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

#122: Rebel With A Cause! with Jake & Amir 18.11.2020

We're on our best behavior because we have our Network Daddies, Jake & Amir (CollegeHumor, If I Were You, founders of HeadGum), on the podcast and they're thirsty for answers! We invent some famous musicals, snag some BBQ at DinseyWorld, go to musical camp and meet the saddest insects in nature! Enjoy and if you have a chance, check out The Clue Crew guesting on a recent episode of Jake &...

#121: Pizza Talk Chony 11.11.2020

We have a grande riddle podcast for Riddiot. Is there a Riddiot in the house? This episode has two pumps of comedy and whole jokes? Anyone? Well, if no one claims it, then this podcast could be yours! All that and you get two best friends going through a tough time, a family trying to understand who they are, the happiest day of someone's life ending in terrible tragedy, a restaurant where you sho...

*UNLOCKED* Patreon Episode 72: Quiz Bop 06.11.2020

Here is episode 72 from our Patreon. We hope it's a good distraction! Oh no! The Clue Crew has filled their ear holes with cursed music from demon children and now it's time to pass that curse to you in our very own Kidz Bop Quiz! Can YOU find the real lyrics? Please, go watch some Kidz Bop music videos and let us know what you think. Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey...

#120: TWO Harmonica Solos 04.11.2020

Look over here! A shinny distraction! This episode has so much to occupy your brain. We’ve got listener submitted riddles, a horse on a date, a portal to hell, and the worst musical/play mash up of all time. Also Erin finally has a meltdown- it only took 120 episodes. Happy Birthday! I’m sorry! Happy Anniversary! Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey To...

#119: Bleh Riddle Riddle 3! 28.10.2020

It's our 3rd annual Halloween episode! We talk about how to trick r' treat in 2020, what all the hottest costumes are and uphold some Hey Riddle Riddle traditions! You'll hear a clown robbery, get to know who exactly is in Damages and play along with a spooky version of your favorite $100 Giveaway! Drink some fake blood, eat a tiny snickers and lay down to enjoy the scariest podcast of the year! #...

#118: Slamlet 21.10.2020

"To puzz or not to puzz, that is the riddle." On today's episode, we ponder the work of the great bard Billy Shakes but guess what? We make it fun! All that and we take a tour of the greatest city in the world with some of the worst people on the planet, a rip-roaring re-telling of a spiritual touchstone, a gathering of some of the most famous scientific minds of their time, a dastardly villain wi...

#117: HARcut 14.10.2020

Wow! It’s Wednesday! I hope you’re in the mood for listener submitted puzzles- because that’s what we’ve got. We also have a one man haunted house, an embarrassing pharmacy visit, and a dad who can’t change a tire. Erin also learns that Brett Michaels and Kid Rock are different people. Can’t wait to read some hey riddle riddle fan fiction( please don’t write it)! Starring: Adal Rifai John Patrick...

#116: Three Butlers Living in the Very Same House 07.10.2020

This episode has everything you could possibly want in an episode of Hey Riddle Riddle: an out-of-context cold open, new nicknames for the hosts, a segment about showering and an impromptu sitcom. Truly it's one for the ages. Oh, and it's also got a budding romance between an unlikely pair, two protectors standing up for the peasantry, pedantic conversation at a somber occasion, an enterprising au...

#115: Bug! with Mary Holland 30.09.2020

Give me an H! Give me an R! ...uh I guess two R's actually?! What does that spell?! A GOOD TIME! We do our Riddle routine with the most popular girl in school, Mary Holland (Wild Horses, Comedy Bang Bang, the upcoming movie Happiest Season)! In this episode we strike a chord with our music teachers, meet a cursed neighbor, audition to be villains, call out great white sharks for what they really a...

#114: Carl Talk 23.09.2020

Hello Wednesday! How are you? We start this week by talking about some improvements we’ve made to our homes then we get into some listener submitted riddles! We mostly focus on giving some advice to a six year old. Spoiler- We aren't qualified. There is also a family snowball fight, an elaborate nighttime routine, and a very cautious princess. We hope you’re having a great week! Bok-quock quock! (...

#113: Auto-tune Bird Sounds 16.09.2020

The Clue Crew is back with another unhealthy dose of riddle nonsense. This one's got everything: instant applause breaks, a Canadian Moses, Adal finally standing up for himself, JPC finally standing up for his nose, and Erin celebrating the turn of the leaves! All that plus a brand new segment that you're sure to enjoy. It must be #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif E...

#112: Riddies & Daddies 09.09.2020

This week we are joined by special guests Freddie Wong, Beth May and Will Campos from The Dungeons & Daddies Podcast! If you're a fan of both shows, you're in for a treat and if you are only a fan of one show, you're about to have a new favorite podcast. Plus we some unintended magic, a pugilist of the avian variety, three birds of a feather digesting their own fate, a brand new due for a very...

*UNLOCKED*-Hey Riddle High: Get Bent! Part 1 07.09.2020

This is part one of our newest riddle city story! We are only releasing PART 1 on the main feed. Part 2 and 3 are available RIGHT NOW over on our Patreon. Go to Patreon.com/heyriddleriddle Welcome back to Riddle City! This time it’s 1985 and at Riddle City High. This THREE part series follows head of the school newspaper, Kyle Stoneheart and his new friend, Flint. The boys try to find the mis...

