Podcast Summary: All Of It with Alison Stewart Featuring Josh Gondelman

Episode Title: Josh Gondelman's New Comedy Special
Release Date: June 25, 2025
Host: Alison Stewart
Guest: Josh Gondelman, Emmy-winning writer and comedian

Introduction

In this episode of All Of It, Alison Stewart welcomes Josh Gondelman, a renowned writer and comedian, to discuss his latest work, Positive Reinforcement. Recorded live at the Bell House in Brooklyn, the conversation delves into the creation of his new comedy special, his experiences in the evolving landscape of comedy, and his perspectives on the future of the creative field.

Josh Gondelman’s New Comedy Special: Positive Reinforcement

Josh Gondelman introduces his new hour-long comedy special, Positive Reinforcement, which is set to stream on YouTube on Friday, June 27th. The special reflects on Gondelman's shift in perspective as he approaches 40, touching on themes such as aging, personal growth, and societal observations.

Key Highlights:

• Opening Joke Strategy: Josh explains his choice to open the special with a seemingly soft joke about his friendliness and texting habits after drinking. He states, “I think it's just a nice way to establish what it's gonna be for the hour” (02:34).

• Recording Venue: The Bell House was chosen for its intimate yet vibrant atmosphere. Josh shares his affinity for the venue, noting, “The Bell House in Union hall and the Comedy Cellar have really started to feel like my comedic homes” (04:04).

• Aesthetic and Production: Collaborating with director Chris Werner and production designer Mark Newell, Josh aimed for a warm and whimsical set design. He describes the backdrop as “like, a touch of playfulness and a little less of, like, you know, a big, gorgeous theater” (05:00).

The Role of Self-Awareness in Comedy

Alison references Jim Gaffigan’s emphasis on self-awareness in comedy and probes Josh on its significance in his work.

Key Insights:

• Essential for Relatability: Josh emphasizes the importance of understanding how the audience perceives him. “I think it's really essential... it helps to know what the impression you're giving off is so you can lean into it or play against it” (06:30).

• Persona Management: Being seen as a friendly individual allows Josh to craft his humor in a gentle manner, contrasting with more abrasive comedic styles. “I can get away with a little more as long as I kind of keep my voice real gentle and smile when I say it” (07:24).

Personal Content and Ethical Comedy

The discussion moves to the balance between personal storytelling and respecting others' privacy in comedy.

Key Points:

• Protection of Individuals: Josh strives to represent people fairly, often changing names or omitting details to avoid “airing people out.” “[I] try to protect the innocent as much as possible” (07:30).

• Incorporating Personal Stories: While his material includes stories about his wife, childhood friends, and even a high school teacher, Josh ensures comedic intent doesn’t harm personal relationships. He humorously apologizes for “throwing [his] high school history teacher under the bus for comedic effect” (08:08).

Influence of YouTube and Digital Platforms on Comedy

Alison and Josh explore how platforms like YouTube have transformed the comedy landscape.

Key Observations:

• Increased Accessibility: YouTube allows comedians to share work-in-progress material, fostering rapid idea sharing and showcasing dynamic performances. Josh remarks, “It opens people up to new voices that might not have had an outlet for like an hour-long special in the past” (10:07).

• Challenges with Oversaturation: The abundance of content makes it difficult for individual comedians to stand out amidst the “flood of stuff” (10:07).

Navigating Generational Shifts in Comedy

Josh reflects on feeling part of an older generation within the comedy scene, especially post-COVID.

Insights:

• Generational Divide: Approaching 40, Josh feels a noticeable gap between himself and younger comedians, leading to a sense of being from “a different time” (11:35).

• Responsibility and Expectations: With age comes the expectation of expertise and reliability in his craft. “I kind of am expected to be good and know what I'm doing” (12:17).

Concerns About Artificial Intelligence in the Creative Field

Alison probes into Josh’s thoughts on the rise of AI and its impact on creative industries.

Key Points:

• Skepticism and Disdain: Josh expresses strong reservations about AI’s role in creativity, labeling himself “an incurable hater” of AI advancements that he feels are prematurely integrated without readiness (13:48).

• Misinformation Issues: He shares a personal anecdote where AI incorrectly linked him with Fiona Apple, highlighting inaccuracies and the potential harm of AI-generated content (14:24).

Crafting and Refining Comedy Material

The conversation touches on the creative process behind developing stand-up material.

Key Strategies:

• Trial and Error: Josh acknowledges the importance of testing material live and being willing to adapt or discard jokes that don’t resonate. “If it doesn't connect... I might as well tickle people individually” (16:12).

• Versatility in Formats: He considers reformatting jokes that don’t work on stage for other mediums like personal essays for publications such as The New Yorker or McSweeney's (16:12).

Audience Interaction and Show Rhythm

Alison inquires about how audience reactions influence Josh’s performance.

Key Insights:

• Balancing Authenticity and Adaptation: Josh strives to maintain his natural comedic expression while reading the room and sometimes adjusting to better connect with the audience. “[...] making art is about doing it as close to the way you feel like is your natural expression” (17:17).

• Avoiding Forced Content: He resists altering his material solely for laughs, aiming instead for genuine engagement. “My goal isn't to come in doing just, like, the thing that will make audience members laugh if I don't like” (17:17).

Promotion of Josh Gondelman’s Comedy Album

Josh discusses his new comedy album produced alongside his special.

Details:

• Extended Content: The album includes additional bits not featured in the special, offering a richer listening experience. “There's a bunch of different stuff as well. A bunch of stuff added” (18:24).

• Nostalgia for Comedy Albums: He shares his love for the medium, reminiscing about listening to comedy records as a child and preferring audio experiences for their intimacy. “I would sometimes prefer to, like, listen and really, like, lock into it that way” (18:24).

Goals for Audience Experience

Concluding the discussion, Josh outlines his aspirations for how audiences will feel after engaging with his work.

Key Objectives:

• Elicit Genuine Laughter: His primary aim is for listeners to “feel like they laughed” with a lasting sense of joy (19:44).

• Create an Inclusive Atmosphere: Josh wants his performances to be welcoming, ensuring that audiences feel included rather than alienated. “I wanted everybody to kind of feel like they had just a warm, fun experience” (19:44).

Upcoming Segments

Following the interview with Josh, Alison Stewart introduces the next guest, writer and comedian Maris Kreitzman, who will discuss her new book I Want to Burn this Place Down. The episode concludes with a brief promotional segment for Progressive Insurance and NYC Now.

Notable Quotes

• “I am very friendly offstage, but I'm also very friendly on stage.” – Josh Gondelman (02:34)

• “It opens people up to new voices that might not have had an outlet for like an hour long special in the past.” – Josh Gondelman (10:07)

• “I'm an incurable hater about that stuff.” – Josh Gondelman on AI (13:48)

• “I want people to feel like they laughed I want that good soreness from laughing.” – Josh Gondelman (19:44)

Conclusion

This episode of All Of It offers an insightful look into Josh Gondelman’s creative process, the nuances of modern comedy, and his personal reflections on navigating an ever-changing cultural landscape. Listeners gain a deeper understanding of what it takes to produce a meaningful and engaging comedy special in today’s digital age.