Hey Riddle Riddle Podcast Episode #355: "Caterpillar Blood" Featuring Matt Oberg

Release Date: May 7, 2025
Guest: Matt Oberg

Episode Overview

In episode #355 of Hey Riddle Riddle, the Headgum hosts—Adol Rifai, Erin Keif, and John Patrick Coan (JPC)—welcome special guest Matt Oberg. Known for his versatile roles, including voicing Kite Man, Matt brings a blend of humor and intellect to the show. The episode seamlessly intertwines challenging riddles, engaging improvisational scenes, and lively banter, all centered around the theme of "Caterpillar Blood."

Guest Introduction: Matt Oberg

The episode kicks off with the hosts introducing Matt Oberg, expressing enthusiasm for his participation. Matt humorously anticipates potential challenges, stating, “[00:46] Matt Oberg: Well, Aaron might have a breakdown,” to which JPC quips back, “[00:48] Aaron Kenck: Yeah, I could have a breakdown. I hate. I hate riddles.” This sets a playful tone for the episode.

Notable Quote:

• JPC: “[02:29] Matt Oberg: Oh, wait a minute. I might know someone who is a doctor or might have played a doctor before... Please welcome Matt Oberg.”

Riddle Discussions

Aaron Kenck spearheads the riddle segment, presenting Matt with a collection of lateral thinking puzzles from a book titled Lateral Thinking Puzzles. Although Matt expresses skepticism about riddles, the collaborative effort to solve them keeps the conversation lively.

First Riddle Example:

• Riddle: “I'm always at home, but I never pay rent. Waiting for me would be time long spent.”
• Discussion: The hosts initially contemplate abstract answers like a hermit crab, but the solution gravitates towards something more tangible like a "key."

Notable Quote:

• Aaron Kenck: “[13:08] Aaron Kenck: ...I have many jagged teeth and usually stay with a pack. I make my home in a cave, filling up every crack.”

Improvisational Scenes

The episode features several spontaneous improvisational scenes that highlight the comedic talents of both the hosts and Matt Oberg.

1. Doctor Dad Scene

At [09:02], Matt portrays "Dr. Dad," blending the roles of a father and a physician to convince a reluctant child to attend school. The scene humorously juxtaposes medical seriousness with parental nagging.

Notable Quote:

• JPC: “[10:25] JPC: ...there's no excuse for not showing up.”

2. Turtle Housewarming Party

Later, at [15:12], the group imagines JPC as a turtle hosting a housewarming party. Matt arrives as a guest, bringing blenders as unconventional gifts, leading to a series of comedic exchanges about pet turtles and quirky home setups.

Notable Quote:

• Matt Oberg: “[15:24] Matt Oberg: Hi, my dudes.”

3. Dog Boxing Match Scene

In a particularly entertaining segment starting at [58:03], Matt's character "Oreo" faces off against the legendary boxer Evander Holyfield in the ring. Adol Refai acts as the over-the-top announcer, creating a humorous narrative around the unlikely match.

Notable Quote:

• Matt Oberg: “[59:57] Matt Oberg: Evander Holyfield versus Oreo and event.”

Notable Riddles and Team’s Attempts

Throughout the episode, Aaron presents a series of riddles, challenging the team's problem-solving skills amidst humorous distractions.

Example Riddle:

• Riddle: “What took 19 years to get into itself?”
• Discussion: The team explores various angles, including historical events and popular culture references, but struggles to arrive at the correct answer, highlighting the complexity of lateral thinking puzzles.

Second Riddle Example:

• Riddle: “A boxer left the ring after winning the world championship. His trainer took all the money, and he never got a cent. Why not?”
• Solution: The answer plays on the homophone “scent,” revealing that the boxer never got a “scent” instead of a “cent.”

Notable Quote:

• Aaron Kenck: “[58:15] Aaron Kenck: A boxer left the ring... Why not?”
• Adol Refai: “[58:20] Adol Refai: He never got a scent.”

Insights and Humor

The episode is rich with humorous interactions and insightful observations. The hosts discuss everyday objects like key rings and rings, blending practical advice with comedic exaggerations. For instance, when Aaron showcases his overloaded key ring, the conversation shifts to the symbolism of rings and their personal significance.

Notable Quote:

• Aaron Kenck: “[28:29] Aaron Kenck: You just keep your keys with other.”

Additionally, the segment involving the flipped ring by Adol's niece adds a layer of familial humor and relatability.

Matt Oberg’s New Podcast Plug: "Extraordinarians"

Midway through the episode, Matt Oberg introduces his new podcast, Extraordinarians, which delves into conversations with individuals who have broken unique world records. He highlights the inspiring and profound nature of these interactions, emphasizing themes of ambition, confidence, and risk-taking.

Notable Quote:

• Matt Oberg: “[70:32] Matt Oberg: That's awesome.”

JPC adds:

• “[71:21] JPC: ...we have, you know, 20-minute conversations with...”

The hosts express genuine enthusiasm for Matt’s project, recognizing the podcast’s potential to inspire listeners.

Conclusion

As the episode wraps up, the hosts and Matt engage in light-hearted banter, reflecting on the challenges of solving riddles and the fun of improvisational acting. They also share plugs for each other's projects and sponsor segments, maintaining the episode's entertaining and collaborative spirit.

Notable Quote:

• Adol Refai: “[73:39] JPC: Scooter McGreevy. Come a court.”
• Aaron Kenck: “[73:11] Matt Oberg: Vincent D'Onofrio. If you've never seen The Cell...”

The episode concludes with a playful mishap involving a cat, leaving listeners with a final laugh and anticipation for future episodes.

Final Quote:

• Aaron Kenck: “[74:07] Matt Oberg: This is a Headgum podcast.”

Key Takeaways

• Engaging Riddles: The episode balances the complexity of riddles with the hosts' lighthearted attempts to solve them, showcasing the appeal of lateral thinking puzzles.

• Dynamic Improvisation: Matt Oberg's contributions to improvisational scenes add depth and humor, highlighting his versatility as an actor.

• Collaborative Spirit: The camaraderie among the hosts and their guest fosters an entertaining and inclusive listening experience.

• Promoting Creativity: Discussions about new projects like Extraordinarians emphasize the hosts' commitment to creative endeavors in the podcasting space.

Overall, episode #355 of Hey Riddle Riddle delivers a captivating mix of puzzles, humor, and insightful conversations, making it a must-listen for fans and newcomers alike.