Fail Again: Ben Stiller Confronts His Parents' Legacy

Fail Better with David Duchovny — Lemonada Media
Release Date: October 21, 2025

Episode Overview

The debut episode of Fail Better, hosted by David Duchovny, opens with a conversation between Duchovny and Ben Stiller about the universal experience of failure and how it shapes personal and creative growth. This candid exploration revolves around confronting professional and personal setbacks, the weight of legacy—especially as children of performers—and the evolution that comes with facing (and embracing) failure. The episode as revisited here ties in with the release of Ben Stiller’s documentary about his famous parents, Stiller and Meara: Nothing Is Lost.

Key Discussion Points & Insights

1. The Podcast’s Genesis and Duchovny’s Relationship to Failure

• Duchovny introduces the show with vulnerability, recalling his own experiences with shame and public criticism, notably the harsh review of his film House of D.
  • Quote: "I realized in that moment that I felt so light and free is because my whole life, I'd been terrified of getting an F... And here I was...and I'd had my F. Because I realized that you don't die when you get an F." — David Duchovny (05:05)
• The core theme: Failing is inevitable, and reflecting on our responses to failure can free us from shame.

2. Early Failures: Building Careers in Comedy and Acting

[07:33]

• Ben Stiller and Duchovny reminisce about their first collaboration on Zoolander. Duchovny recalls feeling liberated by making a mistake on set and being accepted by Stiller and the crew.
  • Quote: "I was so liberated by that because there I was trying to be perfect...that was like a moment of gratitude I had for you as a director, as a creative artist and everything.” — Duchovny (09:09)
• Stiller shares stories about on-set nerves, early auditions, and the formative power of small roles and failures.

3. Reflections on Youth, Confidence, and Change

• Both discuss how early-career overconfidence transitions, with age, into humility and self-awareness.
  • Quote: "There's an eagerness that is kind of winning, you know?...And then at some point I feel like I lost that eagerness." — Duchovny (16:14)
• Stiller notes that youthful lack of self-awareness sometimes led him into situations without knowing why, guided only by love for the industry.

4. Defining Career Failures: The Cable Guy & Zoolander 2

[17:27]

• Stiller details two landmark moments of professional disappointment: the critical and commercial receptions of The Cable Guy and Zoolander 2. Both resulted in self-doubt and career lulls.
  • Quote: "When the movie came out, it was not well received...I remember where I was...and like opening up the New York Times review which said the first disaster movie of the summer has arrived. And it's called the Cable Guy." — Ben Stiller (17:52)
  • "On Zoolander 2...I must have really fucked this up. That, like, everybody didn't go to it and it's gotten, like, these horrible reviews. It really freaked me out..." — Stiller (22:10)
• They discuss how the silence that follows a perceived failure is often worse than harsh critique.

5. Transformation Through Failure

• Stiller shares how professional setbacks forced him into periods of introspection and allowed him to experiment with new creative directions (e.g., directing Escape at Dannemora).
  • Quote: "If that had been a hit and they said, like, make Zoolander 3 right now...I would have just probably jumped in and done that. But I had this space to just kind of sit with myself and have to deal with it.” — Stiller (24:07)

6. Family Legacies and Expectations

[29:50]

• Duchovny and Stiller both describe growing up with parents in show business, noting the unique pressures and implicit expectations of legacy.
• Stiller discusses seeking attention and validation from his famous parents, Jerry Stiller and Anne Meara:
  • Quote: "Maybe it's little Ben Stiller wanted to get, you know, Jerry and Anne to laugh at him and to pay attention." — Stiller (30:36)
• Family life blurred with performance; as children, Stiller and his sister would imitate their parents’ act.
  • Quote: "There was a lot of performing going on in the house...We would just, like, act out, like, the first act of Jesus Christ Superstar..." — Stiller (33:14)

7. Navigating Parental Anxiety and Generational Cycles

• Stiller describes his parents as always hustling, never experiencing full security in their careers; Duchovny notes how as children, the presence on TV looked like total success.
• Duchovny introspects on re-parenting one's self when raising kids, oscillating between encouraging persistence and accepting loss.
  • Quote: "It's funny how we kind of...reparent ourselves when we parent our kids, you know, and we make different mistakes than our parents made." — Duchovny (39:18)
• Stiller relates his own struggle with being absent from his children's lives because of work—mirroring his experience growing up.

