Podcast Summary: Disgraceful with Grace O’Malley

Episode: Paintballs and Fancams with Michael Longfellow
Date: January 15, 2026
Host: Grace O’Malley
Guest: Michael Longfellow
Setting: New York City

Overview

This episode of DisGRACEful features comedian Michael Longfellow—best known for his time at SNL—as Grace’s auditioning co-host. With her signature irreverence and curiosity, Grace dives into Michael’s comedic roots, odd jobs, high school memories, experiences with fame and fandom, and a healthy dose of online shenanigans and running bits. Michael’s dry wit and genuine self-deprecation pairs perfectly with Grace’s playful chaos as they riff through icebreakers, fan submissions, their top films, painfully relatable anecdotes, and a Mad Libs finale.

Key Discussion Points & Insights

1. Catching Up: The Billionaire Island Gig

• [01:26] Michael recounts getting flown out to perform for billionaires on an island, under a strict NDA:

  “I got invited to an island by a bunch of billionaires to perform with a no photography or recording clause.”

• He jokes about negotiating for more pay due to the optics (“Not the least risky time for people of…well, to be inviting someone to an island to perform,” [01:53]).

2. Rapid-Fire Icebreakers & Life Anecdotes

• Therapy & Rorschach Tests:
  Neither have had Rorschachs; riff on if anyone really gets prescribed meds from “an ink blob.”
• Family & Ketamine Therapy:
  Grace’s dad experimenting with ketamine therapy, leading to funny exchanges about stealing horse tranquilizers ([02:55]):

  “He asked me if he should steal a little...so my mom could see what it feels like...”

• High School Memories:
  Michael’s alma mater pride only appeared post-grad; he quit football after a now-famous NFL player outshined him ([03:53]).

  “I quit football because we were going out for tight end together...he was younger than me and hairier and looked like a man.”

• Comedic Roots:
  Neither felt “cool” in school theater. Michael’s first real acting/audition story—driving to LA at 19 at a stranger’s invitation—was “horrifying and embarrassing” ([05:27]).

3. College, Creative Writing, and Haunting

• Arizona State Stories:
  • Michael admits to a “2.1 GPA” ([05:59]), jokes about the school’s open admissions, and forgetting his ghost-themed thesis:

    “It was an etiquette guide on how to haunt appropriately.” ([06:47])

  • Grace: “That could be a movie…prim and proper ghosts.”
• Transition to Comedy:
  Michael’s leap to LA included appearances at Meltdown with Kumail Nanjiani/Jonah Ray, which served as his career launch pad ([10:58]).

4. Streaming, SNL, and Conan O’Brien

• Both reminisce about late-night and streaming shifts:
  • Michael says, “The only thing I wanted to do in comedy, and I got to do it. And the best guy ever” about Conan ([08:32]).
  • Hilarious family moment: his old roommate’s mom (Carol) stole snacks from the Conan set ([09:03]).

5. Stand-Up Beginnings & Paintball Obsession

• Home club was featured on Bar Rescue (truly, twice—“for the failures” [10:07]); “Howard is unhinged, and it was very real.”
• Paintball as an Adult Hobby:
  Michael spends questionable money on paintball—“I spent my money like I had a guaranteed salary” ([21:08]); describes fields near prisons and their “primal fear” rush.

6. Family, Drugs, and Medical Snafus

• Ketamine, Gout, and Collapsed Lung:
  Grace declares, “Every summer, me, my mom, and my sister say, ‘oh, I’m gonna get gout again’” ([12:35]).
  Michael details a “spontaneous pneumothorax” (collapsed lung from yawning!)—“not even from weed,” though he let people believe it was.
• Pothead Insights:
  Michael’s take: “Pot turns on you, gives you panic attacks for four years, and if you keep going, you stop getting panic attacks.”

  Grace: “Don’t quit. Pussy.” ([16:33])

7. Academic Mediocrity and ADHD

• Both commiserate about terrible GPAs, Adderall, and parents who “didn’t believe in” ADHD.

  Michael: “Every task is a mountain to climb” ([17:32])

8. Impressions, Social Media, and Familial Bonds

• Both attempt Trump and Tucker Carlson impressions.
  • Michael shares he has a voicemail from his late grandmother, with Tucker Carlson ranting in the background.

  “Tucker’s in the back, like…” ([18:52])

• Fandom:
  Michael avidly tracks social media mentions and admits to running a Reddit burner to defend himself ([31:02]).

  “I do have a burner, and I respond to people that are wrong.”

