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

#53: It's Been...ONE YEAR! 24.07.2019

Bingo Bango! It's our one year anniversary! We reflect on the year that's been and look forward to what's next while of course doing some riddies and puzzies along the way. How do you best dispose of Mad Cows? What's it like to have a phone call with the Queen of England? Can anyone survive playing poker with their family? How hard is it to be an announcer at a basketball game? We don't come close...

#52: Body Magic! 17.07.2019

We're doing some listener submitted riddies and puzzies while trying to remember what improv is! Boy oh boy are we craving the weird colorful mash from Hook, most vegetables and some very specific brands of pizza! In this episode you'll get a sneak peak into JPC's acting class and enjoy James Bond, pirates and fairies. We also have the triumphant return of our brainy ass bud Sandy Weisz with a tas...

#51: JANETMORPH! with Janet Varney! 10.07.2019

How do we follow up the madness of episode 50?! By having one of our favorite humans on Earth co-host! It's HOLLYWOOD NIGHTZ part 3 and we get silly.as.hell with the incredible talent that is Janet Varney (The JV Club, Voyage To The Stars, Legend of Korra)! We talk Animorphs, take a sneak peak into the inner workings of British Parliament, pontificate on the Kool-Aid Man, play a round of CLUE and...

#50: Fifty Riddles GUARANTEED! 03.07.2019

How did we get here?! It's episode 50 and to celebrate we are doing fifty riddles in just over an hour. Some said it couldn't be done! Join us in this mad dash against time as some of our favorite characters, guests and collaborators pop on to wish us... well I don't know if they really wished us anything, but we have lots of fun surprises in store. Even if you never listen again, you're GOING TO...

#49: Carrot Bottom! 26.06.2019

Welcome to Juuuune! In this episode we enter a Spelling Bee, preemptively bust Tiger Woods, create the best Horny Snack and put the worst roommates on blast! Don’t bother remembering the pledge of allegiance, it’s Hey Riddle Riddle! #WiddleWednesdayStarring: Adal Rifai John Patrick Coan Erin Keif Editing by:  KJ Snyder Theme by:  Arne Parrott Logo by:  Emily Kardamis  &&nbs...

#48: Boat Detective with Hayes Davenport! 19.06.2019

Uh oh! Someone posted our 2nd HOLLYWOOD NIGHTZ episode with special guest Hayes Davenport (Hollywood Handbook, The Flagrant Ones) and things get a lil wild. From Houdini being totally prepared to meet a fan, the Christmas jug finally being celebrated and the drama we've all been yearning for, a detective partnered with a talking boat. We also get a Michelin review of Rainforest cafe, Erin finally...

#47: Pyramid-Life Crisis! 12.06.2019

We start off with some jokes for kids (not suitable for actual kids) before detouring into some Swan Lumps, old-timey war letters and a Droid Road Trip! The Clue Crew also visits a child prison (not suitable for actual children), explore what it means to be a car owner in Florida and dive into the mirror/princess reality that most fairy tales are afraid to show you! #WiddleWednesday Starring: Adal...

#46: It Came from the Basement! 05.06.2019

We're drowning in books thanks to our 'thoughtful?/spiteful?' fans. In this episode we start to chip away at the onslaught of Stories With Holes. We meet a committed stripper, audition for animated buttons, hear Erin's new romance novel and dry off all the dead dogs you can shake a stick at! Don't go into the basement.....for it's Hey Riddle Riddle! #WiddleWednesday Starring: Adal Rifai John Patri...

#45: Lucky Songbird! with Jon Gabrus 29.05.2019

It's here! Our first of many HOLLYWOOD NIGHTZ recordings to come; with special guests we had on in LA! We kick it off joined by the wonderful Jon Gabrus who along with the Clue Crew helps discover the extra sins left on the cutting room floor, lays down the law as a kid boss, finds new terms for being horny and embraces his inner Long Island English Teacher! You're gonna get the dirty swirls liste...

#44: Adal's $100 Give Away!!! 22.05.2019

Uh oh! Uncle Adal's got his check book out and he's made a brand new game show for JPC and Erin to play! You better believe there's real money up for grabs AND a theme by Arne Parrott! JPC can't stop giving killer middle names and Erin motivates herself to continue to play! Plus we attend a Patriots game, meet a drug dealer to the stars and wash ashore on a famous island. Be ready to Puzz in with...

#43: He's Mimble!!! 15.05.2019

This episodes got it all! 1. A new name for our listeners 2. A new tv show on we created 3. A public service commercial for PAWS 4. Billie Jo Armstrong's real height and Nelly Furtado's too real life! 5. We have all new bespoke riddles created by our friend Pad Connelly! Listen, laugh, love us and hate riddles. #WiddleWednesday Oh also 6. We sing way too much in this. Starring: Adal Rifai John Pat...

#42: Post Potatoes! 08.05.2019

Slap happy as hell, we discuss the ins and outs of starch, pick on a substitute teacher, explore the origins of the name Keif on Ellis Island, rank the best candy to receive and you BETTER BELIEVE Adal & JPC debut their new lounge act! Get tickets for our May 12th live show in Los Angeles at  www.headgum.com/live  #WiddleWednesday  Starring: Adal Rifai John Patrick Coa...

