Podcast Summary: Hey Riddle Riddle #368: Swan Dong w/ Josh Gondelman

Host/Author: Headgum
Release Date: August 6, 2025

Guests:

• Josh Gondelman: Comedian and guest of the episode

1. Welcome and Introduction (00:01 - 05:31)

The episode opens with the hosts, Aaron Keefe, Adal Rifai, and John Patrick Coan (JPC), engaging in light-hearted banter about a decision Aaron made regarding microdosing psilocybin. They briefly discuss Schedule 35, a Canadian-based startup offering psilocybin products, highlighting its benefits and encouraging listeners to visit their website with a discount code. This segment serves as a sponsored introduction, setting a playful tone for the episode.

Notable Quote:

• Aaron Keefe (00:25): "Schedule 35 is fantastic. It's the smartest decision you've ever made."

2. Substitute Teacher Skit (02:01 - 05:31)

The hosts perform an improvisational skit where JPC adopts the role of a substitute teacher with a real mustache, attempting to manage a class filled with quirky students portrayed by Aaron and Adal. The skit humorously showcases their improvisational skills, emphasizing their ability to create engaging and entertaining scenarios spontaneously.

Notable Quote:

• JPC (02:45): "I am not your regular teacher. I have a real mustache. Find your seat."

3. Welcoming Josh Gondelman (05:31 - 10:17)

Josh Gondelman joins the podcast, and the hosts warmly welcome him back, reminiscing about their previous interactions, including a live show in New York and a recent cruise together. They express genuine admiration for Josh’s comedic talent and discuss his upcoming stand-up special.

Notable Quote:

• Josh Gondelman (05:42): "The last time I recorded with you all was one of my favorite, most fun podcast recording experiences ever."

4. Friendship and Shared Experiences (10:17 - 19:44)

The conversation delves into the hosts' friendship with Josh, highlighting memorable moments such as their first escape room experience in New York. Josh shares how the hosts' expertise in puzzles and riddles enhanced the experience, making it both enjoyable and challenging. They also discuss Josh’s passion for Massachusetts, reflecting on his deep connection to his hometown despite living in New York and frequently traveling.

Notable Quote:

• Josh Gondelman (09:28): "My number one hobby in the world is going somewhere far from Massachusetts and then talking to other people from Massachusetts."

5. Riddles and Trios Segment (19:44 - 43:53)

Adal introduces the "trios" segment, where one host lists three items, and the others must determine their common link. This segment highlights their quick thinking and playful competition.

Example Riddle:

• Adol Refai (14:18): "Travis Barker, Mark Hoppus, and Tom Delonge. What do they have in common?"
• JPC (14:57): "I think they all have an 'X'."

The segment includes various humorous and challenging riddles, fostering an engaging and interactive atmosphere.

Notable Quote:

• JPC (14:57): "They all have an 'X'. X always means 10x's."

6. Sponsored Segments and Advertisements (Skipped)

Per the summary guidelines, advertisements and sponsored segments, including those for Schedule 35, Quince, and Acorns Early, are omitted to focus on the core content of the podcast.

7. Improv Skits and Comedy Scenes (43:53 - 68:31)

The hosts and Josh partake in creative improvisational skits, including scenes where JPC portrays historical figures like Abraham Lincoln in a diner and Greek gods inventing belts. These sketches showcase their comedic timing and ability to weave humor into various scenarios seamlessly.

Notable Quotes:

• JPC (43:40): "I'm president of the good part of America."
• Josh Gondelman (62:59): "They all have sacks. God, you got to imagine Santa Claus would go all pro."

8. Promoting Josh Gondelman's Work (68:31 - 73:21)

Josh takes the opportunity to promote his latest stand-up special, tour dates, newsletter, and his wife's book. The hosts reciprocate by expressing their admiration for Josh’s work and encouraging listeners to check out his projects.

Notable Quote:

• Josh Gondelman (69:16): "Highly, highly recommend positive reinforcement on YouTube. It's at the Bell House, which is one of our favorite venues."

9. Final Skits and Closing (73:21 - 72:17)

The episode concludes with additional improvisational scenes and humorous interactions among the hosts and Josh. They wrap up by thanking listeners and promoting their Patreon for bonus content, maintaining the episode’s entertaining and engaging tone until the end.

Notable Quote:

• JPC (73:21): "This show might mildly ruin your life. I can't recommend it highly enough."

Insights and Highlights:

• Friendship and Collaboration: The deep camaraderie among the hosts and Josh Gondelman is evident, fostering a warm and inviting atmosphere for listeners.

• Improvisational Skills: The seamless integration of skits and improvisational comedy demonstrates the hosts' prowess in creating spontaneous and entertaining content.

• Engaging Content: The "trios" riddles segment adds an interactive layer, engaging both the participants and the audience in solving puzzles and enjoying the playful competition.

• Promotion of Comedy and Creativity: Josh Gondelman's promotion of his work underscores the podcast's role in supporting fellow comedians and creatives.

Conclusion:

Episode #368 of Hey Riddle Riddle successfully blends improvisational comedy, engaging riddles, and heartfelt conversations with Josh Gondelman. The hosts' dynamic interaction and Josh’s contributions create a rich and entertaining listening experience, making it a must-listen for fans of comedy and puzzles alike.

Recommended For: Those who enjoy a mix of humor, improvisation, and light-hearted discussions with a focus on friendship and creative collaboration.

Note: Advertisements and non-content segments have been omitted to maintain focus on the episode's primary discussions and entertaining elements.