Introducing Stephen Colbert on connection, discovery and human nature from Possible.
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What could we gain—and what might we lose—when technology begins to approximate the contours of human connection and presence? In this episode, Reid and Aria chat with comedian, actor, and political commentator Stephen Colbert. Best known for hosting The Colbert Report and The Late Show, Stephen combines a razor sharp satire with a sincere curiosity about the world. Together, Reid, Aria, and Stephen discuss the art of live performance, the many lessons one can learn from J.R.R. Tolkien, and the nature of creativity, humor, and imagination in the age of AI. The result is a meditation on discovery, empathy, and the bonds that make connection more than performance — but a shared act of being human.
For more info on the podcast and transcripts of all the episodes, visit https://www.possible.fm/podcast/
Topics:
2:35 – Hellos and intros
2:53 – Stephen Riffs on humanity and Dungeons & Dragons
6:08 – Tolkien characters and desert island companions
7:02 – Creativity, empathy, and imagination in comedy
11:37 – Performing for a live audience
13:02 – Comedy as a third space
16:22 – Early ideas about interactive technology and improvisation
19:14 – Can AI art escape the uncanny valley
22:27 – The human “micronutrients” that AI cannot replace
24:05 – Parasocial relationships and the future of entertainment
26:50:– Midroll
26:58 – Responsibility and fact-checking
29:56 – Personalization versus discovery in AI storytelling
33:47 – Lessons from Tolkien
41:22 – AI as part of human evolution
44:51 – How AI can already be employed in health fields
48:46 – AI in video games and creative amplification
49:58 – Balancing skepticism and excitement about AI
50:06 – Rapid-fire Questions
Select mentions:
A Man Jumps Out of an Airplane by Barry Yourgrau
Exploring The Lord of the Rings with Dr. Corey Olsen
Letter 144 by J.R.R. Tolkien
Robert Heinlein
Possible is an award-winning podcast that sketches out the brightest version of the future—and what it will take to get there. Most of all, it asks: what if, in the future, everything breaks humanity's way? Tune in for grounded and speculative takes on how technology—and, in particular, AI—is inspiring change and transforming the future. Hosted by Reid Hoffman and Aria Finger, each episode features an interview with an ambitious builder or deep thinker on a topic, from art to geopolitics and from healthcare to education. These conversations also showcase another kind of guest: AI. Each episode seeks to enhance and advance our discussion about what humanity could possibly get right if we leverage technology—and our collective effort—effectively.
DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to team@podroll.fm.
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- FrequencyUpdated weekly
- Published12 September 2025 at 09:50 UTC
- RatingClean