Fail Better with David Duchovny

Episode: “Fail Again: Sean Penn and the Squared-Away Individual”
Date: January 27, 2026
Host: David Duchovny
Guest: Sean Penn

Episode Overview

This intimate, in-person conversation between host David Duchovny and acclaimed actor/director Sean Penn centers on the deeply human themes of failure, self-definition, and the artistry of transformation. Duchovny and Penn discuss not just the mechanics of acting, but the emotional plumbing that connects failure with growth, risk, and self-acceptance. Touching on Penn’s early life, the evolution of his craft, directing, and his navigation of fame and misinterpretation, the episode is rich with insights, industry anecdotes, and reflections on living authentically in an age of exposure.

Key Discussion Points & Insights

1. The Shifting Nature of Celebrity & Privacy in Acting

• Duchovny opens with reflections on how previous eras kept actors more anonymous, which allowed audiences to more freely believe in their transformations on screen.
  • “The less you know about me, the more freedom I have to become someone else.” (David Duchovny, [01:14])
  • Both Duchovny and Penn express some nostalgia for, and continued commitment to, privacy as a professional value.
• Fear vs. Magic: Duchovny relates his own hesitation about podcasting—worries that too much openness could dilute his “magic trick” as an actor. ([02:16])

2. Roots: Early Life, Motivation, and Internal Sense of Success/Failure

• Penn describes growing up between San Fernando Valley and Malibu, and an early drive to “square away” disorder as a source of accomplishment.
  • “I could be... on my hands and knees for 10 hours, getting every stray pebble out of there and getting that dirt swept under those trees. ...They always gave me a great feeling of accomplishment when things were squared away.” (Sean Penn, [05:50])
• Career Aspirations: Wanted to be a defense attorney like F. Lee Bailey, but realized his schoolwork hadn’t set him up for law.
• Stumbling into Acting: Started making Super 8 films due to his brother’s experiments, eventually stepping in as actor by necessity.
  • The acting “clicks” after hearing Anthony Zerby speak at a career day ([09:50]), and inspired by his “actor shoes.”

3. Learning the Craft and Respect for Acting

• Initial Self-Assessment: Not intimidated by most stage performances; sensed “a place here” in acting ([12:05]–[12:42]).
• Peggy Fury’s mentorship: She pushed him beyond his natural instincts, which were limited by his own life experience.
  • “I could be... natural. And that would be somewhat restricted to my own experience, meaning it wasn't going to play for... things very far outside of my own nature.” (Sean Penn, [13:09])
• Early Rejection: Fails an audition for “Kojak” but sees another actor (Barry Miller) play the part; realizes the difference is “freedom”—the capacity to improvise and embody. ([16:08]–[16:40])
• On Jeff Goldblum’s focus: Goldblum’s specificity onstage inspires Penn to “look at things” more deeply, a habit crucial for acting.

4. Process, Failure, and Success in Performance

• The Uncertainty of Acting: Tension and thrill in not knowing if a performance is working.
  • “There's always that tension of is it coming off or isn't it? ...I could be fucking up here badly, right?” (David Duchovny, [25:06])
• Subjectivity of Final Work: Editing shapes performances—sometimes directors “miss” what the actor intended; sometimes collaboration (e.g., Jack Nicholson in "The Pledge") adds magic.
  • “I probably took 75% easy, 75% of the adjustments that he made in the cut that I had presented him.” (Sean Penn, [27:41])
• The Relative Hardness of Acting vs. Directing: Acting requires “carrying the imaginary world... all day” and submitting to choices beyond your control.

5. Anecdotes of Artistic Integrity & Authority

• “Taps” Story: Penn, at 19, fights director Harold Becker over choreography—wants realism, refuses to stand up during a gunfight scene, only relents when promised both versions will be shot. In the end, the director’s version (which Penn doubted) is used, and a moviegoer confirms Penn’s instinct by yelling, “Hit the deck!” ([31:34]–[33:07])
  • “I'll never listen to a director again, no more bargaining.” (Sean Penn, [33:07]) (said with humor)

6. Iconic Roles and Creative Observations

• Spicoli (“Fast Times at Ridgemont High”): Penn saw the character as an “observation gig,” channeling dozens of real-life friends.
  • “They were all speaking the same Greek,” he jokes of the SoCal surfer scene. ([35:30])
• Artistic Takeaway: Sometimes success is capturing a subculture truly, not inventing it wholesale.

