Hey Riddle Riddle #376: All Pervert's Eve w/ Ross Bryant

Released: October 1, 2025 | Guest: Ross Bryant

Episode Overview

On this festive and slightly unhinged Halloween episode, the Hey Riddle Riddle crew—Adal Rifai, Erin Keif, and John Patrick Coan—welcome the multitalented Ross Bryant (improviser, podcaster, and comedy "royalty" from Chicago) for a chaotic gauntlet of riddles, tangents, and plenty of pervert-themed improv. The episode’s main event is a marathon of 26 alphabetical warmup riddles, each answer following a letter of the alphabet, submitted by listener Shannon. The hosts riff on Chicago nostalgia, the quirks (and cruelty) of riddles, pervert pumpkins, unionizing barn animals, and their own coming-of-age summer jobs, all in their signature improvisational style.

The theme: Halloween, improvisational mayhem, Chicago love, and a riddle marathon frequently derailed by improv scenes and perverse humor.

Key Discussion Points & Memorable Moments

1. Welcome, Ross Bryant! (00:36–05:03)

• Chicago Comedy Royalty:
  The team celebrates Ross Bryant’s Chicago improv accolades, including Improvised Shakespeare and Second City. Ross shares nostalgia for the frigid Chicago winters and the camaraderie it fosters.
  Quote:
  “What I really do miss about it is the camaraderie that it creates, that everybody goes through this annual hazing ritual…” – Ross Bryant (02:57)

• Deep Dive into Chicago Food:
  Extended riffing on Italian beef sandwiches (“wet beef”), giardiniera-as-pepper-spray, and poking fun at deep dish pizza.
  Quote:
  “Hard to defend Chicago food. Hard to sort of die in the hill of deep dish pizza. Sorry, sorry.” – Adal Rifai (04:21)

2. Riddles vs. Trivia—A Battle of Wits (05:03–10:16)

• The group, especially Ross, laments the "villainy" of riddles, which are, in their opinion, meant to infuriate rather than enlighten. They compare riddles’ misleading nature to the logic of Bazooka Joe comics.
• Warmup for trivia nights, performance studies, and the origins of their interests. Quote:
  “Some riddles I’ve encountered are written with pristine mathematical elegance, but it seems the majority of them are written with the logic of a Bazooka Joe comic.” – Ross Bryant (06:05)

3. 26 Alphabetical Warmup Riddles: Riddle Marathon (11:06–70:15)

Format & Structure

• Listener Shannon supplied 26 riddles, answers running A–Z.
• Erin reads riddles; answers must start with the corresponding alphabet letter.
• Hilarious tangents, misreads, and improv scenes ensue.

Highlights & Sidebars

• Alligator Riddle and ‘Flammable Alligators’ Scene (12:07–15:53):
  An improv bit featuring a flammable alligator and a (bourbon-drinking) teacher, Mr. Jeffries, who’s clearly unqualified, riffing on animal wheels and mad scientists.

• Unionizing Animals Scene (22:15–25:38):
  Adal and Ross riff on donkeys forming a barnyard union, taking a swipe at “right to work” legislation and accidental references to Norma Rae and Silkwood.

• DJ Ross Bryant, Teenage Jobs, and Radio Days (29:18–32:44):
  Ross shares tales from working as a radio DJ as a teen, playing short songs to hit the hour and being discouraged from “japes, jests, goofs and gags.”
  Quote:
  “You were distinctly discouraged from doing japes, jests, goofs and gags? No, it was very much a like, hey, what’s up? It’s the top of the hour. And coming up next…” – Ross Bryant (32:01)

• Improv: Talking Clock Needs a Scratch, Pervert Negotiation (18:33–20:27):
  Scene with a perverted clock needing to be scratched, negotiations abound, and inanimate objects request other kinds of “help.”

