YOU MADE IT WEIRD with Pete Holmes — Michael Showalter (June 29, 2022)

Overview

This episode features a freewheeling, open-hearted conversation between Pete Holmes and Michael Showalter: comedian, writer, director, and member of the sketch groups The State and Stella. Their talk touches on Showalter’s career trajectory, the evolution of podcasting, creative process, boundaries, sobriety, spirituality, and the value of authenticity in both art and life. The tone is playful and candid, bouncing between inside-joke riffing and raw honesty.

Main Conversation Themes

• Evolving Roles in Comedy: From Actor to Director
• The Importance of Boundaries and Self-Discovery
• Process: Creativity, Control, and Collaboration
• Authenticity, Vulnerability, and Spiritual Growth
• Inside Jokes, Comedy Community, and Lasting Friendships
• Sobriety and Finding Meaning Beyond the Ego

Key Discussion Points & Insights

1. Podcasting, Video, and Comedy’s Changing Landscape

• YouTube Video Podcasts
  • Pete discusses adapting the podcast to YouTube and the initial fear it would harm the "intimacy" of the show. Showalter recalls one of the first DIY web shows: Tom Green’s basement show ([06:00–10:00]).
  • Showalter: “It was very like he was Colonel Kurtz and this was Apocalypse Now... I was being taken to the king.” ([07:01])
  • Vivid, comedic retelling of a surreal appearance on Tom Green’s show: blindfolded, weird energy, “entourage of young men”, a prank that “wasn’t a bit" ([06:20–12:10]).

2. Boundaries, Aging, and Valuing Self-Respect

• Modern Showalter: Wouldn’t go on a chaotic show again. “Modern day Showalter just would not have gone on it.” ([24:09])
  • Showalter opens up about how getting older allowed him to realize what situations or roles were right for him ([24:09–26:15]).
• Pete: “If you wanna get me excited, I don't care what car you drive. Tell me about your boundaries. Tell me about your self-respect.” ([24:09])

3. Acting, Auditions, and Knowing Your Place

• Showalter is candid about rarely landing roles as an actor unless he wrote them. “The only jobs I ever got were when I wrote it.” ([24:34])
• The feeling of not being “fully in your skin” in auditions vs. the confidence of actors who nail auditions ([25:14–26:22]).
• Showalter: “Good actors, real legit actors, they're fully in their skin when they're acting. I never once felt that way.” ([26:15, 32:09])

4. On Directing and Working with Actors

• Pete praises Showalter’s work on The Eyes of Tammy Faye ([27:37]).
• Showalter details his approach:
  • Meeting the actor where they are — different process with Jessica Chastain (“turns it on and off”) and Andrew Garfield (“somewhat of a method actor”) ([34:27–36:44]).
  • The “bubble” of a set — protecting an improvisational, trusting environment. “We’re in the bubble, we’re playing, we’re open, we’re raw. This has value. Nothing’s off-limits.” ([52:06])
• The myth of the “auteur” director:
  • Collaboration is key: “There’s 50 zillion people involved. You’re just one person… The director is just the host of the party, setting a tone.” ([48:19], [49:24])

5. Process: Planning vs. Discovery

• Admiration for directors known for total control like Wes Anderson, but also the art of letting the project unfold (Paul Thomas Anderson, Judd Apatow) ([38:38–42:11]).
• Showalter: “What I’m going for in the moment is just something that feels real… physical sense of like: That felt good. Let’s move on.” ([51:20])

6. Creative Joy and Care

• Both agree: the creative act should be a reward in itself.
  • “Let’s make something great. Let’s try to make it special. Let’s try to make it count.” ([53:16])
• Debate about “selling out” or caring less turns into advice about not being too precious, especially when family and real-world responsibilities kick in ([55:11–56:31], [60:09]).

7. Comedy Community, New York, and Shared History

• Reminiscing about East Village, NYC comedy, mutual friends (Kumail Nanjiani, Eugene Mirman, etc.), and the “scene” mentality—community support and pride ([57:34–59:59]).
• Anecdotes about early days, iconic venues, and how the scene influenced their views on taking “money gigs” ([56:05–60:10]).

8. Sobriety, Ego, and Spiritual Shift

• Michael discusses quitting drinking nearly 20 years ago—done solo, not through rehab. (“It was a spiritual bottom more than anything.” ([77:39]))
• He’s careful with his story: “The more I tell the story, the less meaning it has.” ([78:15])
  • Pete relates: “It starts becoming the story instead of what it was.” ([79:05])
• The “spiritual bottom” is described as, “I’m sick of being the center of the universe. I’m sick of the burden of everything being about me.” ([89:51, 90:08])
  • Letting go of ego: “The meaning of life... is to live and be a good person.” ([91:19])
  • Showalter likens ego loss to “the hole in the donut”—terrified he’d cease to exist, but discovering “you’re still here, so you must not be the thing that couldn’t do that.” ([95:05, 96:00])
• On religion: Pete thanks Michael for showing Tammy Faye’s faith as earnest—not zealotry. Michael, raised secular, shares how he’s found value in humility and interconnectedness ([85:45–93:50]).