#111: The Heart is the Greatest Weapon 02.09.2020

Happy Wednesday! This week Erin is Old Man Puzzles and she reads some very creative listener submitted riddles. But that’s not all! There’s a man who doesn’t realize his son is a rat, a woman pretending to be a duck, and Rube Goldberg trying to propose marriage. We also see a commercial for a family owned mortuary that goes just as well as you expect. Is this week that we finally go insa...

#110: Don't Matter to Me, Broccolis 26.08.2020

On today's show, we are talking swim up basements, pop music, and personal interactions. All that and a boy learning about his past and what might be his future, an iconic pitch session for one of our favorite products, young love blossoming in a cold, cold place, two fruits from different paths, 10 screwballs who can't catch a break, the drama of a midnight sky, waxing poetic with one of history'...

#109: Dollar Signs & Question Marks! 19.08.2020

In this episode we're cooking with fire baby!...vs. cooking with....not cooking? We got some wild life updates (Assassins?!), some hot bedroom talk, a lesson on Macro Economics, some panning for gold, stoned pontifications and a Daniel Day Lewis debate! Put your tray tables up and keep an eye on your dog, it's Hey Riddle Riddle!! #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif Ed...

#108: We Also Make The Ducks 12.08.2020

We can't believe it's Wednesday! Again?! In this weeks episode we do listener submitted riddles and talk a lot about Ben Folds. We see a vampire stealing accents, a banana on a date, and Jeeves the butler help you find what you're looking for. Don't worry we also listen in on some bears waking up from hibernation and some men deciding who gets to walk on the moon first. We promise there is no monk...

#107: Tell Me Something, College Boy 05.08.2020

On this weeks show we can't stop horsing around or referencing decades old reality TV. All that and we see a man in a very compromising position, a romantic evening with a rock legend, a heartwarming moment and a mysterious revelation, a trip to a more simple and brutal time, and a master chef who knows exactly what he wants. We want to suck your drums! Happy #WiddleWednesday Starring: Adal Rifai...

#106: OH YEAH! 29.07.2020

Who just burst through your wall? A new episode! We're filled to the brim with clown talk, orphan advertisers and a new warm-up segment called Slogan's Run! We also discuss our favorite jingles from childhood, take a twisted look at The Little Mermaid and invent several new types of Santa! #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey Toney Theme by:&nbs...

#105: Milk Store with Geoffrey James and Reilly Anspaugh! 22.07.2020

Everyone start cleaning the house-we have guests! The delightful hosts of Review Revue, Geoffrey James and Reilly Anspaugh, are here! You can find this fellow Headgum podcast wherever you find podcasts! We can’t recommend it enough! In this episode we have gambling, rambling letters, vampires and JP Riddles. There are some audio issues in this episode! Just a heads up. Starring: Adal Rifai John Pa...

#104: The Baron, The Countess and The Fool 15.07.2020

One of our own joins the ranks of nobility and there is cause for celebration! Don't worry, the title change doesn't make us any less excellent at solving riddles. We also see an unlikely couple finding love in an unlikely place, the resurgence of one of our nation's finest businesses, the last and finest moments of two soulmates, nature's ability to heal, and some roadside assistance. All that an...

*UNLOCKED* Patreon Ep #61- Face to Face...Not! 10.07.2020

We hope everyone is staying safe and practicing social distance during this global pandemic. To help with sanity we have unlocked yet another episode of INSANITY from the Patreon. We hope you have a great weekend! Also if you want to help support the show and listen to 70+ more of these episodes, including video streams, D&D campaigns and more you can subscribe at Patreon.com/heyriddleriddle F...

#103: Tux On Top. Diaper On Bottom. 08.07.2020

Hey Ridiots! Papa Log in the fireplace because Adal is Old Man Puzzles and we have some Hink Pinks, an Animal Parade and a few other surprise segments! I know you're asking yourself what's in it for me if I listen?? Well, we've got Tango lessons, breakfasts that bully you, A WimbleTon match and our own spin on having a wild night in Vegas! Sing it with us...'He was a GREAT BIG MOOSE!' #WiddleWedne...

#102: We're Buying the Knicks 01.07.2020

Good morning, Riddlers! This week Erin is Old Man Puzzles so we’re getting some excellent listener submitted riddles! We ask some important questions like: Are we ruining Hollywood? Who was famous in the 1940s? Are we hurting our future children? There is also a discussion about an Entourage remake and a new (and improved) Mt. Rushmore! We love #WiddleWednesday! Starring: Adal Rifai John Patrick C...

#101: All The Mimosas You Can Carry 24.06.2020

We are fresh off our 100th episode bringing you that Riddle content you know and love! If you thought we were going to do some kind of reset to re-introduce the show and bring in more listeners, boy-oh-boy you've got another thing coming! Mixed into today's hilarity we explore a dirty movie set, an even dirtier profession, a brand new super villian, a cold treat to beat the heat, some family dynam...

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