Podcast Summary: Good One: A Podcast About Jokes
Episode: Brett Goldstein Loves Making Fun of Shakespeare
Release Date: June 19, 2025

Introduction

In this engaging episode of Good One: A Podcast About Jokes, Vulture Senior Editor Jesse David Fox welcomes comedian and actor Brett Goldstein. The conversation delves into Brett's first stand-up special, his role as Roy Kent in Ted Lasso, his creative process, experiences with award shows, and his broader views on comedy and drama.

Stand-Up Special: The Second Best Night of Your Life

[03:44] Brett Goldstein:
Brett begins by discussing his stand-up special, emphasizing the importance of speaking his truth. He shares his perspective on musicals versus plays, humorously stating, “I love musicals, but I hate plays. Plays are boring and you all know it” ([04:34]). This extreme stance serves as a foundation for his comedic exploration of the subject.

[05:28] Jesse David Fox:
Jesse probes into the origins of this joke, asking Brett about the initial observation that led to this comedic angle.

[05:33] Brett Goldstein:
Brett explains that the joke evolved from combining various bits about plays being boring and his secret appreciation for musicals. He highlights the challenge of dissecting Shakespearean plays, criticizing their complexity and perceived lack of plot coherence.

Crafting Comedy: Observations and Inspirations

[09:50] Jesse David Fox:
Jesse shifts the discussion to Brett's creative influences, particularly the Muppets and Sesame Street. He asks how these influences shape Brett's approach to comedy.

[35:22] Brett Goldstein:
Brett passionately describes The Muppet Christmas Carol as "possibly the greatest film ever made," praising its balance of humor and profound storytelling ([35:50]). He draws parallels between the interactive nature of puppetry and stand-up comedy, emphasizing the symbiotic relationship between performer and audience.

Ted Lasso and the Character of Roy Kent

[14:01] Jesse David Fox:
Jesse delves into Brett's audition process for Ted Lasso, asking him to recount the day he sent his self-tape for the role of Roy Kent.

[14:16] Brett Goldstein:
Brett narrates the experience, highlighting the chemistry with the assistant who read off-camera and the gradual development of Roy Kent's distinctive gravelly voice ([15:15]). He reflects on his initial uncertainties and the subsequent affirmation through positive reception and critical acclaim.

[19:35] Brett Goldstein:
Discussing the Emmy win, Brett shares his disbelief and the pure-hearted experience of receiving the award during the COVID-19 pandemic, contrasting it with his later, more cynical views of the awards industry ([18:00]).

Balancing Comedy and Drama

[34:23] Jesse David Fox:
Jesse addresses the thematic balance between comedy and drama in Brett's work, particularly in Ted Lasso and Shrinking.

[34:35] Brett Goldstein:
Brett asserts, “It has to be funny to be a comedy,” emphasizing that while drama can be as sad as desired, comedy inherently requires humor ([34:35]). He discusses how Shrinking intertwines dramatic narratives with comedic elements to explore complex emotional landscapes.

[33:50] Jesse David Fox:
Jesse probes further into how Shrinking maintains this balance, especially in light of debates surrounding the definition of comedy.

[34:41] Brett Goldstein:
Brett elaborates on the importance of integrating humor into dramatic storytelling to create nuanced and relatable characters ([34:55]).

Experiences with Awards Shows

[17:24] Jesse David Fox:
Jesse inquires about Brett's experiences with award shows, notably winning an Emmy.

[17:27] Brett Goldstein:
Brett reflects on the innocence and magic of the first Emmy win, contrasting it with his later understanding of the industry's complexities and strategic campaigning ([19:35]). He fondly recalls the genuine surprise and joy of seeing his name announced on stage.

Sesame Street and the Magic of Performance

[35:22] Jesse David Fox:
The conversation shifts to Brett's experience filming Sesame Street, which he considers the best day of his life.

[35:04] Brett Goldstein:
Brett recounts his nervousness upon arriving on set and his admiration for the reverence the cast and crew have for Sesame Street. He describes a memorable scene with Cookie Monster, highlighting the show's blend of humor and heartfelt moments ([37:01]).

[40:23] Brett Goldstein:
He draws a parallel between stand-up comedy and puppetry, emphasizing the importance of audience interaction and mutual investment to create magical performances ([40:21]).

Jokes, Bombed Performances, and Comedy Insights

Laughing Round Highlights:

• Favorite Joke:
  [50:19] Brett Goldstein: Shares a self-deprecating joke about a misunderstanding at the airport involving "two pickets for Pittsburgh," only realizing it led to an inappropriate comment ([50:54]).

• Joke from Another Comedian:
  [51:08] Brett Goldstein: Appreciates Adam Sandler's bit from 100% Fresh about unexpected connections on a roller coaster, praising its simplicity and relatability ([51:08]).

• Best Bombed Performance:
  [56:35] Brett Goldstein: Describes a memorable bombing experience in Ibiza where, despite attempts to energize the audience, he faced complete silence. His candid recounting of the failed performance underscores the emotional challenges comedians face ([57:17]).

Advice for Aspiring Actors, Comedians, and Writers

[54:32] Brett Goldstein:
Brett emphasizes the importance of creating original content, urging aspiring artists to "make stuff, make stuff, make stuff" regardless of obstacles. He reflects on his own journey of persistence, highlighting that meaningful success often comes after years of dedication and self-driven projects ([54:32]).

Conclusion

Brett Goldstein's conversation with Jesse David Fox offers a deep dive into the life of a multifaceted comedian and actor. From dissecting Shakespearean narratives to navigating the highs and lows of the entertainment industry, Brett's insights highlight the intricate balance between humor and authenticity in his work. His experiences on Ted Lasso, Sesame Street, and the challenges of stand-up comedy provide a rich tapestry of lessons for both fans and aspiring artists alike.

Notable Quotes:

• “I love musicals, but I hate plays. Plays are boring and you all know it.” – Brett Goldstein ([04:34])
• “Drama without comedy is bad art.” – Brett Goldstein ([33:50])
• “If an audience gives you energy, they will see a better show. It is a two-way street.” – Brett Goldstein ([40:21])
• “Make stuff, make stuff, make stuff. You have no excuse.” – Brett Goldstein ([54:32])

This episode of Good One masterfully captures Brett Goldstein's comedic philosophy, his journey in the entertainment world, and his unwavering dedication to his craft. Whether you're a fan of Ted Lasso or interested in the mechanics of stand-up comedy, Brett's stories and reflections offer both inspiration and entertainment.