Episode Summary: Ben Stiller Explains Severance’s Early Days, Mysteries & "Weird" Tone, Talks Happy Gilmore 2

Podcast: Good One: A Podcast About Jokes
Host: Jesse David Fox
Guest: Ben Stiller
Release Date: August 7, 2025

Introduction

In this engaging episode of "Good One: A Podcast About Jokes," hosted by Jesse David Fox, comedy icon Ben Stiller joins to discuss his multifaceted career. Stiller delves into his role as the director of the acclaimed series "Severance," his return to the comedic universe with "Happy Gilmore 2," and reflects on his extensive body of work, including beloved films like "Zoolander," "The Cable Guy," and "Tropic Thunder." The conversation offers a deep dive into the creative processes, challenges, and personal insights that have shaped Stiller's journey in comedy and beyond.

Exploring "Severance" and Its Unique Tone

Balancing Comedy with Mystery

Ben Stiller provides an in-depth look into the creation of "Severance," highlighting how writer Dan Erickson masterfully blends workplace comedy with underlying sci-fi mysteries.

Ben Stiller [06:21]: "I have to really just give credit to Dan Erickson because he wrote it in the script. And it was that blend of this sort of, you know, comedic tone within the workplace…"

Stiller discusses the challenges of maintaining this delicate balance, ensuring that the humor complements the mysterious elements without overwhelming them.

Visualizing the MDR Room

Stiller explains the conceptualization of the show's setting, particularly the MDR room, and the collaborative efforts with designers to bring Erickson's vision to life.

Ben Stiller [07:42]: "When he described the MDR room… the idea of all these hallways and the idea of this place where you could kind of get lost in it…"

He emphasizes the importance of creating a believable yet eerie environment that supports the series' tone.

Tone Modulation in Specific Scenes

Discussing specific scenes, Stiller sheds light on how tone is carefully modulated during the editing process to maintain consistency and enhance viewer engagement.

Ben Stiller [17:34]: "Jeff Richman, who's our editor, has a real great sense for that. And, yeah, that's sort of finding it as you go along…"

Stiller highlights the iterative nature of editing, where scenes are fine-tuned to achieve the desired emotional and comedic impact.

Reflections on Collaborative Relationships

Long-standing Friendship with Adam Sandler

Stiller reminisces about his enduring friendship and professional collaborations with Adam Sandler, noting how their paths have intertwined over the years.

Ben Stiller [03:37]: "We've had fun over the years as friends and worked together in other projects…"

He discusses the evolution of their relationship and how it influences their creative endeavors.

Working with Patricia Arquette and John Turturro

Stiller shares insights into his collaborative dynamics with Patricia Arquette and John Turturro, emphasizing mutual trust and creative experimentation.

Ben Stiller [10:05]: "Patricia is this brilliant actor who I feel very comfortable with…"

He describes how these relationships enhance the authenticity and depth of the performances in "Severance."

Insights from Past Projects

Directing "Tropic Thunder"

Stiller reflects on his experience directing "Tropic Thunder," focusing on Robert Downey Jr.'s commitment to his role and the film's satirical approach to Hollywood.

Ben Stiller [39:34]: "Robert Downey, as an actor, believes that this is what he's going to do to play this character…"

He discusses the cultural context of the film and its relevance today.

Creating "The Cable Guy"

Ben recounts the creation of "The Cable Guy," highlighting a memorable dance scene that parallels his work on "Severance."

Ben Stiller [32:13]: "When we made that, it was just sort of trying to capture his sort of energy…"

He draws connections between his past and current projects, illustrating his evolving comedic style.

Developing "Zoolander"

Stiller talks about "Zoolander," focusing on the satirical portrayal of the modeling industry and the fine line between humor and critique.

Ben Stiller [47:45]: "Models have a sense of humor about themselves…"

He explains how maintaining character likability is crucial to the film's success.

