Hey Riddle Riddle #385: I Want to Say Cookie Wolf?

Date: December 3, 2025
Hosts: Adal Rifai, Erin Keif, John Patrick Coan (JPC)
Podcast: Hey Riddle Riddle by Headgum

Episode Overview

In this lively and chaotic episode, Adal, Erin, and JPC, three Chicago improvisers, tackle a fresh batch of riddles, puzzles, “Animal Parade” word games, and hilarious improvised scenes. The episode is classic Hey Riddle Riddle—where the comedy greatly outweighs the riddles, digressions abound, and the trio’s signature chemistry and wit shine throughout. Amidst playful jabs, holiday banter, and riffs on cereal mascots, the hosts also discuss childhood snacks, creative Halloween handouts, and the absurdity of having sugar for breakfast—all while solving (and sometimes stumbling through) genuinely tough riddles.

Key Discussion Points & Memorable Segments

Banter & Holiday Stress (02:40–10:30)

• Physical Comedy & Concussions: JPC jokes about a black eye from Black Friday sales, leading to extended banter about concussions, fainting in public, and relatable health anxieties.

  "Do you think you've ever had a concussion, Adal? You played football, right?" – JPC (04:20)

• Travel & Thanksgiving Woes: The hosts discuss their disrupted holiday travel plans, canceled flights, and a potential mega road trip to Philadelphia due to an air traffic controllers' strike.

  "I'm quite worried because I will need to leave literally six days before tour starts." – Erin (09:51)

Social Commentary with Humor (12:13–13:18)

• Elections & Voting: JPC riffs on the state of democracy and how the “devoted few” would make up the electorate if Dance voting required ID, poking fun at both US elections and “Dancing with the Stars.”

  "Our democracy is in absolute tatters. Not really even a democracy to begin with, so just kind of a system of norms that turned out we're not very normed." – JPC (13:10)

Animal Parade Riddles Return (15:21–29:03)

• Introduced by JPC, this beloved game involves replacing well-known animal product mascots with similar-sounding rhyming counterparts or swapping parts of words.
• Cereal Mascot Rhyming Game (16:45–21:17):
  • Guessing new “rhyming” or slant-rhyming names for mascots, such as Smacks (the frog) with “jet packs,” and Cookie Crisp Wolf with a “charming lisp.”
  • Results in the episode's title when Adal improvises as the Cookie Crisp wolf:

    Cookie Wolf Origins:
    "My name is... Oh, no one's ever asked me. I want to say Cookie Wolf." – Adal (19:53)

• Scene: Adal’s wolf tries to entice Erin’s character to eat Cookie Crisp, all while riffing on the absurdity of cereal mascots intruding into daily life and, in this universe, “stealing moms.”

Childhood Snacks & Halloween Candy Philosophy (22:13–25:36)

• The hosts discuss restrictive snack rules growing up, the oddity of being pumped full of sugar as children, and the ethics of handing out candy for Halloween. JPC considers alternatives like Play-Doh and plastic spider rings for next year.

  "I feel very conflicted because around Halloween this year, I do not want to hand out candy because I don't like, condone the eating of candy." – JPC (23:26)

• Funny Neighborhood Traditions: Adal, Erin, and JPC joke about “Easter for Halloween” households who fill eggs with a mix of candy, toys, and actual cash, musing on how to brand oneself as the “wackiest neighbor.”

Animal Parade, Round Two (27:03–29:03)

• Second set of animal-mascot riddles (e.g., lion with a cane, kangaroo with a couch). The improv spins off into elephants wanting drinks after gestating for two years, and puns galore.

Rental Riddle Book Challenge (37:48–64:28)

• JPC introduces riddles from a physically curated “rental riddle book,” whose answers turn out to sometimes be confusing or incomplete.

• Tough word riddles include:

  • Riddle Example:
    "On your back or hold me in your hand. Break the former, a bill to demand. Break the latter, knowledge you'll land."

    The answer: “Spine”—as in spine of a book (knowledge) and breaking your back (medical bill).

