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

*UNLOCKED* - Patreon Ep 38 - Pubic Access TV! 03.01.2020

Here is another sneak peak of some of the fun you’re missing out on over on the Patreon! We have AT LEAST 50 hours of episodes over there so check it out! Thanks for tuning in! In today's Patreon episode we explore Public Access TV by creating our own possible shows based on existing show names! It's a wild ride and we don't apologize for any of our insanity. If people enjoy this we hope to do som...

#76: How Far Up The Egg Do The Pants Go? 01.01.2020

Another year in the books, can you believe it? Well, The Clue Crew is going to celebrate the only way we know how: with Riddles! And not just any riddles, some special riddle submissions from incredibly smart and good-looking listeners just like you! So join us as we cap 2019 and welcome 2020. Here's to 400 more years of this cursed podcast! Starring: Adal Rifai John Patrick Coan Erin Keif Editing...

#75: The Night Before Puzzmas w/ J.P. Riddles 25.12.2019

What better way to celebrate the Holiday season than with a clip show! While we would never claim that this is a "best of" (because the entire podcast is the worst), this is technically a best of J.P. Riddles (because everything he's done is the best). So enjoy a special Christmas story and then every clip featuring J.P. Riddles. And if you're curious, check out the earlier eps to hear much more t...

#74: Booty Butt 18.12.2019

We start by talking about our Chipotle orders and end with a Bond girl. All in a #Widdlewednesday! The three of us play for the bulls, Gollum tries to navigate his relationship, and we talk about a “bad word” that’s all the rage amongst Chicago youth. Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey Toney Theme by:  Arne Parrott Logo by:  Emily Kardamis  &amp...

#73: Sharkest Heart 11.12.2019

We're gonna need a bigger Riddle!! In this episode we have shark pop, truth telling hips and the hosts decide to get ripped as a bit! Throw some chum in your ears and get ready for a bite of Hey Riddle Riddle! #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey Toney Theme by:  Arne Parrott Logo by:  Emily Kardamis  &  Emmaline Morris W...

#72: Skull & Boneheads 04.12.2019

On this week's episode, we investigate why you should never do a favor for a family member, the importance of reading all the side effects of your medication and the pitfalls of unconventional domestic travel. We also talk pets, super hero origin stories, our favorite bands and re-casts of popular tv shows. Oh, and somewhere in there we might also accidentally do a riddle or two. Enjoy your #Widdl...

#71: Kid Friendly Episode (really!) 27.11.2019

For the first time ever, we have an episode that’s safe for kids. You can listen to this on the way to Thanksgiving with your children! You’re welcome! There are pirates, penguins, and a kid friendly JP Riddles. We also have a very special sandbox featuring Sandy’s son, Ezra. THERE IS A REAL KID ON THIS EPISODE!!!!  Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey Tone...

#70: Hundie Dollie Giveaway Returns! AKA Rap For Daddy! 20.11.2019

It's the return of Adal Rifai's Hundie Dollie Giveaway! This game show's got everything: One hundred dollars, questions, personal info, rapping! We also get some forbidden Canadian romance stories, a dried fruit vendor connection, the fall of the NCAA and the newest and coooooolest Star Wars character! Sing along to the theme, it'll be stuck in your head for weeks!! #WiddleWednesday Starring: Adal...

#69: Dirty Sexy Riddles 13.11.2019

Oh HELL yeah, it's episode 69 and you KNOW your boy JPC (30 year old man) has taken over the podcast feed! Adal and Erin NEVER let me write the episode descriptions but now the BIG DOG (150 lb weakling) is off the leash! So put a tarp down because this episode is a slip and slide. We talk about filthy stuff like sex and dirty stuff like doing it! Plus we've got mouth sounds, sock hops, celebrity c...

#68: The Birds, the Bees, the Nicolas Cages 06.11.2019

It’s Wednesday and Erin is reading some listener submitted Riddles. In this episode JPC marries rich, Erin goes to hell, and some birds go to burning man. We also do an impromptu game show and the competition gets heated! Make sure you listen long enough to hear three different Nicolas Cages talk to each other. If you want to send us riddles, email us at  hrrpodcast@gmail.com Starring: Adal R...

#67: Bleh Riddle Riddle 2! 30.10.2019

Night of the Living Dead Stop! It’s our second Halloween episode and we’re scared of how much terrifying content we packed into it! We have spooky riddles, the shocking return of J.P. Riddles, Halloween costume ideas and the answer to last years cliff hanger; WHO IS THE UGLIEST WOMAN!? Put a blood capsule in your mouth and get ready to bite down....it’s Bleh Riddle Riddle! #WiddleWednesday Starrin...

#66: On The Ground, In Disguise 23.10.2019

Well, we're off to the races with the return of our good friend Padraic Connelly's Anagram Riddles! By far the best riddles we get on the show and we completely ruin them with our usual BS! Take a detour into the world of Dr. Seuss, aging backwards, the prison-industrial complex, and our pitch to Sesame Street for a new character. And, as always, a review of popular chain restaurants! If there’s a...

#65: Watson Can You Hear Me? 16.10.2019

On this week’s episode, the crew visits a call-in-advice show that definitely doesn’t go as planned, debates the merits of war, turns espionage into an art form and travels across the pond to disastrous results! Plus the return of our Only Connect style riddles. It’s an absolute mess, so enjoy! #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  Casey Toney Theme by...

