Conan O’Brien Needs A Friend

Episode: Staff Review With Skyler Higley
Date: March 12, 2026

Episode Overview

This lively episode takes a behind-the-scenes look at Conan O'Brien’s writer’s room as he sits down with staff writer Skyler Higley to discuss Skyler's comedic journey, his unconventional rise in the industry, and his contributions to Conan’s late-night and Oscar work. Amidst playful roastings, the two reflect on the craft, generational shifts in comedy, writers’ room culture, and the sometimes surreal experience of writing for the Oscars. Throughout, the tone is warm, irreverent, and packed with rapid-fire jokes and affectionate ribbing.

Key Discussion Points & Insights

Skyler’s Origin Story & Early Comedy Influences

[01:37] – [04:59]

• Conan invites Skyler to share his background, noting that while the staff spends much time together, he often doesn’t get to know writers deeply.
• Skyler jokes about Conan’s unusually respectful tone at first, expecting the usual over-the-top, theatrical ribbing Conan gives in the writers’ room.
  • "[Conan:] I kick the door open like it's a drug raid...and then I start doing cartoonish, over-the-top insults." [02:33]
  • "[Skyler:] That's what I was waiting for." [02:55]
• Skyler recaps his hiring during the pandemic (2020, amid BLM protests in Chicago)—an anxious, surreal time:
  • "Remember when we cared about BLM for a second?...then people called me up and were like, hey, do you want to meet with Conan's people?...Well, I think the world's ending, so sure." [03:50]

Zoom Beginnings and Life Underground

[04:59] – [05:25]

• Conan describes the hilariously cramped appearance of Skyler's Chicago apartment during pandemic-era Zooms, comparing it to Being John Malkovich and joking Skyler looked "held captive."
  • "[Conan:] You would appear on the screen and it looked like your ceiling was one inch above your head." [05:14]
  • "[Skyler:] It wasn't the angle. I lived underground...cheap rent when you live underground." [05:24]

The Craft: Comedy as Connection & Salve

[07:41] – [09:24]

• Skyler talks about discovering the possibility of a comedy career through the early 2010s podcast boom and platforms like YouTube.
• He credits watching Conan O’Brien Can’t Stop and Conan’s shows with normalizing anxiety and showing the therapeutic aspect of comedy:
  • "The doc...was a big deal for me as, like, a kid...if you really commit to being funny, you can make it through stuff." [08:11]
• Early influences included both stand-up (Blue Collar Comedy, Jeff Dunham) and new-era sitcoms like 30 Rock, Community, and Parks and Rec.
  • "They’re being as crazy as possible on TV and they're not happy. They're making themselves happy." [10:55]

Skyler’s Leap: From Salt Lake to Chicago

[11:44] – [14:16]

• Skyler leaves college early, moving from conservative Salt Lake City to Chicago to pursue comedy and soak up the Second City and improv scene.

  • "Comedy...kind of what got me out of being super religious...You hear about Second City...just wanted to do all of it." [12:29]

• Survival jobs: Skyler did “terrible jobs,” including a humorous stint in a pyramid scheme:

  • "[Skyler:] I was in a pyramid scheme for a couple days." [13:42]
  • Conan draws parallels between pyramid-scheme energy and his own writers’ room antics.

Breaking In: Clickhole, The Onion & Conan’s Hiring Process

[14:16] – [15:52], [21:59] – [23:35]

• Skyler starts pitching for Clickhole, earning a first $15 writing check (a pivotal moment).
  • "First time ever getting paid for writing something, like, huge." [15:47]
• When applying for Conan, Skyler notes the show’s unique “packet” process: just submit 10 ideas, no details.
  • "[Skyler:] One of my pitches was just straight up like, 'Conan O'Brien does blackface.' ...It wasn’t obviously a real pitch, but I was like, well, people are gonna remember that." [22:36]
  • Conan and Skyler both emphasize that what sets great packets apart is a clear, confident comedic voice, not just reusable material.
  • "[Conan:] 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. And that is the harder thing to find." [23:35]

Writers’ Room Culture & Why Bullshitting Matters

[27:38] – [29:58]

• Conan defends the value of chaos and goofing off in the writers’ room:
  • "I have always thought that the bullshitting in a writer’s room isn’t really just bullshitting. It’s kind of essential." [27:38]
• Skyler fully agrees, describing positive and negative writers’ room environments:
  • "[Skyler:] Other times when you’re trying to do comedy and you feel terrible and you’re under the gun and it's gotta be exactly right...it’s not fun to do." [29:33]
• Affectionate roasts continue: Conan jokes about giving Skyler a (possibly inappropriate) shoulder massage, leading to more banter about workplace boundaries.

