Podcast Title: Senses Working Overtime with David Cross

Episode: Michael R. Jackson

Release Date: June 26, 2025

Introduction and Guest Background (00:00 - 05:00)

The episode kicks off with a light-hearted introduction where host David Cross welcomes Michael R. Jackson to the show. David humorously points out Michael's resemblance to Jake (a mutual acquaintance) and delves into Michael's connection with Lin-Manuel Miranda, highlighting their proximity in Washington Heights. Michael shares anecdotes about his friendship with Miranda, emphasizing his admiration for Miranda's kindness and talent.

David Cross: "If anybody ever looked like a Jake, it's this gentleman. You look so Jakeish to me. Thank you for coming."

Evolution of Comedy and Digital Impact (05:00 - 15:00)

The conversation shifts to the changing landscape of comedy, particularly the influence of digital platforms and artificial intelligence (AI). Both David and Michael express their frustrations with how modern stand-up comedians leverage algorithms and digital content creation, feeling it dilutes the purity and hard-earned craft of traditional stand-up.

Michael R. Jackson: "There's human AI and there's like digital AI and the digital AI is just mimicking us. Mimicking it. Mimicking us, Mickey."

They discuss the generational gap in comedy appreciation, with older comedians feeling alienated by the shortcuts digital platforms afford newer comedians. Michael touches on the rapid rise of multimillionaires on YouTube and streaming services, contrasting it with the traditional grind of touring and paying dues.

David Cross: "A lot of stand ups certainly have that same view. A lot of older standards."

Theater Insights and "A Strange Loop" (15:00 - 30:00)

Michael provides an in-depth look into his acclaimed work, "A Strange Loop," detailing its journey from conception to Broadway success. He shares the decade-long dedication required to develop the musical, starting from a monologue in grad school to its eventual Pulitzer and Tony awards. The discussion highlights the complexities of marketing in the modern era, where critical acclaim no longer guarantees box office success.

Michael R. Jackson: "It was longer than that. So I started working on a monologue called 'Why I Can't Get Work' right after I graduated from college. And that became the seed of the piece."

David reflects on the challenges of maintaining artistic integrity amid changing industry dynamics, acknowledging how award-winning shows now rely more on word-of-mouth than traditional marketing.

Influence of International Productions (30:00 - 40:00)

Michael recounts his experiences with international productions of "A Strange Loop," particularly the Canadian premiere. He contrasts the American and Canadian approaches to the show's humor and cultural references, noting that Canadian actors embraced stereotypes more freely, enhancing the comedic impact.

Michael R. Jackson: "They just sort of leaned into it even more, which I think was helpful because the audience in general, there is a different mindset about what was happening."

David and Michael discuss the variations in reception across different cultures, pondering how globalization affects the interpretation and appreciation of theater.

Favorite Shows and Personal Recommendations (40:00 - 55:00)

The duo shares their favorite theatrical productions, with Michael praising "Oh Mary" for its blend of old and new comedic elements. They delve into the nuances of what makes a show resonate, emphasizing the importance of intelligent humor and strong performances.

Michael R. Jackson: "Oh Mary, oh Mary, oh Mary, number one. Like, I've seen it six, seven times."

They also touch upon other favorite shows like "Happy Endings," discussing how contemporary themes and sophisticated humor contribute to their appeal. The conversation includes humorous interludes about sitcoms and soap operas, offering a nostalgic take on classic television.

Behind the Scenes: Marketing and Awards (55:00 - 65:00)

Michael discusses the unpredictable nature of theater marketing, critiquing how marketing departments can both elevate and undermine productions. He shares his experiences with award nominations, including losing the Grammy to Stephen Sondheim and the Olivier Award to Frank Lesser, emphasizing the competitive and often subjective nature of accolades in the arts.

Michael R. Jackson: "I lost the Grammy Award to Stephen Sondheim."

David reflects on the evolving significance of awards, noting that critical recognition no longer guarantees commercial success as it once did.

Personal Anecdotes and Final Thoughts (65:00 - End)

The conversation concludes with personal anecdotes, including Michael's time interning at "All My Children" and his experiences reading fan mail from prisoners. They discuss the impact of soap operas on their lives and the broader cultural landscape, blending humor with insightful reflections on media consumption.

Michael shares his current projects, including an opera titled "Complications in Sue," set to premiere in Philadelphia. He discusses the collaborative nature of opera production and his ongoing creative endeavors, showcasing his dedication to the craft.

Michael R. Jackson: "I am sort of, after three, like, many years of like, back to back shows, I'm sort of like back in my little laboratory."

In a light-hearted finale, David poses a whimsical question from his daughter about the varying number of days in each month, to which Michael responds with playful simplicity.

Michael R. Jackson: "Because I said so."

David wraps up the episode with gratitude, highlighting the collaborative efforts behind the podcast.

Notable Quotes

• David Cross (02:50): "I have a T shirt that says board B O R E D of the soho rep."
• Michael R. Jackson (10:35): "I understand people have always gotten in through backwards doors and unfairness and nepotism and all those things."
• David Cross (58:59): "Tony Award winning, Pulitzer Prize winning, prize winning, Michael R. Jackson Grammy Award losing."

Key Takeaways

1. Challenges in Modern Comedy: The shift towards digital platforms and AI in comedy creation is causing generational rifts, with established comedians feeling supplanted by digitally savvy newcomers.

2. Theatrical Journey of "A Strange Loop": Michael R. Jackson's dedication to "A Strange Loop" exemplifies the perseverance required in the arts, navigating from initial conception to critical acclaim amid changing industry standards.

3. Cultural Adaptation in International Productions: Productions like "A Strange Loop" adapt differently in international settings, with Canadian actors embracing broader stereotypes to enhance comedic effect.

4. Impact of Marketing and Awards: The evolving nature of theater marketing and the diminishing commercial impact of awards present new challenges and dynamics for modern productions.

5. Personal Experiences in Media: Michael's background in soap operas and his unique interactions with fan mail provide a behind-the-scenes look at the intersection of media and personal life.

Conclusion

This episode of Senses Working Overtime with David Cross offers a rich exploration of the evolving landscapes of comedy and theater through the lens of Michael R. Jackson. From the gritty realities of modern stand-up to the intricate journey of an award-winning musical, listeners gain invaluable insights into the dedication and adaptability required in the performing arts. Notable for its humorous exchanges and profound discussions, the episode serves as an engaging guide for both enthusiasts and newcomers alike.