it.

Ever since his Super Bowl halftime performance, Lamar has been under the spotlight, especially following his bold jab at Drake. In “Not Like Us,” he didn’t mince words, aiming direct shots at Drake, labeling him a “colonizer” and causing a stir with a line that sparked conversation online: “Attempting to strike a chord, it’s probably A minor.” However, one of the most pointed moments occurred when he slightly altered a particularly biting lyric. Rather than saying “Certified Lover Boy? Certified pedophiles” in full, he intentionally left out the last word, referring to Drake’s 2021 album titled Certified Lover Boy.

When Conan O’Brien cracked that joke at the Oscars, it wasn’t just a clever quip; it was also a subtle and smart reference to one of the year’s most impactful musical events. The intelligence behind the joke can be attributed to Skyler Higley, who pocketed $50 as a result.

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2025-03-05 20:17