Conan O'Brien Needs a Friend: Jessica Williams

Release Date: August 18, 2025

Episode Overview

This episode features comedian, actress, and writer Jessica Williams, known for her work as the youngest correspondent on The Daily Show and her starring role in Apple TV’s Shrinking. Conan and Jessica share a naturally playful, warmly candid conversation about comedy origins, improv, acting, finding connection in showbiz, working with legends like Jon Stewart and Harrison Ford, and the everyday hilarity and humility that comes with following your creative path.

Key Discussion Points & Insights

1. Novocaine, Knock-Knock Jokes & Starting Off Loopy

• Conan recounts his fresh-from-the-dentist state, slurring words and eager to podcast while his face is still numb (02:07).
  • “If I had a drink right now, it would all come out my mouth.” (04:10, Conan)
• Warm-up includes silly knock-knock jokes, goofball wordplay, and riffing with the co-hosts and Jessica (06:16).

2. Jessica’s First “Friend” as a Guest – Stage Chemistry

• Conan describes meeting Jessica performing an event together—how immediately easy riffing felt, leading him to insist she be booked on the podcast (08:25).
• Jessica jokes about being “pressured” to declare herself Conan’s friend for the show’s premise (01:32).

3. The Cruise Ship Murder Story

• Conversation veers into a true crime tangent: co-host Sona retells being present on an Alaskan cruise where a passenger committed a murder (10:18–12:11).
  • Jessica: “It’s always the husband.” (11:13)
  • The group jokes about the morbid real-life “murder on the cruise” scenario.
  • The challenge of making light of dark stories and returning to comedy after a heavy beat (12:11).

4. Jessica Williams’ Comedy & Career Origin Story

• Jessica discusses her comedic upbringing, nurtured by her “bawdy” grandmother who introduced her to late night, Space Ghost Coast to Coast, and Adult Swim (19:22).
• First steps in improv via comedy sports and high school, Cal State Long Beach, and Upright Citizens Brigade.
  • “I do think everything’s kind of inherently interesting... I know a little bit about a lot of things.” (20:49, Jessica)

5. Wisdom, Lifelong Learning & Humility

• Both Jessica and Conan celebrate staying curious and never getting calcified in comedy or life.
  • “Wisdom is—you don’t know anything.” (21:08, Jessica)
  • “The more you learn, the less you know.” (21:13, Conan)
• Discussion on the “coolness” in comedy versus “earnestness,” and the virtue of “not knowing everything.”

6. Evolving from Improv, Early Gigs, & The Daily Show

• Jessica relives auditioning for The Daily Show out of college (13:00) after being told she wasn’t quite right for a Will Ferrell movie, and quickly finds herself surrounded by established pros.
• She highlights lessons gained at UCB, the high-pressure differences between Saturday Night Live and The Daily Show, and her need for supportiveness over harshness in bosses (28:00–29:49).
  • “I do a lot better when people are nicer to me. I don’t thrive when someone’s withholding.” (28:43, Jessica)

7. Inspiration: Julia Louis-Dreyfus, Harrison Ford, & Acting Philosophy

• Praise for Julia Louis-Dreyfus’ performance in Veep and her overall work ethic, focus, and humility (29:45–30:32).
  • “She’s always listening. That’s the kind of actor I want to be.” (30:29, Jessica)
• Conan shares admiration for legends like Harrison Ford and Martin Short who don’t get “calcified,” marvels at Ford’s on-screen “pop” from Star Wars and his lasting movie star allure (31:48–33:41).
  • Jessica recounts working with Harrison Ford (Shrinking), his power during an emotional scene, and being awestruck by her proximity to greatness (38:01–39:55).

