You Made It Weird with Pete Holmes

Episode: Max Silvestri Returns

Release date: December 10, 2025

Overview

This episode of "You Made It Weird" features comedian, writer, and showrunner Max Silvestri returning to the podcast for a candid, funny, and thoughtful conversation with Pete Holmes. The two old friends dig into the inner workings of comedy, the oddities of podcasting, what it means to perform authenticity, and how life and career changes (especially parenthood and loss) have shaped them. They also discuss Max’s new projects, including the HBO series "I Love LA", and share stories about the evolution of the comedy scene and how technology and culture have transformed creative lives.

Main Theme: Exploring the emotional and professional pivots of midlife, friendship, podcast culture, comedic persona, and creative growth—peppered with confessions, laughter, and big life moments.

Key Discussion Points

Reconnecting and Life Updates

• Reunion in the Studio: Max and Pete reminisce about how long it's been since they last connected in person (03:06–04:00).
• Mutual Respect and Career Evolution: Pete introduces Max, expressing deep admiration for his comedic talent and kindness, noting their 20+ year friendship and Max’s multi-faceted career (00:18).
• Parenting and Loss: Max reveals the impact of becoming a father to his son, Waylon, and details the trauma and aftermath of losing his family home to a fire (19:33–42:54).

The New Podcast & Creative Partnerships

• Podcast Genesis: Max discusses launching the new podcast "I Need You Guys" with Gabe Liedman and Jenny Slate, prompted by life logistics and the desire to keep their friendship alive despite geographic distance (05:02–07:44).
  • Format talk versus freeform riffing
  • The practicalities of remote recording and including guests
• Podcast as Friendship & Commerce: Both reflect on how podcasts, while commercial ventures, are modern manifestations of classic social rituals (10:00–12:29)

“The more things change, the more they stay the same. People just want to hang out... you end up using the flavor of the times, podcasting, to encourage what you would have done in 1911, which is, like, gotten together and had a jazz coffee.” —Pete Holmes, 10:36

Personas, Authenticity & the Performance of Life

• Comedy Persona Transparency: Max and Pete compare their on- and off-air selves, noting how hosting evolves to become more authentic, especially when close friends or a spouse is involved (13:47–15:25).

“I’m almost barely hosting. I’m allowing your energy to inform me, and then we’ll see what happens with us together.” —Pete Holmes, 14:00

• Frontstage/Backstage Dichotomy: Inspired by Gia Tolentino’s concepts, they discuss how social interactions, relationships, and even marriage involve the “backstage” self—while most of life involves some performance (15:45–17:03).

Trauma, Community, and Grieving

• Losing a Home: Max’s harrowing account of the fires that destroyed his house and the emotional complexity of being “the victim” (24:38–42:54).
  • Evacuating in the middle of the night (29:51–34:48)
  • The way trauma reorganizes memory, marking life into “before” and “after” (27:32–29:49)
  • Navigating community and grief groups for new parents affected by the fire

"It was wild to experience the event that you are almost sure would be the organizing event of your memoir." —Gabe Liedman, 26:34

• Grieving Stuff and Identity: They talk about objects and place as extensions of self, the fantasy of “reinvention” after a loss, and the reality of that process (41:58–43:22).
• The Burden of Others' Reactions: How others’ attempts to help after trauma can create additional emotional labor (38:17–39:44).

Comedy Culture, Critical Voice, Ego, and Aging

• Evolution of Stand-up Persona: They examine how the “coin of the realm” in comedy is having a take—sharp, fast, sometimes biting—and how this can be both a talent and an exhausting habit, especially as they get older and become parents (49:00–53:20).
• They discuss intentionally slowing down, cultivating more curiosity, and balancing the snap judgments that comedy prizes with empathy and patience.
• Reflections on Generational Change: How younger comedians and “influencers” operate differently, what youth and image as currency mean today, and how older comics' perspectives shift (58:32–62:39).

“You don’t get to sell and make a show on HBO at 29 unless you work really hard to get it. You have to work when you have a moment—youth as a currency expires.” —Gabe Liedman, 66:06

Modern Comedy, Technology & Self-Promotion

• The Social Media & Clip Economy: The merits and neuroses surrounding sharing stand-up online, old myths about "saving material," and how connection—rather than perfection—is now key (71:13–73:02).
• Comedy Scene Nostalgia: Stories about submitting photos to comedy blogs, early-career hunger, and pranking John Mulaney for the comedy blog “The Apiary” (73:10–76:04).

