You Made It Weird with Pete Holmes

Guest: Joey Bragg
Release Date: October 4, 2023

Overview

In this episode, Pete Holmes sits down with actor and stand-up comedian Joey Bragg. Their conversation winds through Joey’s unusual journey from teenage stand-up in San Francisco to Disney Channel stardom and back to the stand-up grind. The two reflect on authenticity in comedy, managing self-worth and trauma in show biz, intergenerational weirdness, and the strange bonds formed over time in comedy. Pete and Joey’s rapport is built on years of intermittent contact, beginning with a heartfelt email Joey sent Pete at age 13—a pivotal moment for Joey’s path. The episode balances freewheeling humor, insightful shop talk, and genuine vulnerability about the challenges of growing up in entertainment.

Key Discussion Points & Insights

1. Weirdness, Vulnerability & The Comedy Industry

• Starting Young & Seeking Validation

  • Joey recounts starting stand-up at 13, driven by his love of comedy and inspired by movies like Funny People (50:04–51:10).
  • The sense of being an outsider—a young comic among adults—created both opportunity and resentment ("He's only getting gigs because he's young and cute... it's a gimmick." – Joey Bragg, 69:53).

• Their First Connection

  • At age 13, Joey emailed Pete, asking for advice—Pete replied with heartfelt encouragement (53:01–56:03).

    "I really hope you can help. Sincerely, Joey Bragg. P.S. if you do read this, please accept this friend request and I will send you some of my jokes so you could look them over."
    (Joey reading his email, 53:01)

  • Pete’s advice was basically: watch and perform as much as possible, start your own mic if needed, and be proactive.

• Comedian Culture & Jealousy

  • The environment Joey found was often laced with envy and competitiveness, especially as an outlier (70:09–71:38).

    "I have a really hard time... I'm gonna go up there and prove them that I deserve it." (Joey Bragg, 74:59)

  • Pete describes comedy open mics as a harsh but oddly supportive training ground, insisting everyone is terrible at first and that’s freeing (15:28).

2. Navigating Showbiz Trauma

• Disney Years: The "Prince" Treatment

  • Joey describes being thrust into a world of over-the-top kindness on Disney sets—what his mom called his “prince years” (60:57–61:35).
  • He contrasts the extreme support and attention in child TV stardom with the tooth-and-nail environment of stand-up.

• Crash to Earth: Losing the First Pilot

  • After missing out on his first show pilot, Joey fell into a depression, even skipping school for stretches and not recognizing it as real mental health struggle (68:25–69:10).

    "I would watch the Today show all day long and cry... I didn't know it was real depression at the time." (Joey Bragg, 69:06)

• Need for Therapy/Treatment

  • Pete and Joey both emphasize how formative (and potentially damaging) show business can be for young people, and how vital therapy is (61:41–61:57).

    "I'm a big proponent now... they should have a therapist on set for those kids." (Joey Bragg, 61:40)

  • Joey credits a therapist and a school for “depressed kids” with enabling him to more healthily process his experiences (97:28–97:43).

3. Self-Worth and the Shift in Perspective

• Struggles with Worthiness

  • Both discuss the long-lasting effects of seeking external validation from peers, and how essential it is to find self-defined criteria for satisfaction and success (102:03–103:06).

    "You need to establish your own... criteria for what a good life looks like." (Pete Holmes, 102:03)

• Comedy as a Calling, Not a Ladder

  • Joey and Pete celebrate finding joy in the act of stand-up itself, not just in money or career advancement (104:29).
  • The conversation also confronts the ways in which bitterness and scapegoating corrode a career, with Pete urging listeners to surround themselves with positivity and blinders to toxicity (78:56).

4. Comedy Shop Talk, Bits & Memorable Riffs

• Audition Stories and Regrets

  • Joey shares a hilarious and cringeworthy story about his Spider-Man audition (10:01–16:17). He regrets taking his shirt off in the audition, suspecting it cost him a spot.