7. Lessons from Directing and Collaboration

• First Directorial Effort: Learns humility—“We learn how to make a movie by about the day we rap” ([36:42]).
• Observation: Even Scorsese seeks input, modeling continual learning and openness.
• Dream Projects: Both “Into the Wild” (Penn) and “Bucky Dent” (Duchovny) lived in their makers' heads for years—“10 years of subconsciously shooting the movie in my head.” (Sean Penn, [41:27])
• Living with Work: Both men confess to mentally “reshooting” their films after they’re finished; a game all artists play. ([41:34]–[41:56])
• Notable Moment: Duchovny shares an intimate story: Penn (rather than tear himself away from a screening of Duchovny’s film) “peed into a bottle” so as not to miss a moment, calling it “one of the most respectful things.” ([43:33]–[43:37])

8. On Brando, Masculinity, and the Nature of Failure

• Brando as a Role Model: Both see a sense of dissatisfaction and striving for “more” beyond acting in Brando.
  • “Is failure baked into the act of acting?” (Duchovny, [45:10])
• Penn’s Reflection: Brando respected acting yet grappled with its limits—Penn relates, blending his activism, writing, and public life into his identity.
• Dealing with Criticism & Hurt: Penn adapts; the hurt arises from misunderstanding, but present-day “fame belongs to everybody”—social media exposure is universal.
  • “The answer for me is you got to keep moving. Woodwork is a big one.” (Sean Penn, [51:25])
  • “There's a point at which your healing becomes your life. And, and so it's all just a joy to me. And I don't have time to read the bad things, but because I gotta get the sawdust out of my hair at the end of the day, and by that time I gotta have a few vodka tonics and call it a day.” ([51:46])

9. Shame, Reputation, and Self-Review

• Shame’s Role: Penn experiences shame “not when it’s illegitimate... It could be in a private act... when you fail... the obligation you have to your better self.” ([54:54])
• Navigating Reputation Today: It’s less about public opinion, more about aligning with your “future self”; guidance for kids is to “put on display where you're going” ([52:48], [53:43]).
  • “Affect your reputation as much as you can control, as much as you live it, whether it's misinterpreted and criticized or not in advance of your own vision...” (Sean Penn, [52:48])

10. On “Bob Honey,” Risk, and Audience Reception

• Duchovny reads from Penn’s book, discussing its deliberate provocations—Penn emphasizes he writes for those “in on the joke,” not to win everyone over. ([56:00])
  • “Are you in on the joke therefore able to giggle through the insanity of this or do you think the joke's being played on you?... That would maybe say something about the reader.” (Sean Penn, [56:47])

Notable Quotes & Memorable Moments

• On Squaring Away:
  • “I want a gravestone that legitimately says Sean Penn. A squared away individual with a square headstone.” — Sean Penn ([20:31])
• On Creative Freedom:
  • “He's free. And he's doing that. And I thought, you can do that.” — Sean Penn, on seeing Barry Miller act ([16:15])
• On Brando & Criticism:
  • “I just tell myself it's all true, and then it doesn't bother me.” — Marlon Brando, related by David Duchovny ([49:23])
• On Coping with Negative Attention:
  • “You got to keep moving. Woodwork is a big one.” — Sean Penn ([51:25])
• On Shame & Self-Review:
  • “We are under constant self review.” — Sean Penn ([55:22])
• On Reception to Art:
  • “You're engaging in wordplay... purposefully... creating a performance that's going to alienate people to not look closely enough at what you're really doing.” — David Duchovny, on Penn’s novel ([56:00])

Timestamps for Key Segments

• [01:14] – Duchovny on celebrity anonymity and magic in acting
• [03:10] – Duchovny introduces Sean Penn and premise of episode
• [05:50] – Penn’s early sense of accomplishment and “squaring away”; source of internal pride
• [09:50] – Anthony Zerby inspires Penn’s interest in acting
• [12:05] – Realization he belongs on-stage; not feeling inferior to established actors
• [13:09] – Peggy Fury busts him for relying too much on “natural” acting
• [16:15] – Watching another actor gives Penn “permission” to be free; pivotal craft insight
• [25:06] – The thrill and uncertainty of performance—could be failing at any moment
• [31:34] – Anecdote about his standoff with a director on “Taps”
• [33:24] – Duchovny on the impact of Spicoli and cultural archetypes
• [36:42] – Humility and lessons learned directing his first film
• [41:27] – Living with a movie for years, subconscious preparation
• [49:23] – Brando’s wisdom on handling public criticism
• [51:25] – Coping with hurt and misrepresentation; woodworking as therapy
• [54:54] – Shame, self-obligation, and internal review
• [56:47] – On writing provocatively and whether readers are “in on the joke”

Final Thoughts

This episode stands out for its unhurried, thoughtful exchanges that balance industry reflection with personal vulnerability. Listeners get a rare sense of both men’s inner lives and guiding philosophies, whether on parenting, enduring public scrutiny, or the mysterious craft of acting. The “squared away” motif becomes a metaphor for Penn’s (and perhaps Duchovny’s) foundation: striving for honest order in one’s private universe, even as the outer world remains noisy, unruly, and full of risk.

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