Upcoming Projects: "Happy Gilmore 2" and "Meet the Parents 2"

Returning to the Adam Sandler Universe

Ben expresses excitement about reprising his role in "Happy Gilmore 2," discussing the challenges and joys of returning to a beloved character.

Ben Stiller [02:19]: "It was pretty crazy because it was, you know, being back to doing that character…"

Sequels in the "Meet the Parents" Series

Stiller teases his involvement in the sequel to "Meet the Parents," starring Ariana Grande, highlighting the natural progression and personal relevance of the project.

Ben Stiller [45:58]: "It felt like this situation of my son and where he's at and meeting a woman… could take us back to the first movie…"

Personal Reflections: Balancing Work and Life

Integration of Creative and Personal Life

Stiller opens up about balancing his demanding career with his personal life, sharing his experiences as a parent and the influence of his own parents on his career trajectory.

Ben Stiller [56:47]: "I feel like what I am, what I know and also from making this movie… it's more integrated to me now than it has…"

Influence of Musicals and Early Creative Exposure

He reflects on how early exposure to musicals and theater shaped his creative sensibilities and inspired his career path.

Ben Stiller [51:46]: "I remember seeing Sweeney Todd too, when I was a kid and really being affected by that…"

Behind-the-Scenes Anecdotes

First Day Shooting with Robert De Niro

Stiller shares a memorable experience from the first day of shooting "Meet the Parents" with Robert De Niro, highlighting both the excitement and the challenges of working with a legendary actor.

Ben Stiller [67:08]: "Doing the first scene with him and just thinking, this is crazy…"

Memories from "Saturday Night Live"

He reminisces about his brief stint on "Saturday Night Live," recalling the intense work schedule and the camaraderie with fellow comedians.

Ben Stiller [66:05]: "Writing sketches, trying to get on… it was so exhausting…"

Attending a Knicks Game with Timothee Chalamet

Ben recounts a humorous incident from attending a Knicks game with Timothee Chalamet, expressing regret over his courtside seats due to unexpected chaos.

Ben Stiller [65:08]: "I could see Miles Turner… and they almost fell on top of us. And it was just awful. It was the worst."

Encounter with Jerry Lewis

Stiller narrates his backstage encounter with Jerry Lewis during a performance of "Damn Yankees," emphasizing the influence Lewis had on him and his parents.

Ben Stiller [63:35]: "He was very nice… I love your parents. And then I said, oh, I have my friends with me…"

Personal Growth and Creative Integration

Navigating Career Transitions

Reflecting on a pivotal moment in 2017, Ben discusses how less successful projects led him to focus on authentic creative endeavors, ultimately contributing to the development of "Severance."

Ben Stiller [55:44]: "I got to this point… let me just do what I want to be doing…"

Documentary on Parents: Mira and Jerry Stiller

Stiller talks about his documentary exploring his parents' careers and their impact on his life, highlighting the intertwined nature of personal and professional influences.

Ben Stiller [52:42]: "It's like, as a person, if this is what you know, creatively, how you want to express yourself…"

Humorous Interludes and Final Thoughts

Favorite Jokes and Funny Moments

In the final segment, Stiller shares a favorite joke and amusing anecdotes from his career, including his brief time on "Saturday Night Live" and memorable on-set moments.

Ben Stiller [63:05]: "I don't have a favorite joke. The one I told my kids yesterday was…"

A Lighthearted Goodbye

The episode concludes with light-hearted farewells and final thoughts, leaving listeners with a sense of Ben Stiller's humor and depth.

Ben Stiller [68:22]: "All right, that's it. All right, man. Great talking to you. Thank you. Appreciate it."

Conclusion

This episode offers a comprehensive exploration of Ben Stiller's creative genius, his ability to blend humor with complex narratives, and his reflections on personal growth and professional relationships. Through candid conversations and insightful anecdotes, listeners gain a deeper understanding of what makes Ben Stiller a standout figure in both comedy and dramatic storytelling.