Riddles as bait, derailments as sport.
Hey Riddle Riddle is a riddle-solving comedy show that treats answers as optional and derailment as craft. Puzzles, sponsor reads, game-show bits, museum lock-ins, and period-romance premises all become excuses for fast group improv.
PRESS PLAY
Hey Riddle Riddle is built like a riddle show and behaves like a panel improv machine trying to chew through its own format. The premise is simple. Someone brings puzzles, wordplay, games, or a fake structure, and the group tries to solve it until a stranger, phrase, sound, or wrong answer becomes more tempting than the answer itself. Then the show bolts. Recent episodes turn count-ins into semantic arguments, customer complaints into silent-letter spirals, and wine tastings into scenes about plastic cups, bad deals, and bleeding backs. A period-romance parody becomes a courtship contest full of riddles, flirtation, status games, and immediate rule-breaking. Patreon previews stretch the same muscles through museum lock-ins, game-show sequels, tech nonsense, and penguin baseball drafts. The show is quick on its feet. It likes a clean setup, but it loves a broken one more. Sponsor reads and promotional sections can be unusually visible in the sample, yet even those often become part of the comic machinery rather than a pause outside it. The panel rhythm is central: objection, correction, escalation, brief shame, restart. Nobody has to protect the premise for long, because the fun is in watching the premise get dented. Guests fit into that momentum by feeding the game rather than calming it down. The humor is loose, adult, and often absurdly specific. It is not a tidy puzzle club. It is closer to a room of performers using riddles as bait, then rewarding the funniest misread, the dumbest commitment, and the scene that probably should have ended thirty seconds ago. That looseness is the point. For listeners who like comedy that openly admits when it has gone off the rails, Hey Riddle Riddle makes the derailment feel like the main event.
Made for: Best for listeners who like fast panel improv, wordplay, fake formats, and comedy that treats wrong answers as opportunities. It suits people who want riddles with mess, not a polished puzzle contest.
What sets it apart: The show stands apart by making the failed solve, the tangent, and the collapsing bit feel more important than the riddle itself. Its sponsor-read mutations, genre parodies, and scene work give it a restless improvised texture.
Riddles! Puzzles! WhoDunnits! Adal Rifai, Erin Keif and John Patrick Coan, three of Chicago's most overrated improvisers, are on the case to solve every riddle, puzzle, brain-teaser, and head-scratcher known to humanity. Some riddles are almost impossible, some are absolutely improbable, and some simply have not aged well. And if you don't like riddles, don't worry! This podcast is barely about them! Like what you hear? Join the Clue Crew for weekly bonus episodes at Patreon.com/heyriddleriddle
Based on 6 episodes we listened to · September 2026
Riddles provide the spark, while three quick improvisers turn wrong answers and stray details into increasingly elaborate comic worlds.
Hey Riddle Riddle turns puzzles into launchpads for Adal Rifai, Erin Keif, and John Patrick Coan. A clue may receive a serious attempt, a gleefully wrong answer, or an improvised scene that overtakes the original problem.
Cat surgery enters a toy pitch, and you get to watch the meeting lose the plot.
Press play if you want
Short reviews from the PlayNext desk, based on the episodes we processed.
A stalled answer opens into fake hands, leaking condiments, and a Rocket Money turn.
This single-episode review is strongest when it tracks Casey's almost-answer into the space around it. His decision to hold back a thought leaves the conversation hanging on breath, inflection, and hesitation, until a small pause begins to feel like league trouble.
A storm, a stubborn umbrella, and a phone call that keeps small mistakes from staying small.
This episode turns a storm into a shared problem and then watches the plan slide sideways. An umbrella gets too much confidence, someone refuses to stay out of the rain, and a phone call drifts into names, pasta shapes, and silent letters.
A filthy title chain turns into wine-tasting chaos and a shaky three-star truce.
Hey Riddle Riddle turns a listener-voted review slot into a parade of filthy parody names and escalating bits, with the panel tossing out one fake title after another as the conversation keeps slipping into new territory.
A courtship riddle tournament where polished answers keep turning gross.
The episode recasts a debutante season as a riddle contest, letting the Queen steer Miss Arabella Riddleslark's courtship through conundrums rather than waltzes, duels, dowries, or polite chatter about the weather.
A cheap Taco Bell slogan leads into toy surgery, brand confusion, and a riddle payoff.
A fast-food rebrand turns into a slogan dare when Taco Bell's return to 1986 prices runs into the problem of still using "run for the border." The pitch settles on "Cheap dong," then veers into a toy-company boardroom where CEOs hear out "Cat a talk," a surgery-based kid-cat…
A stormy outing and a cookie complaint turn strained politeness into escalating nonsense.
Aaron's oversized umbrella turns a monthly outing into an exercise in careful manners, where watching the sky during a storm somehow passes as a normal plan.
A mythical-creature baseball draft turns league rules, abandoned comments, and an alleged portal into escalating panel chaos.
A routine baseball draft is quickly pushed into stranger territory by a portal, mythical creatures, and a league rule meant to keep owners from fighting.
Tiny debates, treated with heroic seriousness.
Casey almost says something.
Nobody keeps charge for long here.
The hosts discuss winning a storage unit bid and speculate about potential valuable finds inside, while also promoting the Hacks podcast and TV series.
The Hacks podcast returns for the final season of the Emmy-winning comedy series, featuring creators and showrunners sharing behind-the-scenes stories from the set and writers' room.
The hosts discuss a letter from the Riddle Podcast Union requiring them to have understudies for their podcast.
The episode discusses the final season of Hacks with its creators and transitions into Hey Riddle Riddle's tradition of making yearly predictions for 2026.
The Hacks podcast returns for the final season of the Emmy-winning comedy series, featuring creators discussing behind-the-scenes stories while camping and making cowboy coffee.
Hey Riddle Riddle’s Patreon preview “Penguin Baseball Draft Season Three w/ Janet Varney & Casey Toney” turns into a draft of mythical-creature baseball teams.
The episode opens on a chaotic outdoor hang and keeps making the weather somebody else's fault.
This episode previews the Hacks podcast, featuring creators discussing the final season of the Emmy-winning comedy series, with humorous banter about technical issues and a guest appearance from Penguin Baseball founders.
This episode promotes the Hacks Podcast, which features creators and showrunners discussing the Emmy-winning comedy series Hacks as it concludes its fifth and final season on HBO Max.
This episode continues a game show-style segment where hosts discuss prizes and sequels related to the comedy series Hacks.
Hey Riddle Riddle frames the bit as an $8-tier review crew episode and then promptly stops pretending it plans to behave.
The Queen has grown bored with The Season, so she makes two gentlemen compete for Miss Arabella Riddleslark's hand with riddles, conundrums, and mischief.
["Hey Riddle Riddle #399, \"Tedd-99,\" opens with a fake Taco Bell meeting about 1986 prices, 39-cent burritos, and a slogan search that rejects \"run for the border.\"", "Erin Keefe, John Patrick Cohen, and Adel then introduce the show, joke about coffee versus energy drinks, and riff on Arnie Parrott, Donovan's \"I Love My Shirt,\" and a made-up apology song.", "The episode moves into a National Cat Day story about Wake County's Alice Avery, her cat Cheese, and a toddler who named future pets Jelly Bean, Popsicle, and Cockadoodle Doo.", "Ted's \"Animal Pun Raid\" riddles carry the rest of the episode, with clues that turn into answers like haircut, spider, impossible, deficient, irrelevant, and koala-fication."]