Memorable Stories & Reflections

Losing the House: The Fire Story

• Haunting Real-Time Decisions: Deciding whether to evacuate, gathering “just weekend stuff,” and the surreal, polite logic in an impending crisis (29:51–33:29).
• Processing Trauma through Humor: Jokingly comparing the fire’s destruction to the “Blitzkrieg” and keeping things riffable as a means of coping (28:45–28:59).
• Aftermath and Support: Finding solace in a trauma group, the emotional weight of not just losing possessions but comforting others (37:12–39:44).

Comedy Life: Advice and Influence

• Marking Each Other: Max recalls advice and jokes Pete gave him that stuck, reflecting on the odd way old friends' feedback can clarify your comedic voice (44:54–46:32).

“You always felt like...you had a real Persona. You had come in from Chicago, like, pretty fully formed...But you had some compliment on my set, and then you said, I feel like I could write for you now.” —Gabe Liedman, 45:13

Industry Paranoia & Pranks

• The Apiary Story: Gabe recounts getting threatened by a disgruntled Rhode Island comic years after a critical interview, highlighting the weird dangers (and repercussions) of early-career candor and the permanence of online archives (78:05–86:07).

Notable Quotes

• “Our podcast is really a way to keep our friendship together. We’ve always brought this energy. But guests are nice, because otherwise it’s just mining in the same direction every week.”
  —Gabe Liedman, 08:04

• “You mine a different vein, that’s all. ...With guests, you distract yourself from the exploit—not the exploration.”
  —Pete Holmes, 08:27

• “I like having takes, but sometimes I clock myself in my relationship, like, I have the meaner or more confident version of myself on, and it’s not honest. It’s just the coin of the realm.”
  —Gabe Liedman, 49:00

• “We’re in the business of making snap judgments and takes. But as a dad, now I’m interested in being open, curious, slow to judgment. Nobody likes these things unless you’re paying them to make you laugh.”
  —Pete Holmes, 50:44

Important Timestamps

| Timestamp | Segment/Event | |-----------|--------------| | 03:06–05:00 | Max and Pete reconnect and reminisce about years in LA, overlapping at shows | | 05:02–07:44 | Launching "I Need You Guys" podcast—a behind-the-scenes look | | 10:00–12:29 | Podcasting as modern friendship, the irony of scheduling and monetizing hangs | | 19:33–24:38 | Gabe on becoming a dad; introduction to the fire story | | 24:38–34:48 | Detailed retelling of the fire evacuation, loss, and immediate aftermath | | 37:12–39:44 | Grief groups, the burden of others’ reactions after trauma | | 41:58–43:22 | Possessions, reinvention fantasy, and post-loss identity crisis | | 49:00–53:38 | Comedy persona, 'coin of the realm,’ and how comedy habits creep into personal life | | 58:32–61:59 | Writing for new perspectives, moving from satire to understanding, discussing "I Love LA" | | 66:06–67:29 | Youth, beauty, and success as currency—navigating the influencer era | | 71:13–73:02 | Stand-up in the digital era, sharing online and shifting expectations | | 73:10–76:04 | The “Apiary” prank/joke legacy—photo submitted by John Mulaney | | 78:05–86:07 | The "Apiary story" — Gabe’s cyber-angry prop comic, online permanence, and repercussions |

Tone & Language

• Conversational, honest, comedic: Pete and Max riff freely, tease, reminisce, and occasionally dive deep, always returning to humor.
• Reflective, vulnerable: Particularly in discussions about loss, parenthood, and growing older.
• Insider-y but inviting: Plenty of context for listeners who don’t know every name, but lots of inside jokes and references for comedy nerds.

Final Thoughts

This episode blends the funny and the sincere, offering rare glimpses into the personal growth and challenges that shape comedians beyond their stage personas. It's rich in both belly laughs and true vulnerability—showcasing the creative, awkward, and painful processes through which comedians adapt, age, and deepen their art and lives.

Check out:

• Max’s HBO show "I Love LA" (Sundays, HBO)
• The new podcast with Gabe Liedman and Jenny Slate, “I Need You Guys.”

“Keep it crispy.” —Gabe Liedman, 91:14

For More:

• Follow Max Silvestri and Pete Holmes on socials
• Links to projects via their respective accounts and show notes