Staff Review With Skyler Higley

Summary of Staff Review With Skyler Higley

by Team Coco & Earwolf

30m•March 12, 2026
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Overview of Staff Review With Skyler Higley

This episode is a conversational staff-review segment from Conan O’Brien’s podcast (Conan O’Brien Needs a Fan), in which Conan interviews his writer Skyler Higley. They cover Skyler’s comedic origins, career path (ClickHole, The Onion, moving to Chicago), how she joined Conan’s team in 2020, and her experience writing for the Oscars. The tone is informal, anecdotal, and behind-the-scenes, with frequent banter about writers’ room culture and live show pressure. Multiple ad reads are interspersed throughout.

Key topics discussed

  • Skyler Higley’s background and how she got into comedy
  • Early influences (internet comedy, Conan documentary, sitcoms)
  • Moving from Salt Lake City to Chicago to pursue comedy
  • Early gigs: ClickHole, The Onion, odd jobs to make ends meet
  • How she landed a job with Conan (sending a packet of ideas)
  • Writing for Conan and the Oscars (notable jokes and the live scale)
  • Writers’ room culture: bullshitting, tangents, and the creative process
  • The similarities in process between small-stage comedy and large-scale televised events
  • Behind-the-scenes Oscars anecdotes (backstage “dungeon,” last-minute changes, celebrity presence)

Skyler Higley — background and career path

Early influences

  • Grew up in Salt Lake City in a religious (Mormon) environment with limited pop-culture access.
  • Found comedy via the 2010-era internet boom: YouTube, podcasts, and shows like 30 Rock, Community, and Parks and Rec.
  • The documentary Conan O’Brien Can’t Stop was formative—showed comedy as a way to cope with anxiety and personal struggles.

Career trajectory

  • Left college after one year to pursue comedy.
  • Moved to Chicago to study improv/standup and join the comedy scene (Second City, standup circuits).
  • Did odd jobs (including a short stint in a pyramid-like sales scheme) while writing and performing.
  • Wrote for ClickHole early on (appeared in one background video pouring milk down a sink).
  • Earned early credibility and pay from online pieces; remembers the significance of first paid gigs and the magic of immediate audience feedback.
  • Got noticed by Conan’s team after submitting idea packets (including intentionally provocative items to catch attention).
  • Hired during the pandemic (2020) and became part of Conan’s writers room, later contributing to the Oscars telecast.

Notable moments & anecdotes

  • Conan praises a memorable Oscars joke Skyler wrote that landed massively with the audience (the gag referenced Kendrick calling Drake a pedophile in the context of a mid-show joke). Conan jokes hyperbolically that the audience reaction cured him of any illness.
  • The writers’ room is described as a “dungeon” downstairs—where jokes are hammered out, despite Conan’s theatrical interruptions upstairs.
  • Skyler recalls the surreal scale of the Oscars: intense celebrity concentration, immediate national reaction to jokes, and the pressure that comes with live TV.
  • A last-minute idea (the “sandworm in the band”) came together minutes before the show—an example of quick pivots and spontaneity in live production.
  • Skyler taped a performer’s $20 envelope on her closet glass as a reminder of her early paying gigs.

Memorable lines / quotes

  • On the writers’ room: “You got to have the ideas, you got to fight over them… the process isn’t that much different [regardless of scale].”
  • On Conan’s live performance reaction: the audience “bathed” him in screams and laughter—Conan joked that such a reaction would cure any disease.
  • On submitting packets: including a deliberately shocking line (“Conan O’Brien does blackface”) was a tactic to make a packet memorable—used as an example of standing out (not an actual pitch).

Takeaways for aspiring comedy writers

  • Exposure matters: the internet/podcast/YouTube era made comedy feel like a viable career option—use available platforms to develop voice.
  • Be prolific and distinctive: send packets of ideas regularly; finding memorable, singular choices can help you get noticed.
  • Process matters more than scale: the creative process for a sketch in a small theater follows essentially the same steps as for a large televised event—idea testing, iterations, and rehearsal.
  • Room culture is important: playful “bullshitting” and tangents can be essential to morale and creativity, not just wasted time.
  • Be ready to pivot: last-minute changes and quick creative decisions are part of live television.

Sponsors / Ads included in the episode

Ads read during the episode include: Aruba tourism, U.S. Bank Smartly Visa, TurboTax in-person locations, Uber Teen Accounts, Miller Lite, LinkedIn Ads, SiriusXM, Alka-Seltzer Plus, and Robert Half. (These appear as host-read and produced ad segments throughout the show.)

Who should listen

  • Fans of Conan O’Brien and his behind-the-scenes process
  • Aspiring comedy writers seeking practical insight into writers’ rooms and how to get hired
  • Listeners curious about the logistics and pressure of writing for large live broadcasts (like the Oscars)
  • Anyone who enjoys informal storytelling and industry anecdotes from a mid-career comedy writer

Final note: the episode blends warm, candid storytelling with playful backstage details—valuable for both fans and anyone interested in how comedy work gets made at small and enormous scales.