Disgraceful with Grace O'Malley

Episode: The Haunting of Sally O’Malley ft. Debbie Downer
Date: October 30, 2025
Host: Grace O’Malley (a.k.a. Sally O’Malley)
Guest: Nora (Grace's sister, playing “Debbie Downer”)

Overview

This hilarious Halloween-themed episode of Disgraceful celebrates cringe, nostalgia, and the O’Malley family’s unique take on spooky season. Grace’s sister Nora (“Debbie Downer”) joins in for bits, games, and a roast of Grace’s cultural and horror movie blind spots. Together, they play Halloween guessing games, recount wild family memories—especially haunted house parties gone awry—and take listeners through a comedic walk down memory lane with old Halloween costumes. The episode features signature sibling banter, Halloween antics, and a hefty dose of self-deprecating humor.

Key Discussion Points & Insights

1. Grace’s Sobriety Challenge

• Grace reveals she gave up drinking from September 1st to her birthday, October 27th, intending to keep it private but discusses her determination versus previous failed attempts.
  • “At the end of August, I kind of looked at my friends and I was like, yeah, it’s been a fun summer, boys. I think it’s time to reel it in a little bit.” (00:30)
  • “I’m 45 days in.” (00:58)
• Navigating Sober Social Life: Grace describes resisting peer pressure and the struggle (and placebo effect) of substituting beers with Liquid Death and mocktails.
  • “I have glorious, beautiful, glistening, sweaty, crisp beers waiting for me in the green rooms. And so that's tricky.” (11:18)
• Nora’s classic deadpan:
  • Nora: “Usually you don’t last this long.” (01:18, 09:55)

2. Post-Show Shenanigans and Family Highlights

• Recap of shows in Providence, RI:
  • Dubs it a crowd with “arms crossed, enjoying comedy, which is the worst way to do it.” (07:14)
• Her Dad’s Comedy Debut:
  • Grace’s father performed standup using his phone in large font, inspired by Grace’s inability to get him into a studio to record his unreleased country songs.

3. Halloween Themed Banter: Costumes and Movie Knowledge

• Grace as “Sally O’Malley” for Halloween:
  • “My name is Sally O' Malley and I'm 50 years old. I'm not afraid to tell anyone…” (02:10)
  • Admits the Annie wig makes her look “like an orphan child”
• Recurring ‘Debbie Downer’ Theme:
  • Nora sprinkles bleak or absurdly factual statements throughout, parodying the SNL character.
  • Nora (deadpan): “Over 1 million children under the age of five die before they’re five every year.” (03:19)
  • “If you don’t get your wisdom teeth out, you’re gonna get sepsis.” (06:21)

4. Games & Audience Participation

• Haunt the Plot Game (18:03 – 27:32)

  • Nora reads off extremely vague plot lines for scary or Halloween movies for Grace to guess.
  • Memorable round:
    • Nora: “Cat runs away, but is a person.”
    • Grace: “Cat’s the musical with Taylor Swift.” (18:13–18:15)
    • Answer: Hocus Pocus
    • Rapid-fire banter with constant misguesses, twists, and in-jokes.
  • Some answers: Halloween Town, The Witches, Friday the 13th, The Shining, Beetlejuice, Coraline, It, Scream, The Addams Family, Twitches.

• Heads Up – Costume Edition (34:12–38:49)

  • Describe a celebrity or character based only on how you’d dress as them for Halloween. Hilariously imprecise clues and quick jokes.
  • Highlights:
    • Batman’s “spikes”; green “ogre”—“Shrek”; Tony Soprano; Pennywise; Joker; Eleven (from Stranger Things); Glinda; Jessica Rabbit; Severance; Harry Potter; Chaperone.

