Hey Riddle Riddle #379: Jennifer Monster Popcorn
Host: Headgum
Date: October 22, 2025
Overview
This episode of Hey Riddle Riddle brings listeners a signature blend of absurd improv, playful banter, and mind-bending riddles. Erin Keif, Adal Rifai, and John Patrick Coan (JPC) kick off with Adal’s bold new character creation, Jennifer Monster Popcorn, dive into riddle submissions from a devoted superfan, brainstorm Halloween costumes, and descend into multiple comedic tangents and improvised scenes. If you come for the riddles, you’ll stay for the comedic detours, affectionate teasing, and surprising depth lurking beneath the goofiness.
Main Themes
- Silly character work and creation (Jennifer Monster Popcorn)
- Absurd, layered improv scenes born from riddles
- Listener participation and extreme fandom
- Halloween costumes and pet dress-up
- Riddle-solving with wild, winding logic
- Underlying friendship and comedic chemistry
Key Discussion Points & Insights
1. Jennifer Monster Popcorn: The Perfect Character?
[00:37–03:36]
- Adal bursts in energized and sleep-deprived, claiming he’s created “the perfect character.”
- Erin and JPC volley back and forth, lampooning and attempting their own takes, riffing on the strange name and concept.
- Adal (on creation process):
“I had to roll around in the dirt under the moon to come up with the perfect character... Jennifer Monster Popcorn may sound like a bad—” [00:48]
- Adal (on creation process):
- Erin’s Jennifer is bizarrely both a news producer and a news subject, with a wealthy popcorn family.
- Erin: “‘My family is very rich and I go to boarding school in Sweden and—nuts. No, sweet.’” [02:28]
- The segment seamlessly flows into meta riffing on whether any of this “works” and roasts themselves on their improv excesses.
2. Spooky Month: Pet Costumes and Halloween Talk
[04:56–11:14]
- The hosts chat about Halloween plans—Erin will be out of town and might dress her dog Lou as Paddington Bear or Samwise Gamgee. Pet costumes are debated at length.
- Erin: “I might dress Lou up as Paddington Bear... or Samwise Gamgee.” [05:26]
- JPC (on dog costume anxiety): “My dog has too much anxiety for me to, like, do something to her.” [07:13]
- A hilarious story from Erin about surprising her partner “Zorp” with Lou dressed in a chicken costume (and accidentally getting kneed in the groin).
- Adal shares he dresses up his cats (“Teenie” melts hearts in a cowboy hat), sparking debates over pet boundaries and adorable photo opportunities.
3. Listener Riddles from Superfan Andrew
[11:30–41:00] (spanning multiple interludes)
- Erin introduces a special collection of riddles from loyal listener Andrew, who’s listened to the show multiple times and provided regular email updates.
- Erin (reading Andrew’s progress): “I’ve now listened to every episode... five times. And in case you were wondering, I listen at a normal 1x speed and don’t listen while sleeping. I just listen all day because I have issues.” [13:14]
- The hosts improv a mock Macy’s parade in Andrew’s honor, complete with floundering commentary and parade floats (mostly referencing Snoopy and Peanuts, getting sidetracked as usual).
- Riddles posed by Andrew spark one-to-three-person scenes, wordplay, and meandering guesses. Examples:
- Riddle 1: “My steed's made of plastic or wood or steel, but I'm often soft and pleasant to feel... What am I?”
Solution: Tablecloth - Riddle 2: “My first is a sibling, just one of four. If you’re allergic, I may make your nose sore... What am I?”
Solution: Spring - Riddle 3: “I’m hung on a cross and stretched paper thin. But I'm played with by children and have committed no sin..."
Solution: Kite
- Riddle 1: “My steed's made of plastic or wood or steel, but I'm often soft and pleasant to feel... What am I?”
- Logical leaps often get detoured into playful, sometimes irreverent scenes (e.g., the “Jesus and Judas on a plane” bit [33:02–37:48]).
- Andrew’s multi-year superfan devotion is both admired and lightly teased, with the hosts playfully debating what counts as “most listened” and when to throw another parade.
4. Improv Scenes and Absurdism
- Several riddles launch directly into bizarre improv. Highlights include:
- The Four Seasons debating at a restaurant, anthropomorphizing spring, winter, and summer ([28:36–32:14]).