Notable Quotes & Memorable Moments

• Michael Showalter, on podcasts:
  “It's supposed to feel like a sleepover. Like two bros in a basement. It's not supposed to be slick.” ([15:56])

• Showalter, on chaotic comedy:
  “I was afraid of Tom Green because at this time, he was in this kind of...very unpredictable phase.” ([07:38])

• Pete Holmes, on boundaries:
  “If you wanna get me excited, I don't care what car you drive. Tell me about your boundaries. Tell me about your self-respect.” ([24:09])

• Showalter, on authenticity:
  “It's literally authenticity. Yes, authenticity.” ([33:16])

• Showalter, on his spiritual bottom:
  “I’m sick of being the center of the universe. I’m sick of the burden of everything being about me.” ([89:51])

• Showalter, on ego and humility:
  “Ego deflation was the big thing for me... admitting that I'm not the center of the universe, that I'm not as great as I think I am, that everybody's awesome, everybody's fallible, it's not all about me.” ([91:19])

• Pete Holmes, on what matters in art:
  “The first step is declaring we’re gonna make something great or acknowledging the opportunity, the potential of making something great. I think that's the first step...” ([54:02])

• Showalter, on discovering he wasn't an actor:
  “I went and saw a play at Lincoln Center... I was joyfully watching it. And it occurred to me, like, I wonder if I should be thinking, 'I wish I was in this show.' And I wasn't...oh, you're not an actor.” ([74:14])

Major Segment Timestamps

• [04:19–13:06] — Tom Green story: Basement show, blindfold, comedic trauma, prank culture vs. real-life boundaries
• [24:09–26:13] — Boundaries, self-discovery, aging out of chaos
• [27:37–38:31] — Directing, acting vs. being “in your skin,” collaboration with actors, process of making Eyes of Tammy Faye
• [48:19–52:07] — The misconception of the auteur, director as host, value of collaboration
• [53:08–55:39] — Making things great vs. selling out, money jobs and creative care
• [76:10–78:51] — Sobriety, the “spiritual bottom,” dangers of making your story into a monologue
• [85:45–87:59] — Portraying religion honestly in film; not just zealotry, but earnest belief
• [89:51–96:41] — Spiritual journey, ego, humility, and the realization of interconnectedness
• [99:47–101:39] — Last time he laughed really hard: singing Toby Keith with Leo Allen and Eugene Mirman on tour

Comic Riffs & Running Bits

• Edit That Out / Keep It In: Recurring joke about on-air mistakes and editing bits, used for comedic effect ([37:17], [64:02])
• Apple Keyboard “Open Apple”: Dorky nostalgia about '80s/'90s computers and writing software ([17:17–18:26], callback at [106:30])
• Jizz as Slang: Pete proposes “jizz” as slang for “cool,” triggering a brief, silly riff ([29:39–30:13])
• Peer Group, Testimonials, and Crying: The pressure to have a good, emotional story in adolescence ([82:33–84:13])
• Inside Comedy Community References: Eugene Mirman, Kumail Nanjiani, NYC venues, “invite them up,” Luna Lounge ([57:34–59:59])

Closing/Plugs

• Showalter’s Recent Projects:
  • The Eyes of Tammy Faye (directed; Jessica Chastain & Andrew Garfield)
  • I Love That For You (Showtime, with Vanessa Bayer and Molly Shannon; executive producer, director) ([103:55–104:28])

Summary Takeaways

• Create with Care: Showalter and Holmes agree—the best work comes from intention, care, and a willingness to be present, not just to turn a profit or chase validation ([53:08 ff]).
• Boundaries Are Power: Learning where you thrive and drawing boundaries—personally and professionally—is a superpower that comes with self-knowledge ([24:09])
• It Takes a Village: Directing (and art in general) is a collaborative act, and the myth of the “auteur” is often just that—a myth ([48:19–49:20]).
• Sobriety, Spirituality, and Letting Go: Showalter’s journey reveals the freedom found when we let go of being the “center of the universe.” The process is deeply personal and best left a lived experience, not a story for performance ([77:39–91:19]).
• Comedy as Community: Both hosts reminisce about the power of scene, community, and shared experience—both as a source of joy and a place to learn humility ([57:34–59:59])

Final Words

“Keep it crispy.” – Michael Showalter ([106:46])

This episode is a testament to the creative life—a blend of weirdness, honesty, imperfection, growth, and the eternal search for belonging both on stage and off. Whether you’re in show business or not, Holmes and Showalter remind us: be generous, take risks, embrace your weird, and don’t be afraid to not be the center of the universe.