Hey Riddle Riddle #372: "My Hearts Don't Lie" w/ Joey Bland — Summary

Date: September 3, 2025
Podcast: Hey Riddle Riddle (Headgum)
Hosts: Adal Rifai, Erin Keif, John Patrick Coan
Guest: Joey Bland (Improvised Shakespeare Company, Like Minds podcast)

Episode Overview

This high-energy episode spotlights Chicago improv fixture Joey Bland, diving into his experiences in the world of trivia (including a Jeopardy! run), his complicated relationship with riddles, improv nerdiness, and classic Hey Riddle Riddle goofiness with riddles, lateral thinking puzzles, and wild improv scenes. The episode strikes its usual balance: plenty of "barely about riddles," rich in digressions, stories, and spirited bits.

Key Discussion Points & Insights

1. Joey Bland: Improv and Jeopardy Royalty

• Tattoo Bit: The hosts joke about getting interconnected podcast-title tattoos, with Joey as "the pause" between their words.
• Joey’s Background: Introduced as a notable Jeopardy! contestant and pillar of the improvisational scene.
• Stage Name Gags: Joey recounts audition confusion over his "bland" last name, joking he’s “Joey Razmatazz” in real life (02:32).

Jeopardy! Deep Dive

• Joey's Jeopardy! credentials:
  • "I was on it in 2005. Uh, I won twice and lost once. And you go, everyone loses once." (03:18)
  • Final Jeopardy stories:
    • "Remember the ladies?" — the Abigail Adams clue (04:12)
    • "What is the oldest capital city in the Americas?" — Santo Domingo (04:47)
  • Regret over Final Jeopardy wagering: "Never bet everything. You can't win with zero. You can win with a dollar." (06:56)
  • Hosts riff on Jeopardy betting strategies, website guides, and the sadness of being benched in Final Jeopardy (07:29).

Trivia vs. Improv Skills

• Joey says a broad array of knowledge helps in improv but "not knowing a lot of stuff, but being interested in a lot of stuff" is most helpful (10:13).
• On Alex Trebek: "On the day, I didn't feel that at all... He was really good at it." (11:13) — plus some classic Trebek ribbing.

2. Riddles, Puzzles, and Escape Rooms

• Joey’s relationship with puzzles: "I always know what I'm supposed to do... but I can't do it until it just happens. So I feel like it's very frustrating. Yeah, I hate them in a lot of ways." (12:11)
• Prefers constructing over solving: "I like being the person constructing the puzzle box... I guess I'm that side of, like, the sadism of it." (12:53)
• "Puzzlier than straightforward trivia": Joey likens his Like Minds podcast questions to what a "bridge troll" would ask (13:24).

3. User-Submitted Riddles & Improv Scenes

Riddle 1: "Nose and tail, but cannot breathe"

• Multi-layered attempts:
  • "Is this like a penny?" — "Acceptable, but it’s not the one we’re looking for." (14:44)
  • Plane, scooter, transportation device ("Skateboard!"), culminating with skateboard as the answer (18:38).

Notable Scene: Dad at the Skate Park

• Hilarious improv where Adal plays a dad disastrously trying to connect with skate kids (19:08–23:17).
• "Dude, your pants are ripped bad." "Oh, my toxic!" — Erin as kid, at 19:39.
• Wild escalation: Old Bart Simpson skateboard, exploded tomato/testicle confusion, Carol Channing as a kid’s name.

Discussion: 90s Pop Culture

• Dr. Pepper Pizza Hut skateboard, Bam Margera confusion, Aggro Crag from Nickelodeon Guts, Legends of the Hidden Temple nostalgia (23:22–25:19).

Riddle 2: "Corrupt king—both papers say guilty"

• Joey narrows in on solution: "I think you go… you grab both pieces and you open them…" — but the answer is:
• Eat one piece of paper, forcing the king to reveal the remaining “guilty” slip, thus appearing you picked “innocent” (31:53).
• Clues from JPC: "Your hands are free." (29:03)
• Improv Scene: Vaudeville duo stalls the king before execution with puns and jokes (32:37–36:29).
  • "If these are the last words I can speak in my entire life, take me, please, away from my wife." — Joey as vaudeville husband.

Riddle Games: Real or Fake? (Elvis Brown's Set)

Each set: one real riddle, one nonsense red herring.

Set 1:

• "What is always on its way but never arrives?" (Fake; but hosts answer "future" or "tomorrow")
• "What makes tears without sorrow and takes its journey to heaven?" — Answer: Smoke (57:30)
  • "Balloon" is suggested, leads to a scene with Erin’s stepdad as a balloon (52:10–56:41).