8. Self-Actualization, EST, and Childhood Experiences

[47:24]

• Duchovny uncovers Stiller’s participation in the self-improvement programs EST and Silva Mind Control as a child—both hallmarks of 1970s self-actualization culture:
  • Quote: "Nobody has ever asked me about silver mind control. I did it when I was literally...15 or 16." — Stiller (47:56)
• Stiller explains Silva’s techniques and the EST training, focusing on practicing visualization and radical personal responsibility.
  • Duchovny ties this to Stiller’s comedic persona—how angry, truth-telling outbursts often mark a turning point in his films.

9. The Comedy of Anger: A Family Connection

• Duchovny observes a pattern: Ben’s skill at making anger funny echoes Jerry Stiller’s comedic rage, especially as Frank Costanza and Arthur Spooner.
  • Quote: "There's always a moment in the funny Ben Stiller film where you fucking tell the truth...and then you go est on everybody." — Duchovny (51:04)
  • "My dad, who I think was, like, truly just one of the funniest people ever...The way that he blow up and get angry...I always felt, was...him releasing so much real rage and anger." — Stiller (52:25)

10. The Loop of Failure and Growth

[55:08]

• Meta-moment: Duchovny, in a self-reflective post-interview segment, expresses lingering self-doubt about his new role as interviewer.
  • Quote: "I feel like a failure...you have this idea of what things are going to be. Who knows, you know, maybe I'll figure it out for next time a little more...But what we don't get is what's the process? How long does it take? What is the mental process? What is the spiritual process?" — Duchovny (55:19)
• Both Duchovny and Stiller agree that talking honestly about these topics is itself healing and productive.

Notable Quotes & Memorable Moments

• "You don't die when you get an F." — Duchovny (05:25)
• "There's an eagerness that is kind of winning, you know? And then at some point I feel like I lost that eagerness. And then like, what do you replace that with? ... You become a different kind of a maker." — Duchovny (16:14)
• "I must have really fucked this up...It really freaked me out because I was like, yeah, I didn't know it was that bad. That's what scared me the most on that one..." — Stiller on Zoolander 2 (22:10)
• "If that had been a hit...I would have just probably jumped in and done that. But I had this space to just kind of sit with myself and have to deal with it. ... It ended up giving me the space. ... I was so happy doing it. That kind of set me off on a different path." — Stiller (24:07)
• "Maybe it's little Ben Stiller wanted to get, you know, Jerry and Anne to laugh at him and to pay attention." — Stiller (30:36)
• "You make different mistakes than your parents made." — Duchovny (39:18)
• "There's always a moment in the funny Ben Stiller film where you fucking tell the truth...and then you go est on everybody..." — Duchovny (51:04)
• "My dad...The way that he blow up and get angry, I always felt, was that was him releasing so much real rage and anger...he found this way to channel it in a way that was so incredibly funny but it was coming from such a real place." — Stiller (52:25)
• "I just didn't want to fail." — Stiller, on playing drums at Duchovny’s band rehearsal (54:58)

Timestamps for Key Segments

• Introduction & Duchovny’s "F" Story: 00:53 – 07:33
• Collaboration on Zoolander & Early Creative Fears: 07:33 – 16:53
• Career Failures (Cable Guy, Zoolander 2): 16:53 – 24:07
• Parent’s Legacy, Childhood, & Family Performance: 29:50 – 39:18
• Parenting and Intergenerational Patterns: 39:18 – 43:44
• EST, Silva Mind Control & Comedy of Anger: 47:24 – 53:27
• Meta-Reflection on Interviewing & Failure: 55:08 – 55:59

Takeaways

• Failure is an unavoidable, identity-shaping force.
  Both guests openly discuss high-profile failures and the transformative voids they create, ultimately becoming new ground for growth and self-discovery.
• The shadows and gifts of family legacy run deep.
  The conversation delves into inherited anxieties, creative impulses, and the ways we repeat or react against our parents’ lives and choices.
• Talking about failure is both an act of vulnerability and community.
  Stiller and Duchovny’s willingness to articulate self-doubt makes space for shared humanity and connection.

Tone and Style

Wry, self-effacing, deeply honest and warm, full of banter and the gentle ribbing of old friends, this episode balances humor with truly moving moments. Stiller, in particular, is candid about the pain and hidden blessings of failure, while Duchovny threads personal anecdotes and philosophical musings throughout.