#41: Dr. Funny Comedy 01.05.2019

Paging all Kevins and Susies! We reluctantly step into another batch of our favorite riddles and thereby enter a clown realm of madness! The gang also promotes a new cereal, redefines what cardboard can be and has a sincere conversation about the emotional consequences of lifting up one person by tearing down others....we swear this is a comedy podcast! #WiddleWednesday Look for tickets to our upc...

BONUS - AMA Special 29.04.2019

You gave us 1000 five-star reviews so we're giving you our first ever bonus AMA episode! Find out all the sweet sweet personal info you wanted to know about us and also some real goofy stuff! We only got through about 20 or so questions so we'll do another AMA release once we hit 1500 five-star reviews. Don't forget to grab tickets to our live show in Los Angeles on May 12th, tickets at  http...

#40: All Sherlock! 24.04.2019

Deduction! Elementary! Egads It's a special themed episode with some characters that resemble those from Arthur Conan Doyle's epic books but are definitely way younger and cooler! We get to see two moths on a first date, meet the great 90's Hip Hop group that wasn't meant to be, and sit through the most awkward 5 minutes of stand up ever performed! Grab dem magnifying glasses and play your violin...

#39: Horse Court with TJ Jagodowski! 17.04.2019

The ever brilliant TJ Jagodwoski joins us for some puzzie solving tomfoolery including some Mass. chat, a look at mermaid parenting and putting a horse on trail for GOOD REASON. Also we're coming to LA in May and doing a show at home in Chicago in June! You can buy tickets here:  https://headgum.com/live  and also check out our Patreon if you'd like to double your weekly dose of Adal, Er...

#38: The Great Butterbeer Showdown! 10.04.2019

It's a competition between Erin and JPC to see who gets a free drink! We talk theme parks, Ribfest sexuality and cake v. pie! Enjoy us trying to remember Captain Planet, listen in on Erin having a meltdown and learn that it's never too late in life to invent flight. Rate and review us on iTunes to help get us to 1000 5-Star reviews and we'll release a bonus AMA episode! Yum Yum it's #WiddleWednesd...

#37: Raccoon Penis Bone! 03.04.2019

There's a whole lot of dumb.ass.fun. happening when someone get's LASIK in an unexpected place, we pick out our DJ names while crafting the first ever cousin dance floor banger, Erin legit thinks she can get voted into the Rock & Roll Hall of Fame and we see the return of everyone's favorite sociopath... J.P. Riddles! #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif Editing by...

#36: Dear Diary... 27.03.2019

We write down all our secrets & feelings in this new episode plus we launch into a scene in record time! Also JPC and Erin brag about dating people who live in buildings, Adal dies on Sandra Bullock hill, we celebrate a well known 90's toy and end with figuring out if a certain celebrity would ever date Erin and if a certain celebrity propositioned Adal! #WiddleWednesday Starring: Adal Rifai J...

#35: JUST Trains & Automobiles 20.03.2019

The Clue Crew is allllll aboard for this episode featuring mostly modes of transportation! JPC provides some Sorting Hat action, Adal doesn't understand what it means to be a lifeguard and Erin is Les Miserable! You better believe Sandy Weisz brings us a new Sandbox! Beep Beep! Out of the way! It's time for a road trip with Hey Riddle Riddle! #WiddleWednesday (New merch is now available at  h...

#34: The More You Know! 13.03.2019

After the fateful return of the 'Your Spouse' segment and reminding ourselves what the show is; the Clue Crew is whisked back in time to 1993! Adal reads from the first riddle book he bought from Scholastic, Erin gives us a deep dive into her 'realm of pillows', and we maybe find out what JPC really stands for? We also make some long overdue PSA's for a very important subject! #WiddleWednesday Sta...

#33: The One With The Most! 06.03.2019

An episode JAM PACKED with the most Riddles we've ever done?! Erin is given a mysterious box full of puzzles and makes Adal & JPC do as many as humanely possible in this potent potent episode! Rumors abound about what Erin drinks! We introduce HRR Nights! and you better believe there's some audience homework! MOST RIDDLES EVER! #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif...

*UNLOCKED* - Patreon Ep 1 - State...Yo Business! 01.03.2019

As a special treat we're dropping our first Patreon episode in the regular feed for folks to check out and hear what they're missing! In this one Adal tests Erin & JPC on their state knowledge, specifically for Indiana and Mass.! I'm sure we offend the residents but it's too late! It's already recorded! If you enjoy this episode please consider subscribing to the Patreon to receive bonus episo...

#32: LOST Boyz! 27.02.2019

Adal & JPC finally tie the knot, Erin reveals terrible eating habits and the Clue Crew is dealing with a lot of kids and Peter Pan in this episode for some reason! We dole out some bank robbery advice, recall all the big news of 1996 and decide which Muppets we are! #WiddleWednesday Starring: Adal Rifai John Patrick Coan Erin Keif Editing by:  KJ Snyder Theme by:  Arne Parrott Logo b...

#31: Take a Riddle Bit Off the Top! 20.02.2019

Adal introduces a new segment that's sure to become a staple of the show, Erin gets an unexpected call from a famous game show host who's still in love with her, and JPC attempts to join the Spice Girls! All this and we talk shop (barber shop), words with no vowels, month long parties and the Clue Crew recalls the best way to kill a Sim! Starring: Adal Rifai John Patrick Coan Erin Keif Editin...

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