Headgum

Hey Riddle Riddle

Leisure EN ↓ 681 episodes

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

Author

Headgum

Category

Leisure

Podcast website

art19.com

Latest episode

Jul 10, 2026

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Episodes

Patreon Preview #152: Chatterbox 4 11.02.2022

Listen to the rest 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 .

#186: Quit Grabbing Eagles w/ Matt Young 09.02.2022

This week we have special guest Matt Young ( Hello From the Magic Tavern Podcast , Dear Earth, I'm Really Sorry Podcast ) on to nerd out on Majora's Mask, pretend to be in the Chicago Fire, teach Smokey the Bear a lesson and bring back everyone's favorite blue wizard....WIZZY!!! Hitch a ride on the nearest bird, it's time for Hey Riddle Riddle! Starring: Adal Rifai John Patrick Coan Erin Keif Spec...

Patreon Preview #151: Hey Riddle Station Part 2 04.02.2022

Listen to the rest at our Patreon! See omnystudio.com/listener for privacy information. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

#185: Dr. Very Good Body w/ Johnny O'Mara 02.02.2022

This week we have special guest Johnny O'Mara ( The Billbuds Popcast , The Campaign Podcast , and Dilettante Ball ) on to talk about his puzzle trauma and also do some improv make-em-ups. Plus we've got a school for the gifted, the dreams of the young, the dark side of a childhood favorite, a group of friends that's all a-buzz, some insight into a classic cartoon, and a delicious date! Starring: A...

Patreon Preview #150: Hey Riddle Station Part 1 28.01.2022

Listen to the rest at our Patreon! See omnystudio.com/listener for privacy information. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

#184: Johnny Scramblers & The Heartbreak Pumpkins 26.01.2022

We hope you need a name for your band-because we’ve got plenty! We have some listener submitted riddles this week-And a desire to kill some time before we read them. This episode also has time travel, a snake biting off more than it can chew, and a very dignified conversation between a hound and a fox. Pull! Happy Wednesday!  Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey Tone...

Patreon Preview #149: Welcome to New Jersey💡 21.01.2022

Support the show and listen to the full episode now by joining our Patreon! See omnystudio.com/listener for privacy information. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

#183: Happy Pasta Day! 19.01.2022

We are ready to celebrate, baby! Pasta Pasta Pasta! This week we have some great listener submitted riddles- some that are even written down on a piece of paper. This episode has some disney characters, a plea for money, Fortnight, and a terrifying Night Mare. JPC and his little helpers hope you have a great week! Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey Toney Theme by: ...

Patreon Preview #148: Listener Scenes Volume 1 14.01.2022

Support the show and listen to the full ep now by joining our Patreon! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

#182: Which Pisswitch 12.01.2022

It's our 2nd ep of the New Year so you know we're going to talk about our New Year's Eve! Also, Adal unveils his new word for 2022 and, spoiler alert, it's in the title of the ep. All that and we've got a new bird in town, a chance encounter in the woods, a joyous celebration at a somber occasion, an unruly teen with an unruly ween, and a total POS on a first date. Are you ready for another year o...

Patreon Preview #147: Troubled Fairy Tales Pt. 2! 07.01.2022

Enjoy a sneak preview of today's new Patreon exclusive episode! It's back baby! We're improvising some more Hans Christian Andersen fairy tales based on just the titles! Have we created a new classic tale? Will these stories be populated with more terrible people and troubled animals? Should children listen? (No. Yes. No.) Want more?  Get Weekly Bonus Eps on Patreon! Starring: Adal Rifai John Patr...

#181: Happy Clue Year! 05.01.2022

Happy Clue Year all you Riddiots! We're thrilled to start 2022 and have this episode as PROOF we still 'love' riddles! In this episode we have tips for a job interview, a heated scene between two numbers, an idiotic ring bearer, parts of a clock trying to bury the past and the world's longest Home Run! Toss back some champagne, surpress your real pain and escape for an hour with Hey Riddle Riddle!...

#180: Best of 2021 - Part 2 29.12.2021

Did you think that we were just BSing about part 2 of the Best Of episode? Did you think that we would forget and accidentally record and produce a new episode instead? Well, we didn't! We remembered! And we have a bunch more of the Best Moments of 2021 for you. Yes, you, Jeremy. If you're reading this, Jeremy, know that we love you very much. You should quit your job at the bagel store and follow...

*UNLOCKED* Patreon Ep #137: HYAAH! Saddle Saddle! - Part 1 23.12.2021

FIXED! Happy Holidays! Here is a Patreon episode from a few months ago! Part 2 is also available now on our Patreon!  If you want to help support the show and listen to 100 + more of these eps, you can subscribe at Patreon   Well howdy pardners! Ya'll have been some mighty fine listens so here is part 1 of our Western series! We sure hope you enjoy part it! Grab your Stetson, smack a pigs ass and...

