Staff Review With Skyler Higley - Conan O’Brien Needs A Friend Recap

Podcast: Conan O’Brien Needs A Friend

Published: 2026-03-12

Duration: 30 min

Guests: Skyler Higley

Summary

Skyler Higley, writer for Conan and the Oscars, reflects on his journey from Utah to comedy writing in Chicago, his early influences, and the creative dynamics of working on high-pressure projects like the Oscars.

What Happened

Skyler Higley joins the show as Conan pulls back the curtain on his writing team's dynamic. Skyler recounts his start in comedy, growing up in Salt Lake City, Utah, in a religious environment, and how comedy became a gateway to understanding the world beyond his upbringing. Comedy, particularly through shows like '30 Rock,' 'Parks and Recreation,' and 'Community,' inspired him to pursue writing. He described dropping out of college to move to Chicago to immerse himself in the comedy scene, working odd jobs and eventually contributing to Clickhole and The Onion.

Skyler shares the surreal experience of being hired to write for Conan during the pandemic. He describes the unique writing process for the show, including pitching ideas and navigating the challenges of remote collaboration. One of his standout contributions was pitching a Christmas-themed show during August of 2020, which Conan enthusiastically embraced, leading to a memorable production.

Conan and Skyler also reminisce about working on the Oscars, with Skyler highlighting the enormous scale and pressure of the event. He recalls the adrenaline of last-minute changes and the surreal experience of witnessing iconic celebrities up-close. Skyler reflects on the joy and camaraderie of working in a writer's room, emphasizing that comedic collaboration thrives in supportive, fun environments.

The episode also dives into the role of comedic instincts and the importance of finding one's voice in writing. Skyler discusses the balance between crafting jokes for a large-scale live event like the Oscars and keeping the process enjoyable despite the pressure.

The conversation veers into humorous anecdotes about Conan's antics in the writer's room, from his dramatic entrances to his faux-abusive joking with the team. Skyler humorously notes how these moments of levity are vital to the creative process.

Skyler and Conan touch on the evolving nature of comedy, the impact of digital platforms like YouTube and podcasts on making comedy more accessible, and how each generation of comedians builds on its predecessors. Skyler credits Conan's documentary, 'Conan O'Brien Can't Stop,' for helping him see comedy as a way to navigate personal struggles.

The episode ends with Skyler expressing gratitude for the opportunities he's had and the creative freedom to explore ideas, while Conan praises Skyler's unique comedic voice and contributions to his team.

Key Insights

• Skyler Higley dropped out of college to move to Chicago and pursue comedy, taking odd jobs until he landed gigs at Clickhole and The Onion. His path underscores how immersing yourself in the right environment often matters more than traditional education.
• When Skyler pitched a Christmas-themed show to Conan in August 2020, the absurdity of the timing didn't derail the idea—it fueled its success. This highlights how embracing unconventional timing can lead to standout creative work.
• Writing for the Oscars involves a level of pressure most don't realize: last-minute script changes and the surreal proximity to icons like Brad Pitt. The adrenaline of these moments makes it one of the most intense gigs in comedy writing.
• Conan O'Brien's faux-abusive joking with his team, like dramatic entrances and over-the-top antics, isn't just for laughs—it keeps the writer's room energized. Levity in high-pressure creative spaces isn't optional; it's fuel.

Key Questions Answered

How did Skyler Higley start his comedy career?

Skyler grew up in a religious household in Salt Lake City, Utah, and found inspiration in shows like '30 Rock' and 'Parks and Recreation.' He dropped out of college to move to Chicago, where he worked odd jobs while contributing to Clickhole and The Onion, eventually landing a writing role with Conan during the pandemic.

What was Skyler Higley's experience working on the Oscars?

Skyler described the Oscars as a surreal, high-pressure environment with an enormous scale. He noted the adrenaline of making last-minute changes and the surrealness of seeing iconic celebrities up-close, while emphasizing the importance of collaboration and maintaining a fun writers' room dynamic.

What is Conan O'Brien's approach to fostering creativity in his writers' room?

Conan balances high energy and humor with fostering a collaborative, supportive environment. Skyler noted that Conan's antics, like dramatic entrances and over-the-top jokes, keep the mood light and creativity flowing even under pressure.