• Other Scenes:

  • Porcupine parent unwilling to sew (54:15–56:25)
  • Talking Jack-o’-lantern helps a stoned friend get sober (45:53–50:44)
  • Erin’s morbid “Queen for a Day” reign goes off the rails (57:48–61:45)
  • Ross as the Wind, harassing Chicagoans (66:57–69:11)

Notable Riddle Answers

• A: Alligator (12:47)
• B: Blackboard (12:58)
• C: Clock (13:28)
• D: Donkey (22:13)
• E: Egg (44:12)
• F: Fence (44:59)
• G: Glove (45:10)
• H: Hole (45:24)
• I: Ice Cream (45:30)
• J: Jack-o’-Lantern (45:53)
• K: Kitten (51:33)
• L: Lamb (51:35)
• M: Mirror (53:46)
• N: Needle (53:55)
• O: Octopus (53:59)
• P: Porcupine (54:15)
• Q: Queen (57:39)
• R: Road (63:06)
• S: Smoke (63:43)
• T: Trumpets (65:14)
• U: Umbrella (65:24)
• V: Valentine (66:47)
• W: Wind (66:55)
• X: X-ray (69:50)
• Y: Yarn (70:05)
• Z: Z (for "Zzz"—snoring) (70:15)

Quote:
“These were very poetical riddles. Hats off to Shannon.” – Ross Bryant (70:28)

4. Pervert Energy & Scene Work (Multiple timestamps)

• The “pervert” motif is ever-present, peaking with "All Pervert’s Eve" gags, the existential pervert Jack-o’-lantern, the “NC-17 Brave Little Toaster,” and more. They joke about October being for perverts and November for kid-friendly content. Quote:
  “We celebrate Pervert day, which is October 8th every year.” – Erin Keif (56:35)

5. Chicago & Midwest Sidebars

• Ross waxes poetic about the city, the food, and the weather.
• Chicago-specific improv: “Go Cubs” vs. “Go Sox” and exaggerated local lingo.

Notable Quotes & Moments

• “Riddles… their match is their medium… It’s trolls and crafty warlocks.” – Ross Bryant (06:36)
• “You can see [the alligator’s] snout up here, the tail back here, and of course, the wheels down below.” – Ross Bryant as Mr. Jeffries (16:12)
• “What I’m offering you is some petty authority over the other animals in the barnyard.” – Ross Bryant (24:46)
• After a pervert pumpkin saga: “How do you fuck a pumpkin? …It's pretty straightforward.” – Adal Rifai & others (51:10–51:16)
• “Perverts all the way down.” – John Patrick Coan (74:46)

Important Timestamps

• Ross emerges from the storage unit: 01:51–02:10
• Chicago comedy/winters/food riff: 02:12–05:03
• Ross on riddles vs. trivia: 05:03–06:49
• Start of Alphabet Warmup Riddles: 11:06
• Alligator improv scene: 13:22–15:53
• Union donkey scene & “right to work” tangent: 22:15–26:17
• Porcupine sewing scene: 54:15–56:20
• Jack-o’-lantern (stoned improv): 45:53–50:49
• Pervert motif acknowledged: 56:34–57:54
• Queen for a Day improv chaos: 57:48–61:45
• Ross as the Chicago wind: 66:57–69:11
• Completion of the 26 riddles: 70:15
• Ross plugs new podcast: 70:40–74:46

Closing & Plugs

• Ross Bryant promotes his new actual-play podcast: Push the Roll with Ross Bryant
  • Improv Call of Cthulhu, with guests like Matthew Lillard, Becca Scott, Brennan Lee Mulligan, Matt Young, and more—including the Hey Riddle Riddle crew.
• Improvised Shakespeare continues their run in LA and upcoming tour dates in Atlanta, Nashville, and Chattanooga (LA’s Largo Theatre, October 2025).
• Hey Riddle Riddle Live! Upcoming shows in Atlanta, Nashville, Denver.
• John Patrick Coan—watch Ross’s Tom Waits impression on Game Changer (YouTube/TikTok).
• Gumshoes & Dragons podcast, new episodes out.
• Patreon: More listener hot takes and behind-the-scenes content.

Quote:
“It’s a very smart, highbrow show. But we definitely still do play Pervert Pumpkins.” – Ross Bryant about Improvised Shakespeare (74:38)

“You didn’t choose. This is all of our brains working together in the strange alchemy of improvisation. And there’s one rogue element, one X factor that has brought pervisation to you.”
– Ross Bryant (56:54)

Summary

This episode covers an ambitious A–Z riddle challenge but constantly digresses into improvised scenes about perverts, talking pumpkins, barnyard labor politics, and much more, all filtered through the lens of Chicago comedy nostalgia and Halloween chaos. The gang’s signature banter and Ross Bryant’s sharp wit make it both a celebration of silly improvisation and a highlight reel of comedic one-liners and tangential brilliance. Whether you're a riddle fan or just there for the bits, it’s a perfect (unhinged) Halloween listen.