• Scene Interludes:

  • Surgical scene (43:08–46:05): Adal about to get invasive spine surgery from a substitute “clown surgeon” (JPC).
  • Spelling bee sketch (52:48–56:02): Erin intentionally spells the wrong words, the judges get confused, peyote is involved.
  • God Scene (57:33–61:12): JPC is God after creation, Adal is his friend; riffs on “main/many/making” riddle answers, dinner reservations, and biblical family drama.

• Notable Quote:

  "What if we wrote 'please don't fuck my mom', but we just translated it into Japanese and then back to English, and then we did that like six or seven times." – JPC (40:15)

Riddle: "Middle" (61:36–63:38)

• A riddle referencing middle parts, the middle ear, and Middle Earth leads to:

  "The answer is middle. Oh, oh, oh. 'It just takes some time...'" – JPC, breaking into Jimmy Eat World lyrics (63:38)

Final Scenes & Plugs (64:36–67:41)

• Scene: Erin “falls into” Middle Earth and pesters an over-it Gandalf-type JPC; hosts reflect on restaurant etiquette.
• Show plugs: Quality Time (Erin), various podcasts (Adal), and new holiday-themed merch (JPC): “Smacks the frog please don’t fuck my mom” T-shirts and sweater episode merch.

Notable Quotes & Moments

• On Adal’s “Cookie Wolf” improv:
  "My name is... Oh, no one's ever asked me. I want to say Cookie Wolf." – Adal (19:53)

• On childhood sugar intake:
  "Isn't that insane to just be like, I ate marshmallows for breakfast. I ate 1.3 pounds of marshmallows for breakfast. Ready to learn." – Adal (22:13)

• Meta Comment on Recent Riddles:
  "These are horrible. They're all very hard. I believe in you guys though. You guys are some of my best guys." – JPC (61:12)

• Philosophy on women and elephants:
  "For every woman out there, elephant or not, I hope you die with a... smile on your face at the local watering hole." – Adal & JPC (29:13)

• On Halloween handouts:
  "There was a house in my neighborhood in Chicago that... would dress up in Easter wear... and have eggs [with] one Starburst or a five dollar bill in it." – Erin (24:56)

Timestamps for Important Segments

• Physical Comedy & Concussions – 02:40–06:15
• Holiday Travel Problems – 08:50–10:30
• Animal Parade Riddles: Cereal Mascots – 16:45–21:17
• "Cookie Wolf" Scene – 19:19–21:17
• Childhood Snacks Debate – 22:13–25:36
• Animal Parade, Round Two – 27:03–29:03
• Riddle Book Challenges Begin – 37:48
• Clown Surgeon Scene – 43:08–46:05
• Spelling Bee Improv – 52:48–56:02
• "God’s Creation" Improv – 57:33–61:12
• Middle/Seasons/Middle Earth Riddle – 61:36–63:38
• Middle Earth Scene – 64:36–67:12
• Plugs & Closing – 67:41–68:48
• (Skip ads: 00:05–02:40, 28:23–37:48, 31:51–37:48, etc.)

Tone & Language

The episode’s tone is fast-paced, whip-smart, and playfully irreverent—riff-heavy with relentless digressions and meta asides, and authentic to the hosts' Chicago improv roots. The language is casual, veering into the absurd, and sprinkled with inside jokes for longtime fans (“Smacks the frog please don’t fuck my mom!”).

Summary

This episode of Hey Riddle Riddle embodies the show’s best and silliest qualities: inventive riddles mingled with ridiculous improv, genuine friendship, sharp wit, and barely-concealed chaos. Whether they're pondering why we feed kids so much sugar or improvising as haunted cereal mascots and Old Testament figures, Adal, Erin, and JPC deliver another hilarious, unpredictable, and joy-filled hour—where the riddles matter, but not quite as much as the laughs.

For more:

• Hey Riddle Riddle Patreon
• Merchandise, including the infamous "Smacks the frog please don’t fuck my mom" shirt: heyriddleriddle.dashery.com