The Rich Roll Podcast

Episode: Jay Duplass & Michael Strassner On The Art of Creative Rebellion

Date: September 1, 2025
Guests: Jay Duplass, Michael Strassner
Host: Rich Roll

Overview

In this heartfelt, funny, and deeply authentic episode, Rich Roll sits down with filmmaker Jay Duplass and comedian-actor Michael Strassner to explore the making of their new indie film, Baltimore Ons. The conversation becomes a powerful meditation on creative risk-taking, addiction and recovery, artistic collaboration, and the enduring importance of real human stories in an age of media overload and cynicism. The trio cover everything from vulnerability, sobriety, and creative process, to the shifting state of the film industry—forging a space of radical honesty and encouragement for aspiring artists everywhere.

Key Discussion Points & Insights

1. The Story Behind Baltimore Ons: Art from Life

Timestamp: [03:28] – [14:25]

• Early Sobriety in Film:

  • Jay describes how the movie is set during the main character's first six months sober—a rare focus, as most addiction stories climax with getting sober, not the tough, uncertain aftermath.
  • The narrative draws directly from Michael’s personal experiences, including his fear that sobriety would cost him his comedic gift.
  • Michael shares his own suicide attempt—and how the failure of that moment became a turning point for recovery and asking for help.
    • Quote (Michael Strassner, [04:20]):

      "I was downstairs in my basement and my best thinking was, I don't think I want to be here anymore, you know? So I tried to hang myself and luckily the belt broke and the next day was the first day I actually asked for help."

• Jay's Creative Roots:

  • Rich recounts his own indie film history and emotional investment in the Duplass brothers’ rise, beginning with their early film The Puffy Chair.

2. Creative Rebellion: “Make Movies, Not Meetings”

Timestamp: [17:26] – [25:48]

• Indie Film Against the Odds:

  • Jay underscores how rare it is for a tiny, star-less indie like Baltimore Ons to get a theatrical release—calling it a "bizarre unicorn."
  • Recalls his and his brother Mark's philosophy:
    • Quote (Jay Duplass, [20:59]):

      "We even had a philosophy around it...make movies, not meetings. Because even when you get involved in Hollywood, they just want to talk about stuff."

  • The need to self-start projects and not wait for studio permission:
    • Quote (Jay Duplass, [32:06]):

      "Calgary isn't coming."

• Jay & Michael's First Meeting:

  • Their collaboration emerges from Instagram—Michael’s comic videos catch Jay’s eye, leading to mentorship and then co-creating the film.
  • Revealing stories around their mutual support, sharing scripts, and rooting the film in authentic, lived experience.

3. Filmmaking as Service & Vulnerability

Timestamp: [28:20] – [36:14]

• Serving the Audience:

  • Jay intentionally centers the film on serving and uplifting others, not personal glory.
  • The crew's genuine emotional investment created a rare, energizing creative environment.
    • Quote (Jay Duplass, [30:16]):

      "The experience of making the movie together was for us the way that I think the audience is experiencing the movie. ...we are the manifestors of our own destiny."

• Taking Creative Risks:

  • Everyone involved in the film made major sacrifices—motivated by love, personal history, and the hope to bring beauty into the world, not profits.

4. The Sobriety Origin Story: Comedy, Loss, and Redemption

Timestamp: [40:05] – [54:57]

• Michael’s Addiction and Artistic Dreams:

  • Details about growing up in Baltimore, early substance use, striving to become a comedian—and the spiral of addiction amid professional disappointment (not making SNL, losing his improv group).

  • Turning point: after Groundlings asked him to take a leave and get sober, Michael enters recovery, aided by AA and supportive strangers.

  • Sobriety’s Fragile Miracle:

    • Both guests note how unexpected lows (rejection, being fired) are often fate’s way of pushing artists toward their true calling and growth.
    • Quote (Jay Duplass, [54:15]):

      "It's also an incredible lesson in the idea that the worst thing that could happen to you is maybe the best thing that could happen to you."

5. Finding Creative Community and Building a Film

Timestamp: [59:20] – [64:16]

• Family, Authenticity, and Grounding:

  • Casting real family members and friends—grounding the process, reinforcing the authenticity of Baltimore as a character, and providing emotional support.
  • Michael discusses the loss of his brother Zach to addiction, and the bittersweet, motivating power of that legacy.

• Performance and Restraint:

  • Rich notes that Michael’s comedic performance has a necessary restraint—avoiding showiness and letting humor emerge organically from story and character.
    • Quote (Rich Roll, [64:16]):

      "It just felt like a less mature performer given this opportunity would be like, you know, kind of, okay, I'm gonna go, I'm taking it all the way...there was that sense of like, this guy could probably, you know, push the accelerator on this and he's not doing that."

6. Sustaining Creativity, Facing Fear, and Evolving Careers

Timestamp: [69:47] – [79:46]

• Jay’s Workaholism, Family, and Evolution:

  • Insights into Jay’s running habit, family life, work overload, and eventual recalibration as he ages.
  • Both Jay and Mark’s creative journey: from VHS homemade films and outsider status to launching a DIY movement (mumblecore) and influencing a generation.