9. Fan Engagement Segment: Videos, Questions, & Memes

• Fans submit TikToks, inside-joke videos, and questions (from Maggie, Sab, Evie, Erin, Asia, Kai/Jada, etc.).
  • Michael often recognizes fan handles, shows genuine appreciation, and playfully rates their bits.
  • Subjects include his favorite movies, future Australian tours, mysterious “Heated Rivalry” (a gay hockey show), and being asked to help fans get into the Jimmy Fallon audience for celebrity interviews.
  • Michael and Grace’s top four films:
    • Michael: Shrek, Shrek 2, Full Metal Jacket, Superbad (also Titanic, Lord of the Rings) ([34:50-36:13])
    • Grace: Titanic, Lord of the Rings, Anchorman 2

10. Mad Libs and Disgraceful Receipts

• Grace makes Michael read a Mad Lib for comedic effect, ASMR-style; joke references to Nikki Glaser and award show tips—“only 420 guys watching, all on oxys” ([56:03]).
• Receipts segment: Grace presents old photos and tweets for Michael to explain or react to, e.g.:
  • His “coke guy/Honda Civic” tweet ([61:44])
  • Childhood lacrosse photos, haunted house dummies, Joe Rogan’s “alpha brain” ([64:12])
  • Threw out the first pitch for the Arizona Diamondbacks ([66:54])

11. Closing Shout-Outs & Plugs

• Michael shouts out Phoenix, Five Iron Golf simulator, Colin Jost, his college roommate James (who brought strangers to an SNL party), and local sports teams.
  • Mentions his tour, dropping gamer tags, and a surreal story:

    “Drake follows me on Instagram a month before Kendrick made him up…He liked a deep crowd work clip. It wasn’t even SNL related.” ([71:30-71:50])

• Grace and Michael end on high energy, hyping up 2026 for both.

Notable Quotes and Memorable Moments

• On therapy and Rorschach tests:

  “Who’s getting prescribed serious medications from an ink blob?”
  – Grace ([02:37])

• On failed auditions:

  “My mom drove me, and it was so horrifying and embarrassing. I just got in the car, we drove back to Arizona.”
  – Michael ([05:41])

• On standup beginnings:

  “You think a headliner’s gonna come save you from this small town? Never happens.”
  – Michael ([10:48])

• On social media and fan edits:

  “I love the fan edits. I send them to my friends.”
  – Michael ([04:19])

• On Adderall and ADHD:

  “My parents didn’t believe in it, so once I got to college, I was like pretty sure I got this thing going on.”
  – Grace ([17:23])

• On running a Reddit burner:

  “If it’s strictly SNL, strictly you talking about yourself, just put a little so obviously reminder in my phone to delete that.”
  – Grace/Michael ([31:04])

• On receiving odd fan DMs:

  “My girlfriend’s mom once sent me a video of cartoon cats singing on YouTube and was just like, maybe for the show.”
  – Michael ([27:06])

• On jobs and lying to get them:

  “I lied to Colin Jost that I golf so he’d take me on the road…humiliated myself.”
  – Michael ([41:49])

Timestamps for Key Segments

• [01:26] – Michael’s billionaire island gig
• [02:55] – Ketamine therapy stories
• [05:27] – First awkward LA audition
• [06:47] – “How to haunt appropriately” thesis
• [08:32] – Conan O’Brien segment memories
• [10:07] – Club on Bar Rescue
• [12:35] – Gout and family genetics, ketamine therapy
• [14:20] – Collapsed lung from yawning
• [16:33] – “Don’t quit, pussy” on weed panic attacks
• [18:52] – Dead grandmother voicemail feat. Tucker Carlson
• [21:08] – Paintball addiction details
• [24:48] – “Is the ice broken?” segment
• [31:02] – Reddit burner confession
• [34:50] – Top four movies (fan question segment)
• [56:03] – Mad Libs with Michael
• [61:44] – Disgraceful Receipts (old tweets and photos)
• [66:54] – First pitch at Chase Field (Arizona Diamondbacks)
• [70:33] – Shoutouts and tour plugs

Tone & Overall Vibe

• Playful, self-aware, and unapologetically off-the-cuff
• Both hosts are quick to roast and riff, but there’s genuine warmth—especially toward fans
• The humor is dry, irreverent, and often veers into the absurd or hyper-specific (as when poking fun at medical events, online culture, or convoluted family trees)

Final Thoughts

This episode is a fast-moving, joke-dense celebration of awkward beginnings, internet rabbit holes, and the realities of both rising and existing in modern comedy. Michael Longfellow’s understated, self-effacing style brings consistent funny, while Grace O’Malley ensures no bit goes unriffed. Fan participation is embraced and lovingly mocked, old tweets are not forgotten, and listeners gain both a sense of community and a highlight reel of what happens when comedians are simply left to be their weirdest selves on-mic.

Find Michael Longfellow on tour at MichaelLongfellow.com, check his socials, and maybe catch him on Xbox—but “otherwise, don’t find me; I stay in the house.” ([72:05])