- The classic "Jesus and Judas after the resurrection" bit, set on an airplane, full of accidental blasphemy, meta-commentary, and classic “wrong seat” chaos ([33:02–37:48]).
5. Meta-Humor & Running Gags
- Endless callbacks to overused bits (“Kyle XY,” peanut gallery rules on old commercial quotes).
- JPC: “We talk about Kyle XY way too much on this podcast.” [50:15]
- Playful feuding over who did or didn’t “get” a riddle answer, and confusion between real and ironic responses.
- Erin lays down a commandment: “Do not quote old commercials!”—sparking a burst of rule-breaking and nostalgia.
6. Listener Voicemail: Radiology Tech vs. Dental Hygienist
[57:54–61:18]
- The crew fields a listener question about choosing between two healthcare professions, offering advice based mostly on occupational vibes.
- JPC: “Radiology tech—if you have a conversation with a person, they can usually converse back. Dental hygienist... it's a one-sided conversation, because you got your hands in someone's mouth.” [58:44]
- The question devolves into debates about pay, work depression, and who talks more on the job, ending with a consensus (“radiology tech”) followed by a realization that dental hygienists earn more.
- Erin (finding out): “Oh, no. Dental hygienists generally make more money.” [60:32]
- Self-depreciating warning: don’t actually trust us with real life decisions!
Notable Quotes & Memorable Moments
- Adal (announcing character): “Jennifer Monster Popcorn may sound like a bad—” [00:48]
- JPC (Halloween): “My dog has too much anxiety for me to, like, do something to her.” [07:13]
- Erin (chicken costume story): “Lou was dressed like a chicken and he was in a ton of pain... we laughed for, like, 90 minutes.” [08:09]
- JPC (parade float): “That's Snoopy. Of course, it wouldn't be a five time listener parade without that big fucking Snoopy in the air.” [15:25]
- JPC (meta-commentary): “We talk about Kyle XY way too much on this podcast.” [50:15]
- Erin (parade meta): “Do not quote old commercials. That's the number one rule in this classroom.” [52:15]
- JPC (life advice): “Maybe that's not our area of expertise. We're more of a Pepsi or Coke panel.” [61:04]
- Adal (on job choosing): “Radiology... is still kind of fun and mysterious. It's, like, modern day magic. So... you could say you're a magician.” [59:16]
Guest Participation & Community
- Ultra-fan Andrew’s emails and riddle-sending create a narrative thread through the episode, letting the hosts dramatize, roast, and ultimately appreciate their most extreme devotees.
- A live advice voicemail gives listeners a chance to connect personally, even prompting the hosts to question their own credentials.
Segment Timestamps
- 00:37–03:36: Jennifer Monster Popcorn character creation
- 04:56–11:14: Halloween & pet costume chat
- 13:14–18:07: Listener Andrew's “five-time parade” and first riddles
- 18:19–28:29: Riddle-solving and tablecloth improv family scene
- 28:36–32:14: Seasons as restaurant guests
- 33:02–37:48: Jesus & Judas airplane scene
- 41:48–43:59: [AD BREAK] (skipped in summary)
- 45:05–46:38: Update on Andrew's listen count/fan devotion
- 47:05–55:10: More riddles, Kyle XY callback
- 57:54–61:18: Listener voicemail on career decisions
- 61:18–End: Closing plugs, call-backs, sign-off
Podcast Plugs & Closing
- Gumshoes and Dragons: New actual play podcast from the hosts.
- HeyRiddleRiddle.com/live: November live shows and ticket info.
- Erin’s Instagram: (For links to household items and more)
- Magic Tavern Podcast: JPC guest appearance.
- Gutter: Editor Casey’s actual play podcast.
Tone & Style
Relentlessly playful, self-mocking, quick-witted, and anchored by genuine friendship. The hosts’ chemistry and willingness to improvise wildly leads to delightfully digressive scenes that sometimes barely relate to the riddles at all—par for the course for Hey Riddle Riddle.
Ideal for...
Fans who love Hey Riddle Riddle’s off-topic bits, recurring gags, and meta-humor, as well as newcomers who enjoy improv comedy and group chemistry just as much as actual puzzles.
In summary:
This is a prime episode for those who enjoy a heady mix of silly character work, community involvement, and unpredictable improvisation, with moments of surprising warmth and always, always, plenty of laughs.