• Persistence & Attrition over “Overnight Success”:

  • The myth of overnight success is dispelled—real achievement is a product of attrition, perseverance, and loving the actual process.
    • Quote (Jay Duplass, [32:59]):

      "It's never an overnight success story. It's attrition. It's forging forward when all the signs even tell you you shouldn't be successful."

7. Collaboration, Feedback, and Directorial Philosophy

Timestamp: [105:06] – [114:27]

• The Collaborative Process:

  • Jay discusses balancing a director’s vision with input from cast and crew, and his “benign dictator” philosophy—asserting control while creating space for contributions.
    • Quote (Jay Duplass, [107:21]):

      "The best movies are made by dictators who are very benign and who include everybody else in the process.”

• Art Belongs to the Audience:

  • Over time, creative control is relinquished—the finished film belongs to the viewers:
    • Quote (Jay Duplass, [109:17]):

      “At the very end, the movie no longer belongs to us...if it doesn't belong 100% to a stranger in a dark room that you will never have a conversation with, you're not really doing your job.”

8. The State of Storytelling and Indie Film

Timestamp: [137:12] – [143:52]

• Yearning for Real Human Stories:

  • Rich and Jay critique the dominance of superhero and franchise films—arguing that our cultural mythology has become impoverished and escapist.
    • Quote (Jay Duplass, [138:02]):

      "Our cultural mythology is broken. ...our cultural mythology in America right now is represented in a superhero movie. ...Nothing could be more broken. ...I think the superhero movies feel really good in the moment, and then you go home and they just feel so far away. They're not really nourishing the soul in a way that stories can."

• Role of Indie Film:

  • The necessity of films that show flawed, relatable people—and the vital role of authenticity and vulnerability in healing culture and individual lives.

9. Advice for Aspiring Artists and Creators

Timestamp: [145:10] – [151:41]

• Persistence & Embracing Failure:

  • Michael and Jay both stress the importance of not giving up: fail, repeat, keep going, and know that all it takes is one "yes."
    • Quote (Michael Strassner, [145:10]):

      "It takes one person in the field of Hollywood to be. Yes. ...fail, fail over and over again, get back up, fail, fail some more. But just know that, like, no matter what...just do it and not worry about what other people are telling you to do or not do."

• Honesty & Making Art for Its Own Sake:

  • Jay counsels aspiring filmmakers to "make bad art, a lot of it," emphasizing the necessity of practice, process, and internal truth over external recognition.

    • Quote (Jay Duplass, [85:26]):

      "Just make bad art. Make a lot of bad art."

  • The reward is found in the work and in the expression of one's authentic voice, not in the validation or social proximity to success.

    • Quote (Jay Duplass, [151:09]):

      "It's less about making art and more just about Me being true to myself and just witnessing how much art is going to come out of that, because I'm not really interested anymore in forcing art because that creates collapse."

Notable Quotes & Memorable Moments

• On Sobriety & Creativity:

  “The first book I read when I got sober was the Chris Farley Show. ...If he could do it, maybe I could do this.”
  — Michael Strassner ([49:51])

• On Collaboration:

  “He just said, you’re enough, like you’re great. Just stay in it.”
  — Michael Strassner, on Jay's best direction advice ([64:23])

• On Family & Authenticity:

  "The coolest thing about doing that whole [movie] was having my family next to me and watching this movie that we worked so hard on.”
  — Michael Strassner ([59:20])

• On the Power of Story:

  "Joseph Campbell said stories are equipment for living. ...a story is a way to change people's minds and change people's culture."
  — Jay Duplass ([138:02])

• On the Journey:

  "I absolutely love my life today, and I was this close to missing it all."
  — Michael Strassner ([147:39])

Selected Timestamps for Important Segments

• [03:28] – Michael’s early sobriety, suicide attempt, and personal story
• [17:26] – Jay on indie films, working philosophy: “Make movies, not meetings”
• [28:20] – Filmmaking as service and earnestness, creating authentic films
• [40:05] – Michael’s addiction, comedy beginnings, path to recovery
• [54:15] – On career setbacks becoming gifts, and the pain of artistic rejection
• [69:47] – Jay on running, work obsession, creative roots
• [85:26] – Jay’s advice on making lots of bad art and the myth of overnight success
• [109:17] – Jay on letting go—art belonging to the audience
• [138:02] – Critique of superhero movies and the need for real, human stories
• [145:10] – Advice to aspiring creators: fail, persist, embrace the unknown
• [151:09] – Jay on living in truth and not forcing art

Conclusion

This episode is a masterclass in the art of creative rebellion, vulnerability, and the persistent, messy work of self-actualization. Through candid storytelling and humorous details, Jay Duplass and Michael Strassner—guided by Rich Roll’s generous, empathetic interviewing—show how authenticity, risk, and an open heart can transmute pain into purpose. For anyone chasing a creative life, grappling with personal demons, or searching for inspiration, this conversation is a generous, essential listen.

[The film “Baltimore Ons” is released theatrically this fall. For more on Michael’s family foundation in his brother’s memory: ZTP Foundation.]