Conan O'Brien Needs a Friend
Conan Conducts A Staff Review With Writer Skyler Higley | Conan O'Brien Needs A Friend
Episode Summary
AI-generated · Apr 2026AI-generated summary — may contain inaccuracies. Not a substitute for the full episode or professional advice.
Conan O'Brien sits down with one of his Oscar writing team members, Skyler Higley, to delve into Higley’s unique origin story in comedy and his experiences working for O’Brien, particularly on the Oscars. O'Brien, usually prone to cartoonish insults, begins by expressing genuine admiration for his writing staff, setting a warm, albeit self-aware, tone for the conversation.
Higley shares his journey, beginning with his upbringing in a sheltered Mormon community in Salt Lake City, where comedy became a crucial window to the outside world. He describes the 2010s comedy boom—fueled by podcasts, YouTube, and shows like “30 Rock” and “Community”—as a formative period that made comedy feel like a viable career path. This inspiration was solidified by watching O’Brien’s documentary, “Conan O’Brien Can’t Stop,” which showed him that humor could be a “salve” for anxiety. Higley recounts dropping out of college to move to Chicago, enduring “terrible jobs,” including a brief stint in a pyramid scheme, before contributing to Clickhole.
The conversation illuminates the inner workings of Conan’s writer’s room, from O’Brien’s performative “drug raid” entrances to the essential role of “bullshitting” and tangents in fostering creativity, even if the direct output doesn't always make it to air. Higley details how he landed the job, submitting a writing packet that included deliberately provocative ideas, like “Conan O’Brien does blackface,” to stand out. He vividly recalls the monumental impact of writing O'Brien’s viral “Kendrick to come out and call Drake a pedophile” joke for the Oscars, and how the immediate, live audience reaction felt like a powerful, even curative, force. Higley reflects on the surprising “scale” and “star power” of the Oscars, noting how the process, despite its magnitude, remained fundamentally similar to smaller comedic endeavors.
Listeners will gain a behind-the-scenes look into the life of a modern comedy writer, the unique dynamics of Conan O’Brien’s creative environment, and the fascinating blend of personal journey, generational influences, and professional craft that shapes successful comedy in the digital age.
👤 Who Should Listen
- Aspiring comedy writers seeking career insights into late-night and awards show comedy.
- Fans of 'Conan O’Brien Needs a Friend' interested in the show's behind-the-scenes dynamics and the lives of its creative staff.
- Anyone curious about the creative process behind major awards show comedy and the intense environment of live televised events.
- Individuals navigating unconventional career paths in creative industries, especially those who dropped out of college to pursue their passion.
- Comedy enthusiasts interested in how generational shifts, like the rise of podcasts and YouTube, have impacted comedic inspiration and career opportunities.
🔑 Key Takeaways
- 1.Conan O'Brien's Oscar writing team, including Skyler Higley, is highly valued, despite Conan's performative 'over-the-top insults' and 'cartoonish disappointment' in the writer's room (01:01).
- 2.Skyler Higley's comedy origin story began in a sheltered Salt Lake City upbringing, where comedy served as a window into the wider world and helped him navigate anxiety (06:05, 10:09).
- 3.The 2010s comedy boom, fueled by podcasts and YouTube, alongside shows like '30 Rock,' 'Community,' and 'Parks and Rec,' normalized comedy as a viable career path for Skyler Higley's generation (06:05, 09:07).
- 4.Landing a writing job with Conan involved submitting a unique packet, including a deliberately provocative idea like 'Conan O’Brien does blackface,' to catch attention amidst many submissions (16:16).
- 5.The 'bullshitting' and seemingly off-topic tangents in a comedy writer's room are essential for fostering a creative, fun environment, even if the direct output doesn't make it to the final show (21:27).
- 6.Working on a high-profile event like the Oscars, though scaled immensely, involves the same fundamental creative process of pitching and refining jokes as smaller shows (26:34).
- 7.The immediate, live audience reaction to a successful joke, such as Conan's 'Kendrick to come out and call Drake a pedophile' line at the Oscars, can be profoundly gratifying and even 'cancer free' (05:05).
💡 Key Concepts Explained
The Conan Language
This concept refers to the specific comedic style and tone of Conan O'Brien's shows, which a writer must learn to 'speak' to successfully contribute. Skyler Higley explains that adapting his individual comedic voice to fit Conan's world, despite their differences, allowed him to produce 'the best stuff' and integrate his unique perspective into the show's established humor (19:22).
⚡ Actionable Takeaways
- →Develop a distinct comedic voice early, as Conan notes, 'sometimes you'll read a whole packet and think, 'Yeah, not one of these quite has my voice, but this is a really funny person'' (18:21).
- →Seek out environments where you 'laugh really hard' and feel supported in your creative work, as a fun writer's room significantly impacts job satisfaction (22:29).
- →Embrace unconventional or provocative ideas in your portfolio to stand out, as Skyler Higley did with his 'Conan O’Brien does blackface' pitch (16:16).
- →Recognize that even seemingly unproductive 'bullshitting' in a creative setting serves an essential purpose in fostering camaraderie and idea generation (21:27).
- →Commit to being funny to navigate difficult periods, as Skyler found watching 'Conan O’Brien Can’t Stop' showed 'you can go through things and you can be okay' (07:06).
⏱ Timeline Breakdown
💬 Notable Quotes
“"Well, we're halfway through the show, so it's time for Kendrick to come out and call Drake a pedophile."”
“"If you have a disease, if you have cancer in your body and you walk out and tell a joke like that to a room that big and you get that reaction, you will be cancer free. It cures me of any ailment I might have had."”
“"Sometimes you don't even think, 'Oh, okay. Here it is. Idea number seven, we could use that. And idea number nine, we could use that. That could go into the show. So, hire this person.' Sometimes you'll read a whole packet and think, 'Yeah, not one of these quite has my voice, but this is a really funny person.'"”
“"You can be from two very different worlds, but sort of the idiosyncrasies of I think comedy for comedy's sake and whatever this idea of like a if there is a true like north in comedy of just like funny that is like kind of all the same a little bit."”
More from this guest
Skyler Higley
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