8. Improv vs. Stand-Up and the Power of Ensemble Play

• Conan and Jessica bond over preferring improv and group-based comedy to stand-up (43:07–44:55).
  • “I like the teams. Standup is very isolated. Improv is about the group.” (44:28, Jessica)

9. Lessons from Comedy Sports & Clean Comedy

• Group recounts early experiences in clean improv settings (e.g. Comedy Sports), how “not cool” environments taught discipline, respect for the audience, and creative boundaries—no swearing, brown bag penalties, etc. (47:19–48:56).
  • “It taught me earnestness... to satire something, you have to love it.” (48:56–49:06, Jessica)

10. Carving a Creative Path, Early Struggles, and Showing Up

• Jessica presents how she strategized her early comedy career, convinced her parents to let her blend college with UCB classes, and the significance of “being around, showing up” (49:34–50:52).
  • Describes sleeping in cars between shows, taking odd jobs to subsidize pursuit of creative work.
• Conan tells an analogous story of his naive beginnings and learning by doing—infomercials, misapplied drugstore makeup, and navigating LA by Thomas Guide (50:52–52:24).

11. On Tallness, Beauty Standards, and Confidence

• Jessica discusses growing up tall, feeling different from beauty norms in media, and ultimately embracing her uniqueness—especially as a Black woman (55:33–56:18).
  • “It informed so much of who I am... as I got older, I was really happy... It made me feel equal to men I was playing against.” (57:00, Jessica)

12. Reflection on Gratitude & Enjoying the Moment

• Conan shares a family maxim: “Take what you can get and ask for more,” encouraging Jessica to relish her career milestones (40:36–41:37).

13. LEGO Fan Tribute & Listener Art

• The team marvels at a detailed LEGO recreation of the podcast studio built by a fan (61:25–65:11).
  • Fun roasting of each other’s LEGO likenesses; appreciation for creative, attentive listeners.

Notable Quotes & Memorable Moments

• Jessica Williams on childhood and curiosity:
  “I do think everything’s kind of inherently interesting and I think that I’m very curious about the way the world is... I know a little bit about a lot of things.” (20:49)

• Jessica Williams on humility:
  “Wisdom is—you don’t know anything.” (21:08)

• Conan on lifelong learning:
  “The more you learn, the less you know.” (21:13)

• Jessica on bringing earnestness to comedy:
  “I don’t like cool comedy. I like earnestness, 100%.” (47:17)

• On working with Harrison Ford:
  “He was destroying. He was absolutely destroying the scene in every way... it was like being too close to a fire.” (39:21, Jessica recounting a moment filming Shrinking)

• Conan on creative persistence:
  “Go where they’re doing the thing you love. Even if you’re just talking to some of the elves outside Santa’s workshop. Eventually, you’ll be in there.” (50:04)

Timestamps for Important Segments

• Novocaine, Conan’s dental work & knock-knock jokes: 02:07–07:29
• Jessica on feeling pressured to be Conan’s friend: 01:32
• How Conan and Jessica first connected and riffed onstage: 08:22–09:11
• Sona’s Alaska cruise ship murder story: 10:00–12:11
• Jessica’s comedy origin, her grandmother, and improv: 13:00–20:49
• On wisdom and lifelong learning: 21:08–22:40
• Comedy sports & improv vs. stand-up: 43:07–44:55
• Working with Jon Stewart & kindness in workplaces: 23:03–29:45
• Reflection on giants like Julia Louis-Dreyfus & Harrison Ford: 29:45–34:08
• Jessica’s emotional experience acting with Harrison Ford: 38:01–39:55
• Struggles and “showing up” early career stories: 49:34–52:24
• Embracing tallness and identity: 55:33–58:05
• Listener LEGO model appreciation: 61:25–66:12

Episode Tone & Vibe

• Playful, intimate, and infectiously goofy, mixing rapid-fire bits with real-life honesty.
• Deep mutual appreciation between Conan and Jessica; both value humility, curiosity, and hard-won confidence.
• Warm humor about comedy’s “uncool” roots, the quirks of a performer’s life, and the camaraderie of finding your people.

For New Listeners

This episode stands out for its palpable chemistry, deep-dish career reflection, earnest celebration of mentorship and curiosity, and genuine laugh-out-loud moments. Whether Jessica Williams is recounting her Vegas-lady grandmother’s lessons or emoting over a scene with Harrison Ford, her voice rings earnest and inviting. For Conan fans craving the “find-a-friend” spark that made the show’s best moments, this episode overdelivers.