

Hey Riddle Riddle
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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
Episodes
Mentioned books

Dec 19, 2025 • 11min
Patreon Preview #354: 2025 Out of Context Clip Brackets
Listen to the rest with a 7 day free trial at our Patreon!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Dec 17, 2025 • 1h 2min
#387: Lincoln's Lost the Sauce
We only make Erin almost lose it three times this episode, so we are really slipping. And also Sandy is back!Starring:Adal RifaiJohn Patrick CoanErin KeifGuest Starring:Sandor WeiszEditing by: Casey ToneyTheme by: Arne ParrottLogo by: Emily Kardamis & Emmaline MorrisWant more? Get Weekly Bonus Eps on Patreon!JPC's Guided Meditations Volume 1, available now at our Patreon digital store!Want merch? Visit our Dashery Store!Want to mail us something? Hey Riddle Riddle 6351 W Montrose Ave #267Chicago, IL, 60634Want to leave us a voicemail? Call (805) RIDDLE-1 or (805-743-3531)Want to advertise on the show? Check out Hey Riddle Riddle via Gumball.fmSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Dec 12, 2025 • 10min
Patreon Preview #353: Deck the Hallmark
Listen to the rest with a 7 day free trial at our Patreon!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Dec 10, 2025 • 1h 5min
#386: Dad ASMR
Even dads deserve ASMRStarring:Adal RifaiJohn Patrick CoanErin KeifEditing by: Casey ToneyTheme by: Arne ParrottLogo by: Emily Kardamis & Emmaline MorrisWant more? Get Weekly Bonus Eps on Patreon!JPC's Guided Meditations Volume 1, available now at our Patreon digital store!Want merch? Visit our Dashery Store!Want to mail us something? Hey Riddle Riddle 6351 W Montrose Ave #267Chicago, IL, 60634Want to leave us a voicemail? Call (805) RIDDLE-1 or (805-743-3531)Want to advertise on the show? Check out Hey Riddle Riddle via Gumball.fmSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Dec 5, 2025 • 11min
Patreon Preview #352: The Nativity Pageant
Delve into the hilarity of a nativity pageant rehearsal full of delightful chaos. Erin navigates comedic interruptions as cast members vie for roles, including the debate over the perfect Mary for a five-year-old. Big Ed hilariously asserts himself as Baby Jesus while also bickering about Subarus. The team brainstorms celebrity cameos, contemplating who should grace the stage alongside Glinda and Elphaba. Amid song ambitions and a break for snacks, the laughter flows as they tackle the challenges of casting newborns and ensuring the show goes on!

Dec 3, 2025 • 60min
#385: I want to say Cookie Wolf?
In this lively discussion, the hosts engage in hilarious banter about black eyes, fainting, and chaotic holiday travel. They dive into a comedic riddle game featuring cereal mascots, with Adal embodying the whimsical 'Cookie Wolf.' The trio shares amusing stories about Halloween candy traditions and neighborhood quirks. They tackle a series of quirky puzzles, including rhyming animals and surreal sketches, wrapping up with a side-splitting portrayal of a Middle-earth parody. It's a delightful mix of riddles and laughs!

Dec 1, 2025 • 54min
*UNLOCKED* Clue Crew #301: Merry Christmas to Mall and to Mall a Good Night!
The hosts kick off with hilarious mall-themed sketches that set a festive tone. A last-minute lingerie shopping scene leads to comedic mannequin mishaps. Chaos ensues at a perfume counter meeting, showcasing the team's comedic skills. They explore absurd Santa encounters, including drunk Santas and mall security. The discussion turns to bizarre kiosk vendors and a frantic Lego store skit. Amidst humorous debates on pizza and relationships, the antics culminate in a wild report about a missing Santa and unexpected discoveries!

Nov 28, 2025 • 11min
Patreon Preview #351: Mission to Mars Draft
The hosts kick off a hilarious banter about space travel and personal fears of flying with unfriendly neighbors. They dive into the discomforts of commercial space voyages, likening them to air travel. The debate heats up around Elon Musk's ambitious Mars plans and the seemingly unending wealth of billionaires. A lively Mars draft ensues, complete with lively arguments on whether humans could survive on the Red Planet. Expect plenty of laughs and witty commentary throughout!

Nov 26, 2025 • 1h 4min
#384: The Return (really!) of Kid Friendly
A delightful treat for families, the hosts launch into kid-friendly stand-up, tackling everything from Halloween candy to winter antics. They solve classic riddles while improvising funny sketches, including a birthday genie with twisty gifts. The discussion flows to seasonal blues, touching on mental health and online therapy experiences. Listener-submitted riddles spark laughter, especially with a cowboy dachshund joke. The banter is lively as they wrap up with playful tips and a call to enjoy childhood adventures!

Nov 21, 2025 • 11min
Patreon Preview #350: The Beak & Bones Society
Listen to the rest with a 7 day free trial at our Patreon!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.