Set 2:

• "I rise and fall, no matter what. Only at final rest do I not budge. What am I?" — Answer: Feet (65:22)
  • EKG machine, eyelids, elevator, tide all guessed.
  • Notable: Joey’s banter about "coma machine," “Smith Scholar” joke.
• "I have no legs to dance and no lungs to breathe, yet I do all three." (Fake; hosts roast the bad riddle.)

Set 3:

• "Although I'm not an insect, ... called me the insane priest. First half of my name means 'scrape', last three letters a metal."

  • Answer: Rasputin (70:55)

  • Hosts find the riddle convoluted and hilarious.

  • "Throw me off the highest building and I'll not break; put me in the ocean and I will leave a grieving wife." — (Fake)

Notable Quotes:

• "You would rather be Jigsaw than the person who has to cut their own arm off?" — JPC, to Joey (13:05)
• "I like this guy's writing!" — Joey riffing on JPC's "scream at the waiter" anxiety blog (07:56)
• [On historical riddles]: "That's barely even a riddle. That's just like a historical fact." — Joey (71:21)
• "Ekg. Machine—yeah, they call them coma machines." — Joey (59:06)

Notable Moments, Running Gags & Quotes

• 03:45 – "Remember the ladies?" Adal references the famed Abigail Adams quote.
• 10:02 – "With improv, period, the more you know, the better, right?" — Joey
• 11:13 – Candid take on Alex Trebek’s game-show hosting style.
• 19:06–23:17 – Multiminute wrestling, skateboard, and skatepark improv mayhem.
• 32:37–36:29 – Extended vaudeville duo execution scene, improvising and stalling with puns.
• 52:10–56:41 – Scene: Erin’s new stepdad is a guidance counselor balloon with a face.
• 67:02–70:14 – Scene: stapled-together phone bill and birthday card, marriage analogy, leading to a melodramatic card sacrifice.
• 71:45–74:51 – Scene: Joey as Rasputin smugly returns to a bar after his (alleged) assassination.

Joey Bland Plugs & Callouts

At 75:28:

• Like Minds podcast ("troll bridge-level trivia," Wednesdays).
• Improvised Shakespeare Company – touring and LA shows.

Erin & Adal Plug:

• Listen to their Like Minds appearance.
• Patreon bonus episodes, "Gumshoes and Dragons", and upcoming Hey Riddle Riddle live tour (76:28).

Timestamps for Important Segments

| Time | Segment | |----------|---------------------------------------------------------------------------------------| | 02:32 | Joey Bland on “bland” as a last name/stage name | | 03:06 | Joey on Jeopardy: victories, Final Jeopardy stories | | 06:56 | Betting mistakes/regret on Jeopardy | | 10:02 | Knowledge in improv context | | 12:11 | Joey on his “hate” for riddles | | 13:24 | Like Minds podcast: “troll bridge” riddle writing | | 14:27 | Riddle: “nose and tail, but cannot breathe” | | 19:06–23:17 | Skatepark improv with “dad” | | 29:03 | King’s riddle; “your hands are free” clue | | 31:53 | Solution: eat one paper to save your life | | 32:37–36:29 | Vaudeville duo execution pun scene | | 49:53ff | “Real or fake” riddle game: various user submissions | | 52:10–56:41 | Scene: Erin’s balloon stepdad scenario | | 65:22 | "Feet" as the answer to rise/fall riddle | | 71:12ff | Rasputin scene in bar after being “exterminated” | | 75:28 | Joey plugs Like Minds podcast and Improvised Shakespeare | | 76:28 | Hosts plug Patreon, Gumshoes & Dragons, tour |

Tone & Style Highlights

• Effortlessly silly, boisterous, and meta—the cast constantly riffs on each other and their own format.
• Joey fits right into the playful banter, indulging the show’s sprawling tangents and intricate bits.
• Smart but accessible: plenty of “dad joke” and vaudeville humor woven into genuinely clever riddle-solving approaches.

Conclusion

This episode is classic Hey Riddle Riddle: a joyful jumble of actual riddles, sprawling tangents about game show history, pop culture, and absurd improv scenes. Joey Bland’s improv and trivia prowess shine through, making him an ideal guest for a show about almost everything and only sometimes about riddles.

Selected Quotes:

• "Not knowing a lot, but being interested in a lot..." — Joey Bland (10:13)
• "You would rather be Jigsaw than the person who has to cut their arm off?" — JPC to Joey (13:05)
• "That's barely even a riddle, that's just like a historical fact." — Joey on the Rasputin puzzle (71:21)