#64: The Purple Episode 09.10.2019

In this episode we pay homage to one of our all-time favorite bands with a brand new game that you're sure to hate! Plus we've got dogs on fire, a return to colonial times, Supermen in disguise, terrible accents and a visit from everyone's favorite character: Puzzbot! You're gonna love the way we Widdle, we Riddleantee it! #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif Editing b...

#63: A Pun in the Pool 02.10.2019

It's 63 and we're full of pun-energy! We read some riddles from loyal listeners and then verbally dismantle them then go back to one of our least favorite riddle books! We're talking about inventions, circuitry, cocktails, baseball, new twists on classic comedy bits and an ill-fated attempt to run for Mayor of Indianapolis. This episode is insane and you're all our puppets! Keep your moms away fro...

#62: Hey Riddle City Part 2! 25.09.2019

The Clue Crew wades back into the black and white depths of Riddle City. Brick Stoneheart and Mickey Rourke (no relation) will stop at nothing to solve their case, but was locking up Coco Cashmere the right thing to do? Probably right? That voice? Listen as Erin parades out several more colorful characters to populate the 1940's world that is... RIDDLE CITY! ...PART 2! #WiddleWednes...

#61: Fun At Songs! 18.09.2019

Hard to believe we're in our early sixties! This episode brings a 'Him's A Ghost' tv pilot, gas station t-shirt creations, a bunch of shout-outs to Seattle, all the celebrity death news you could want plus child tattoo's and jaded Transformers! Oh also Erin tries to get us to guess her email password which she wants you to also do but probably not? Annnnd Sandy swings by for a bit of summer f...

#60: Floor Soup! 11.09.2019

Attention Riddle High Students! This episode contains chair talk, snakes on a plane, founding father 'raps', even MORE J.P. Riddles and the introduction of our favorite new segment: Erin's Animal Corner! Grab a stool, face your bed and watch your spouse listen to this weeks Hey Riddle Riddle! #WiddleWednesday #chairtobestupid Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  KJ Sn...

#59: That Sucks! That Rules! 04.09.2019

The crew is a bit slap-happy in this one! We do some Amelia Bedelia riddles, hear Erin start using water for some Foley Artistry (DO NOT LISTEN TO THIS EPISODE IF YOU HAVE HYDROPHOBIA), find out there's a new mustard in town, get a sample of Songs Of The Salt 80's and you better believe we fire allllll the butlers! Erin is a saint and her least favorite movie is Girl Interrupted. #WiddleWednesday...

#58: Flirty Chef! 28.08.2019

The Clue Crew hasn't recorded in a bit so we catch up on our lives and play a new game fit for a chef (which leads to a VERY special Dead Stop)! We also disagree with what bedroom posters are fit for children, suss out the best 'ships', visit the barber, have some Broadway blunders and figure out America's best kept secret on how to get rid of trash! We're 58 and feeling great! #WiddleWednesday #C...

#57: The Question Is The Answer! with The Teachers Lounge 21.08.2019

It's our final Hollywood Nightz episode and it's special as hell! We celebrated with one of our favorite podcasts The Teachers Lounge! Featuring Dan Lippert, Jon Mackey and Ryan Rosenberg (@BigGrandeUCB)! We parse through breakfast foods, play a shitty game of Catan, name our kids, make weird bets, get the ol' catholic discount at a bar and end with some unconventional romance! Check out season 8...

#56: Hey Riddle City! A Pod Noir, Part 1 14.08.2019

What's black and white and rid(dles) all over? Why it's Riddle City see! Erin Keif (the hottest dame in town) takes us to a dimension of her own making with Riddle City! Join detectives Brick Stoneheart and Mickey Rourke (no relation) as they try and solve a mystery while interrogating all the colorful characters this booze soaked episode has to offer. Forget it Japes...It's Riddle City...Part 1!...

#55: Just Plain Comedy! 07.08.2019

After 55 episodes we finally decide to lock in some nicknames for each other! We get a new round of jokes for kids, hear the worst High School assembly ever, talk shoplifting and bring in our favorite Cookie Man, Sandy Weisz, for a brand new Sandbox! #WiddleWednesday Send us emails at  hrrpodcast@gmail.com Starring: Adal Rifai John Patrick Coan Erin Keif Guest Starring: Sandy Weisz  at&n...

*UNLOCKED* - Patreon Ep 18 - Hey Relationship Relationship 01.08.2019

We wanted to share with you one of favorite Patreon episodes of the year! This is Patreon episode #19 where The Clue Crew steps out of the studio and let some EXPERTS take over! Fledorious Plomp, Felix Missingson, and Beverley Condolences are three relationship experts with their own talk shows on love. They answer questions about bad habits, parenting, and when to tell the truth. If you’ve got a...

#54: A Star Is Wars! with Jeffrey Cranor 31.07.2019

In our penultimate Hollywood Nightz the brilliant Jeffrey Cranor (Welcome To Night Vale, Within the Wires, Start With This) joins the Clue Crew with some puzzies of his own! We talk rental car woes, crossword puzzle streaks and the what state you'd most want to bang! We also have some wealthy fights, quiet animals, young ass vampires and a new serial killer on the loose! Welcome To NOON Vale! It's...

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