• The Fuck on My Hand (39:03–43:02)

  • Halloween sensory challenge: Grace guesses mystery items (spaghetti, potatoes, oobleck, dildo-shaped beans-in-condom).
  • Disgusted but game, Grace delivers new levels of revulsion, links food textures to “ancestral famine.”
  • “In your brain you said, ooh, what a fun segment. This will be. Nothing to do with Halloween, but let’s make spaghetti with potatoes. Make her feel like she’s in Maggot USA.” (41:48)

5. Ghosts of Halloweens Past: Costume Walkthrough (44:37–51:53)

• Grace and Nora roast Grace’s Halloween costumes through the years, from “sailor” in a boutique dress, to a caveman with a cut-up leggings, to “sexy witch” in a family hand-me-down hat, to the infamous “Tekashi 6ix9ine” getup (“That’s a toughie”). See full banter at 46:08–48:42.
• “Life is but a dream” – Recalls sneaking into a UMass party via the window in a feather boa, then being busted by feathers left behind.
• Best recurring costume? Lindsay Lohan – “People tend to like the pop star of which they think they look like. I, in my delusional brain, think I look like Lindsay Lohan.” (51:24)

6. Family Halloween Parties & Trauma

• Details her dad’s DIY haunted house parties growing up, replete with “the unfinished side of the basement as the ‘holding room’ where kids screamed to leave” and her dad scared little ones on the driveway dressed as a clown.
  • “My dad would literally set up in the driveway. He would act like. Like a decoration. And then when kids went to go in for the candy, he’d go scaring them shitless.” (30:06)
  • Nora: “He still does it to this day. He dressed up like a clown like two years ago…” (30:34)
• Grace’s post-party injury:
  • “I fell face first on my head onto the concrete... I think I pretty much have permanent brain damage. But nobody ever looked because nobody was really concerned about concussions back then…” (30:57–31:44)
• Reminiscing about “Halloweekend” at colleges, including anti-climactic parties, underwhelming UMass atmosphere, and “dressing as Tekashi 6ix9ine” for comfort above all else.

Notable Quotes & Memorable Moments

• “I wish I had the confidence of a man. I’ll tell you what. Because he. And I know he’s watching. You crushed it, Dad. You did. But did you mega triple crush it like you think you did?” — Grace (08:10)
• “Cat runs away, but is a person.” — Nora, poorly describing Hocus Pocus (18:13)
• “Alcoholic writer is seeing shit.” — Nora, describing The Shining (21:19)
• “Want to watch YouTube videos, car crashes? What are we doing?” — Grace, on her sober high-energy (11:35)
• “I don’t think it’s funny because I hear you laughing, and I don’t like being laughed at… unless I’m doing the laughing, and I feel like I don’t really have a say in this.” — Grace, during the “Fuck on My Hand” segment (41:16)
• “If you liked it, you liked it. If you didn’t, go fuck yourself. And I’m actually going to be on a cruise during Halloween so go fuck yourself.” — Grace, signing off (51:35)

Important Segment Timestamps

• Grace’s Sobriety Announcement: 00:30–01:54, 09:54–14:15
• Providence Show and Dad’s Set: 07:14–08:10
• Halloween Costume and Debbie Downer Banter: 02:10–03:41, 06:21
• Haunt the Plot Game: 18:03–27:32
• Heads Up Costume Game: 34:12–38:49
• The Fuck on My Hand Game: 39:03–43:02
• Costume Walkthrough and Ghosts of Halloweens Past: 44:37–51:53
• Family Haunted House Memories: 27:57–32:08

Tone & Language

Grace and Nora’s tone is loose, improvisational, and unapologetically candid. The humor is irreverent, self-deprecating, and frequently veers into the absurd, especially regarding family lore and Halloween traditions. Nora’s dry delivery as “Debbie Downer” contrasts perfectly with Grace’s energetic, self-roasting style.

Summary Takeaway

This episode is a chaotic, delightful ride through O’Malley family Halloween traditions—equal parts gross-out games, quippy sibling rivalry, and affectionate takedowns of one another’s (and America’s) Halloween obsessions. If you like off-the-cuff family comedy and biting riffs on memories, costumes, and pop culture rituals, this Halloween episode of Disgraceful is for you.