Conan O’Brien Needs A Friend

Staff Review With Skyler Higley

March 12, 2026

Key Takeaways Copied to clipboard!

  • Staff writer Skyler Higley joined Conan O'Brien on *Conan O'Brien Needs A Friend* to discuss his comedic origin, which was heavily influenced by the accessibility of comedy content online and the example set by Conan's own career struggles documented in *Conan O'Brien Can't Stop*. 
  • Higley's hiring in 2020 occurred during the pandemic, and his initial remote setup in Chicago gave Conan the impression he was being held captive due to the low ceiling in his apartment. 
  • The success of Higley's joke about Kendrick Lamar and Drake at the previous year's Oscars demonstrated the power of perfectly timed comedy and immediately elevated his standing with Conan. 

Segments

Staff Writer Introduction
Copied to clipboard!
(00:00:13)
  • Key Takeaway: Conan O’Brien is interviewing his Oscar writing team members one-by-one, starting with Skyler Higley, as a special segment.
  • Summary: Conan is temporarily pausing his usual fan segment to interview members of his writing team who worked on the Oscars. He describes his routine of dramatically entering their workspace to interact with them. Today’s guest is staff writer Skyler Higley, whom Conan intends to learn more about.
Oscars Joke Success
Copied to clipboard!
(00:04:23)
  • Key Takeaway: A specific joke Higley wrote for the Oscars regarding Kendrick Lamar and Drake received an overwhelmingly positive, almost curative, reaction from the live audience.
  • Summary: The joke involved referencing the Super Bowl halftime show and suggesting Kendrick Lamar should call Drake a pedophile midway through the Oscars. Conan described the audience reaction as so powerful it could cure ailments. This moment marked a turning point where Conan began to respect Higley as a person.
Comedic Origin Story
Copied to clipboard!
(00:06:05)
  • Key Takeaway: Higley’s decision to pursue comedy was solidified in junior high/high school due to the rise of comedy podcasts and the influence of specific TV shows like 30 Rock and Community.
  • Summary: Higley felt isolated as a child and found comedy provided a salve for anxiety, citing Conan’s documentary Conan O’Brien Can’t Stop as influential. He dropped out of college after one year to move to Chicago to pursue sketch and improv comedy, feeling it was a viable career path in the 2010s era.
Early Writing & Getting Hired
Copied to clipboard!
(00:12:49)
  • Key Takeaway: Higley secured his writing job after submitting a packet to Conan O’Brien Needs A Friend that included a deliberately shocking pitch: ‘Conan O’Brien does blackface.’
  • Summary: After moving to Chicago and working terrible jobs, including a brief stint in a pyramid scheme, Higley began contributing to ClickHole, earning $15 for his first published headline. He was hired after a packet he submitted a year prior was revisited during COVID-19 hiring needs, where his confidence and unique comedic voice stood out.
Oscars Takeaways and Process
Copied to clipboard!
(00:21:21)
  • Key Takeaway: Working on the Oscars demonstrated that despite the massive scale and celebrity presence, the core comedy writing process—idea generation, fighting over jokes, and last-minute adjustments—remains fundamentally the same as smaller shows.
  • Summary: Higley noted the surreal experience of being surrounded by celebrities and the immediate, massive public reaction to every joke delivered live. However, he observed that the adrenaline-fueled process of finalizing material in the days leading up to the show was identical to working on smaller projects, proving the consistency of the creative workflow.