Hey Riddle Riddle Podcast Episode #359: "Serving Grant!"

Release Date: June 4, 2025
Hosts: Adal Rifai, Erin Keif, and John Patrick Coan
Platform: Headgum

Overview

In episode #359 titled "Serving Grant!," the trio from Chicago—Adal Rifai, Erin Keif, and John Patrick Coan—delve into a blend of historical anecdotes, humorous takes on presidential trivia, spontaneous riddles, and improvisational skits. While the podcast's description hints at a focus on riddles and puzzles, this episode primarily showcases the hosts' comedic chemistry and creative improvisation, interspersed with light-hearted discussions about U.S. Presidents and quirky scenarios.

Historical and Presidential Humor

The episode kicks off with a playful discussion centered around U.S. Presidents, particularly focusing on the 25th President, William McKinley. The hosts humorously explore McKinley's assassination and the dubious medical practices of the time.

• Adal Rifai [00:56]: "Aaron, I wouldn't have guessed this, but when I saw it, it makes sense. Would you believe it's McKinley?"

• JPC [01:38]: "McKinley was the one who absolutely would have lived from that bullet. And they kept him alive for like two months."

The conversation humorously speculates on the absurdity of feeding assassinated President McKinley through unconventional means, reflecting on the limited medical knowledge of the early 20th century.

The hosts then shift to a playful critique of presidential portraits, imagining clandestine scenes where presidents might have posed comically or unofficially.

JPC's Haircut

A recurring humorous subplot involves JPC's newly shaved head. The hosts explore the unexpected sensations and practical implications of his bald look.

• JPC [05:17]: "I shaved my head, and it feels much sweatier than it did before... I can notice my head sweat, and I'm like, oh, wow."

• Adal Rifai [06:16]: "Does hair absorb sweat?"

• JPC [06:25]: "Yeah. Because, like, people's hair gets, like, stinky when they sweat."

This segment combines observational humor with exaggerated personal anecdotes, highlighting the quirks of JPC's new hairstyle.

The New Pope: "Chicago Pope"

Introducing the concept of the "Chicago Pope," the hosts draw humorous parallels between the papacy and iconic characters from popular culture, notably from the "Star Wars" universe.

• Adal Rifai [10:16]: "He's gonna be on Devil's Daughter if he got put on a team."

• JPC [17:27]: "I might join the rebellion. I might put the pussy hat on and be like, it's time to go to Yavin 4, everybody."

The discussion satirizes the grandeur often associated with the papacy by comparing it to fictional emperor figures, blending religious titles with sci-fi references for comedic effect.

Riddles Segment

True to the podcast's thematic roots, the hosts engage in a series of riddles, challenging each other's wit and creativity. These segments are interwoven with improvisational skits that visualize the answers in humorous scenarios.

1. Riddle: A candy store, a fancy hotel in Tchaikovsky. They all have something in common. What is it?
   Answer: Sweets (sweets as desserts or treats found in these places).

   • Adal Rifai [21:54]: "It's all about sweets."

2. Riddle: Football playbook, a love letter, and Hollywood Squares' Xs. What do they have in common?
   Answer: Squares or X's and O's.

   • JPC [28:53]: "Louie Anderson."

3. Riddle: A ladder, a mountain, a fish. They all share something in common. What is it?
   Answer: Scale (ladders and mountains can be scaled; fish have scales).

   • Adal Rifai [40:34]: "They are all things that are scaled."

4. Riddle: Eggs, bricks, carpets. They all have something in common. What are the two fruits?
   Answer: They are all things that are laid (eggs are laid by birds, bricks are laid in construction, carpets are laid on floors).

   • Adal Rifai [47:36]: "They are all things that are laid."

5. Riddle: What type of transportation has 10 wheels but can only carry one person?
   Answer: Rollerblades or Inline Skates (typically having five wheels on each blade).

   • Adal Rifai [59:53]: "It is rollerblades or inline skates."

Each riddle is accompanied by spontaneous skits where the hosts act out exaggerated scenes related to the answers, enhancing the comedic value and engagement for listeners.

Improvisational Skits and Scenes

Between riddles, the hosts create impromptu scenes that bring the answers to life. For instance:

• Post-Scale Riddle:
  Adal Rifai [40:50]: "These are all things you scale."
  They transition into a mock interview with a fictional character climbing Mount Everest as a fish, blending absurdity with the riddle's answer.

• Eggs, Bricks, and Carpets Riddle:
  Adal Rifai [47:52]: "Let's do a scene where JPC and I are interviewers, and you're the first fish to climb Everest."
  This leads to a humorous press conference scenario where the fish (played by JPC) discusses the challenges of climbing a mountain, further emphasizing the playful nature of the podcast.

These skits not only entertain but also provide a vivid, humorous portrayal of the riddles' solutions, making the content accessible and enjoyable even for those unfamiliar with the podcast.

Parodied Advertisements

Staying true to their comedic roots, the hosts craft spoof advertisements for fictional or exaggerated products, blending satire with playful promotion.

1. Tempo Chef:
   A fake meal delivery service boasting absurd features like "soup enemas" and unrealistic culinary claims.

   • JPC [33:46]: "Tempo serves up fast. Feel good single serving meals that are crafted to cook in just three minutes."

2. Quince Dresses:
   A satirical take on fashion brands, highlighting over-the-top features like "quince dresses that spin" and mock-practical concerns about hair.

   • Adal Rifai [35:02]: "Quince.com/riddle offers free shipping and 365-day returns."

3. Squarespace:
   A humorous promotion for website building platforms, interlacing jokes about personal mishaps related to the service.

   • Adal Rifai [37:26]: "Visit squarespace.com/riddle for a free trial and save 10% off your first purchase."

These segments are designed to mimic real advertisements, adding a layer of satire that critiques consumer culture while delivering laughs.

Conclusion and Promotions

As the episode wraps up, the hosts provide updates on their upcoming tours and encourage listeners to support them via Patreon.

• Adal Rifai [67:00]: "Check out our Patreon at patreon.com/heyriddleriddle and join the Clue Crew for exclusive bonus episodes."

• JPC [67:26]: "Our Twin Cities shows are dangerously close to selling out. Grab your tickets soon!"

The conclusion maintains the episode's comedic tone while effectively promoting the podcast's community and live events.

Notable Quotes

• Adal Rifai [00:56]: "Would you believe it's McKinley?"
• JPC [01:38]: "McKinley was the one who absolutely would have lived from that bullet."
• JPC [05:17]: "I shaved my head, and it feels much sweatier than it did before."
• Adal Rifai [40:34]: "They are all things that are laid."
• Adal Rifai [47:36]: "They are all things that are laid."
• Adal Rifai [59:53]: "It is rollerblades or inline skates."

Key Takeaways

• The episode blends historical trivia with sharp humor, particularly focusing on U.S. Presidents.
• Riddles serve as a core element, with each one leading to creative and humorous improvisational skits.
• Parodied advertisements add a layer of satire, critiquing consumerism while entertaining listeners.
• The hosts maintain a lively and engaging dynamic, making the content accessible and enjoyable for both regular listeners and newcomers.
• Promotions for live tours and Patreon support are seamlessly integrated into the episode's flow.

Note: This summary captures the essence of "Serving Grant!" by highlighting the main discussions, humor, and key segments, making it informative for those who haven't listened to the episode.