    "I think I would be a millionaire if I just kept my fucking shirt on."
    (Joey Bragg, 14:35)

• Industry Satire

  • They riff on body positivity, casting, and industry “hot takes,” including faux-deep discussions of Mark and Donnie Wahlberg, and Pete’s claim:

    "I'd rather be Donnie than Mark every single day. Why every single day?"
    (Pete Holmes, 21:39)

• Cultural Commentary

  • Extended, absurdist rants about post-9/11 cultural changes, privacy/surveillance, and social media addiction (39:40–43:09).
  • Satirical breakdown of Borat, predicting its future cancellation (“Borat was never okay”—Pete Holmes, 24:44), and its impact on Kazakhstan natives (26:17–26:30).

• Bit Highlights & Riffs

  • Adult arcades, porno theaters, Pac-Man sexual positions (“Score is always 69” – Pete Holmes, 38:42), old people addiction to mail and obsessing over tiny hobbies for “ADHD” (112:04).

5. Philosophy & Big Picture Reflections

• Mission Statements and Meaning
  • Pete elevates the discussion to the existential, encouraging listeners to determine what brings them true peace, contentment, and joy, not to be ruled by the arbitrary standards of “gatekeepers” (99:05–100:23).

    "You can set the mission statement for your own life instead of letting these lunatics establish it." (Pete Holmes, 100:19)

• Therapy, Trauma, and Acceptance
  • Both guests speak candidly to the reality that “your trauma is your trauma,” regardless of how "serious" others might find it (83:54).
  • Joey credits therapy for helping him undo mental knots, and says he now does stand-up for love, not status (94:56).

6. Quick-Fire & Playful Closing

• UFOs & Near Death
  • Joey relays seeing a true UFO while driving late night near a military base, and a terrifying airplane emergency landing (105:25–107:49).
• Family, Aging, and Laughs
  • Hardest times laughed: Joey says no one gets him giggling like his mom, riffing on making fun of her for turning 60 (109:51–111:22).
• Final Affirmations
  • Pete closes with warmth, telling Joey:

    "You're valid. You're valuable... You're okay. You're doing well." (Pete Holmes, 112:30)

Notable Quotes & Timestamps

• On adversity in comedy:

  "I get so much of my confidence by realizing how bad other people are at it."
  (Joey Bragg, 15:17)

• On trauma and the business:

  "I just stopped going [to school]... I would watch the Today Show all day and cry."
  (Joey Bragg, 69:06)

• On therapy & growth:

  "I credit so much of my perspective from just being able to talk to somebody that's removed from it."
  (Joey Bragg, 97:43)

• On defining your own path:

  "You can set the mission statement for your own life instead of letting these lunatics establish it."
  (Pete Holmes, 100:19)

• On connecting with inspiring people:

  "I would not have the career and life that I have right now if you hadn't sent that."
  (Joey Bragg, 57:42)

• On the purpose of comedy:

  "Stand up life and just a regular good life have a lot of things in common. It's figuring out what brings you into peace and… at home in your skin."
  (Pete Holmes, 105:08)

Episode Structure & Timestamps

• [03:12] – Joke riffing, Catstronauts, space animals, Marvel’s Cosmo, dark animal comedy
• [10:01]–[16:17] – Joey’s Spider-Man audition and “shirt off” story
• [53:01]–[56:03] – Joey reads his 13-year-old fan email to Pete; Pete’s advice; reflection on their early connection
• [60:34]–[63:02] – Disney Channel “prince” years, pilot disappointment, importance of therapy
• [68:25] – Joey’s depression post-pilot failure and school avoidance
• [69:53]–[80:22] – Feeling like an outsider in comedy, confronting the jealousy of peers, seeking validation, learning hard lessons
• [97:28] – Ongoing therapy and processing long-term effects of childhood fame/trauma
• [102:03] – The importance of creating your own mission statement/criteria for success
• [105:22] – Fun speed round: ghosts, UFOs, near-death, hardest laughs in life
• [112:30] – Pete affirms Joey ("You're valid. You're valuable.") and closes the episode

Tone

• A welcoming, open-hearted blend of insightful shop talk, silly riffing, and tender vulnerability. Pete and Joey move between satirical bits and genuinely empathic, emotionally aware conversation, staying true to the spirit of “making it weird”—amplifying oddities, insecurities, and the universal struggle for identity and belonging.