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Hey Riddle Riddle

Podcasts · Leisure

Hey Riddle Riddle

531 episodes · 20 with AI analysis

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

AI Intelligence · across all analyzed episodes

People · top 20

Companies · top 20

Topics · top 10

Podcast sponsorship integration×3Podcast audience engagement strategies×2Riddle solving and lateral thinking puzzles×2Subscription management and financial tracking×2Small business financial management×2Sustainable fashion and wardrobe building×2Small business financial management platforms×2Riddle solving and lateral thinkingChicago local history and urban legendsSpeech pathology and childhood impediments

Analyzed Episodes

Apr 15, 2026

#404: Episode Not Found

Riddle solving and lateral thinkingChicago local history and urban legendsSpeech pathology and childhood impediments

Apr 10, 2026

Patreon Preview #370: Penguin Baseball Draft Season Three w/ Janet Varney & Casey Toney

Fictional sports league draftingMythical creature worldbuildingImprovisation comedy structure

Apr 8, 2026

#403: Nobody's in Charge

Riddle solving and lateral thinking puzzlesImprov comedy scenes and character workChicago winter weather and frozen pipe repair

Apr 1, 2026

#402: Imagining a Dune Buggy w/ Janet Varney

Animal Pun Riddles and WordplayReality TV Analysis - Dance MomsImprov Scene Work and Comedy

Jan 23, 2026

Patreon Preview #359: Welcome to New Hampshire 🥾

New Hampshire state motto and libertarian valuesNew England regional comparison and tourismState laws and legal oddities

Mar 27, 2026

Patreon Preview #368: Who Wants to be a JPCillionaire? Part 2

Game show parody formatTrivia competition mechanicsPodcast prize structures

Mar 25, 2026

#401: Goodfella's But They're In Love

Comedy improvisation and game-based podcast formatsPatreon monetization strategies for podcastersWord puzzle game design and mechanics

Jan 28, 2026

#393: Mr. Mouse Bones

Film criticism and movie appreciationGuy Ritchie filmography analysisInternational idioms and language translation

Jan 30, 2026

Patreon Preview #360: Improv Starters

Improv scene structure and character objectivesTeen-parent conflict scenarios in improvisationBook organization and content curation

Mar 13, 2026

Patreon Preview #366: The Apocalypse Draft

Apocalypse fiction and end-of-world narrativesAlien occupation scenariosZombie apocalypse tropes

Mar 20, 2026

Patreon Preview #367: A Night at a Museum

Museum night lock-in eventsHidden treasure hunts and scavenger huntsMuseum docent roles and responsibilities

Mar 18, 2026

#400: A Most Puzzling Season

Riddle and wordplay mechanics in entertainmentRegency-era social customs and courtship ritualsCharacter-driven comedy writing

Feb 4, 2026

#394: Jokes We Don't Get

Riddle and joke book analysisImprovised comedy scene workVintage humor from 1870s-era riddle collections

Feb 6, 2026

Patreon Preview #361: Reacher for the Stars

Lee Child Reacher novel series analysisEcho Burning plot summary and themesAbusive marriage narrative in crime fiction

Feb 11, 2026

#395: Peep Impact

Seasonal Candy Marketing and Consumer BehaviorChild Labor Practices in Classic HollywoodRiddle Construction and Misdirection Techniques

Feb 13, 2026

Patreon Preview #362: Summer on Scorn Mountain

Fire prevention and monitoringRemote work isolationSmall business financial management

Mar 11, 2026

#399: Tedd-99

Comedy improv and sketch writingPodcast audience engagement strategiesRiddle and word game design

Mar 6, 2026

Patreon Preview #365: Who Wants to be a JPCillionaire?

Who Wants to Be a Millionaire game show format and historyGame show lifelines and strategic decision-makingJohn Carpenter's million-dollar win and cultural impact

Feb 18, 2026

#396: We Smabi

Greeting conventions and social communicationRiddle solving and lateral thinking puzzlesCultural knowledge through comedy and parody

Feb 20, 2026

Patreon Preview #363: Chatterbox 32

Parenting strategies and child behavior managementSeasonal food products and consumer preferencesSmall business financial management platforms