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Skyler Higley is one of the newest up-and-coming comedians and writers in the Chicago comedy industry, according to Laugh Factory. In addition, he has written for After Midnight, Conan, and The Onion.
On March 3, Skyler Higley, who penned jokes for the Oscars, posted the following tweet on X:
"wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. just made $50."
Kendrick Lamar recently performed his famous Drake diss track, Not Like Us, during the halftime show at Super Bowl LIX. Additionally, he also got Drake's ex, Serena Williams, to perform on the song, which added to the ongoing feud.
At the 97th Academy Awards, the host, Conan O'Brien, took a dig at the ongoing feud between Drake and Kendrick Lamar by saying:
"Well, we're halfway through the show, which means it's time for Kendrick Lamar to come out and call Drake a p*dophile."
This was a reference to the Super Bowl LIX Halftime show. Not Like Us was released in May 2024. After the increased popularity of the diss track, Drake's team took legal action in a Manhattan court in November 2024, accusing UMG, the label that manages Kendrick Lamar and Drake, of unfairly increasing the diss track's popularity.
Conan O'Brien added another statement regarding the court filing by adding:
"Don't worry. I'm laweryed up."
When Conan delivered the joke, it received a strong reaction from the people, proving Higley right. Ultimately, he won the $50 bet made with the executive producer.
Who is Skyler Higley?
Skyler Higley is a stand-up comedian and a TV writer who has also been featured on multiple YouTube comedy videos. After making the journey from Salt Lake City, Utah, Skyler found a home in the Chicago comedy scene and pursued his dream of becoming a stand-up comedian.
Skyler Higley has also worked as a staff writer on After Midnight, hosted by Taylor Tomlinson. The 2025 Oscars was his first time writing for an award show. Skyler Higley was one of the 18 writers for the 2025 Oscars, held on March 3.
However, this is not the first time that Higley is working with Conan, as both have worked together in the TV series Conan in the past. The talk show was hosted by Andy Richter and Conan O'Brien.
Laugh Factory, a comedy club chain in the U.S., describes Higley as:
"a comedian, writer, and one of the youngest rising stars of the Chicago comedy scene."
Higley and Laugh Factory have collaborated on a range of videos, added to the Laugh Factory's YouTube channel. They further describe his achievement by adding:
"Skyler is a co-producer of the Young Hustle Show, the dopest young show in Chicago comedy. He has produced comedy shows at Annoyance Theater, Second City, and all across Chicago. He can be found as a regular performer at Zanies, shows at the Laugh Factory, and many local independent shows in Chicago."
One of Skyler Higley's old tweets has also been featured on billboards during Twitter's inspirational campaign. As of now, he is working as a stand-up comedian and staff writer on the After Midnight Show.
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