#179: Best of 2021 - Part 1 22.12.2021

We did it! We made it to the end of the year! Here are some of our favorite moments from 2021. If your favorite moment didn't make it-dont worry! We have part two of our best of episode coming next week. We appreciate your support this year and we think we will have a great time in 2022. See ya soon ya loons! Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey Toney Theme by:  Arne...

#178: … and Whatnot w/ Janet Varney 15.12.2021

Wow! She’s back! We are so lucky to be joined again by Janet Varney ( The JV Club and Avatar:Braving the Elements ) for some listener submitted word avalanche riddles! Stick around so you can hear the sun and the moon fight, a little girl who is a space genius, and a woman going on a date with some famous water! Let’s pee in the middle of the episode and have a great time! Starring: Adal Rifai Joh...

#177: EPISHODE! 08.12.2021

Grate nu epishode! We talk about thanking our future selves, one of us tries to (ahem) collect muppets, we explore the power of chickens, meet a unique sorority pledge AND Erin breaks the boys with the funniest goddamn story of all time! #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey Toney Theme by:  Arne Parrott Logo by:  Emily Kardamis  &  Emmaline Morri...

#176: Fanta Claus 01.12.2021

Happy December, Riddiots! We are kicking off the season right with the invention of a brand new seasonal character that we are sure to forget. Not only that, but we've got an awkward interaction at a front door, an unprepared student giving a report, a cocktail at a fancy bar, an IT professional fit for a queen, the unintentional invention of an existing property, and a kid embarrassed of their pa...

#175: Answer in French 24.11.2021

Happy day before Thanksgiving, everybody! We know you’re probably in transit to see some people you haven’t seen in awhile and you might be nervous. But don’t worry! We’ve got you covered. Adal and JPC have advice for any situation you might run into this weekend. The Clew Crew also does some listener submitted riddles and reinvents some classic literature. We probably make it worse-but we won't s...

#174: It's Doorpy!!! 17.11.2021

We get a little slap happy this episode and go on a deep dive of trying to figure out what the best combination of animals would be (accidentally inventing Pokemon along the way). There's also eyeball powers, a kitty doorman and we finally love riddles so much we marry them! Keep that bus at 55 mph and get ready to flex that brain! It's Hey Riddle Riddle! #WiddleWednesday Starring: Adal Rifai John...

#173: On Our Erin's Birthday? 10.11.2021

Today is the day, folks! Our very own Erin Keif (professionally known as Sharon Beef) is turning the big 3-0! And how are we celebrating her? Well, it's a riddle podcast so we'll probably be doing that. Is it a great birthday? No. But this is the real world. It's filthy and it's awful and every day is riddles (which we love) and that's just how it is. Oh, and we've got a lost cause who just might...

#172: The Riddle Floor 03.11.2021

It wouldn’t be Wednesday without some Riddles! This week we have riddles submitted by listeners, a chess funeral, and the return of Pretzel Jesus and JP Riddles. The crew crew also gets stuck on an elevator for 5 whole minutes. Then Erin remembers the date of a historical event and WILL NOT LET IT GO. Stick around for a conman barber and an incompetent sommelier. Have a great week! Starring: Adal...

#171: Bleh Riddle Riddle 4 27.10.2021

In our 4th annual Halloween episode; Adal deals with a troubling family issue, the gang debates what constitutes good candy, we all face our worst fears and there's some spooky animal parading, creepy riddles and at the last possible moment we sneak in a Rap For Daddy! Come up to the lab! See what's on the slab! I see you shiver....with....a distaste for riddles! #WiddleWednesday Starring: Adal Ri...

#170: Erin Goes to a Haunted House 20.10.2021

Look, we are going to do riddles on this episode. Of course we will. It's a riddle podcast. But really we are just here to hear about Erin's Haunted House experience. That's October for you. All that and we introduce the costume of the season, a professional trying to close a deal, a newspaper column that's just a little off, and a new neighbor with bad behavior. It's the spookiest month of the ye...

#169: Edward Splinterhands w/ Holly Laurent & Greg Hess 13.10.2021

On this week’s episode we have the incredible Holly Laurent and Greg Hess from the MEGA Podcast ! We’ve got penguin dads, birds in heaven, and a deep dive of McDonald’s toys. Stick around to hear Hamlet to chat to a skull and Greg gets to give us TERRIBLE news about Blue Man Group. All three HRR hosts have been on their podcast and had the best time so give it a listen! Starring: Adal Rifai John P...

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