Writing for the Oscars: Pressure & Surreal Moments

[30:08] – [34:03]

• Skyler and Conan reflect on the scale and immediacy of writing for the Oscars, from underground "dungeon" writers’ rooms to watching their jokes create headlines minutes after broadcast:

  • "Almost every joke, it felt like there was, like, a headline about, like, everybody's talking about this joke that you had just said, like, five minutes ago." [30:44]
  • "All eyes are on this. And it's live...I had not been in a space with...that many celebrities before." [31:52]

• Conan adds: the process is the same whether for 200 at Largo or millions at home—it’s about fighting for the best ideas:

  • "[Conan:] The scale can change, but the process is the same." [32:43]

• Last-minute creative chaos: The now-famous addition of "the Sandworm in the band" was a five-minutes-before-show inspiration—demonstrating the adrenaline and improvisation at this level.

Notable Quotes & Memorable Moments (with Timestamps)

• Conan on Writers’ Room Entrances:
  "I kick the door open like it’s a drug raid… and I start doing cartoonish, over-the-top insults." [02:33]

• Skyler on Getting the Job:
  "I was like, well, I think the world's ending, so sure." [03:50]

• Conan on Early Zooms:
  "Your ceiling was one inch above your head, and it looked like you were being held captive." [05:14]

• Skyler on Comedy as Therapy:
  "That documentary was...a big deal for me...I was very anxious, and you can go through things and you can be okay, and if you really commit to being funny, you can make it through stuff." [08:11]

• Skyler’s Packet Tactic:
  "One of my pitches was just straight up like, 'Conan O'Brien does blackface.' ...It wasn’t obviously a real pitch, but...what if you did it and then somebody...it’s a tactic to get people to be like, what the hell is what's going on? And then actually read it." [22:36]

• Conan on Recognizing Comedic Voice:
  "You can tell almost right away in a packet when someone knows who they are and is kind of confident about their comedic voice." [23:35]

• On Writers’ Room Bonding:
  "I have always thought that the bullshitting in a writer’s room isn’t really just bullshitting. It’s kind of essential." [27:38]
  "Other times when you’re trying to do comedy and you feel terrible and you’re under the gun...it’s not fun to do. It's weird. You can be in these situations where you’re like, this was my ‘dream job’ and I feel terrible every day." [29:33]

• On Oscar Night:
  "Almost every joke, it felt like there was, like, a headline about, like, everybody's talking about this joke that you had just said, like, five minutes ago." [30:44]

Structure & Flow

The episode is structured as a loose, organic conversation, with Conan guiding the discussion but allowing Skyler’s humor and stories to set the tone. Listeners are treated to:

• Warm, irreverent banter about inside writers’ room dynamics.
• Skyler’s candid recollections of breaking into comedy in new media’s golden age.
• Practical, real-talk about the pressures and rewards of late-night and awards show writing.
• Layered with rapid-fire jokes and affectionate “insult comedy” typical of Team Coco.
• Occasional drops of sincerity about finding one’s comedic voice and using humor to process anxiety and chaos.

Timestamps of Key Segments

• [01:37] – Beginning; introduction to staff interviews and the writers’ room atmosphere
• [03:50] – Skyler recounts his hiring during the height of COVID/blm protests
• [05:01] – Skyler’s underground apartment Zoom setups
• [08:11] – Comedy as solace, Skyler’s early influences
• [14:16] – First paid comedy writing at Clickhole
• [21:59] – Applying to Conan, writing packets, finding a comedic voice
• [27:38] – Writers’ room “bullshitting” as an essential creative process
• [30:08] – First-hand account of writing for the Oscars, live pressure
• [32:43] – The universal writing experience – process vs. scale
• [33:47] – Last-minute Oscar changes / adrenaline moments
• [34:43] – David Hopping’s luxury Oscar seat and wrap-up banter

Final Thoughts

This episode showcases the unique chemistry of the Team Coco writing staff. Skyler Higley’s personal story illustrates the democratization of comedy careers for a new generation, while the interplay with Conan highlights how much great comedy relies on collective chaos, difference, and collegial disrespect. If you’re interested in the mechanics, anxieties, and joys of comedy writing, or the transition from late night to live, high-stakes Hollywood events, this conversation pulls back the curtain with both heart and humor.