You Made It Weird with Pete Holmes

Guest: Blair Carlisle (Uncle Pappy)

Date: January 21, 2026
Theme: The Philosophy, Weirdness, & Reveal Behind Uncle Pappy: How a Young Improviser Created Social Media’s Favorite Old Man Sage

Episode Overview

This episode is a delightful deep dive into the story of "Uncle Pappy"—the sunshiny, mustachioed, shirtless old man from social media who dispenses daily wisdom and positivity and is, in reality, 30-year-old improviser Blair Carlisle. Pete and Blair discuss anxiety, wisdom, addiction, creation of persona, forgiveness, suffering, and why growing up doesn’t have to mean losing your “weird.” The episode also marks Blair’s first in-depth public reveal as the person behind Uncle Pappy, exploring themes of authenticity, generational wisdom, and the secret weirdness in everyone.

Key Discussion Points & Insights

1. Blair’s Journey: From Snapchat Filter to Social Media Phenomenon

• Origin of Uncle Pappy ([86:00-89:10])
  • Uncle Pappy started as Blair playing with an old man Snapchat filter, making silly videos for friends:
    • "This is gonna be very underwhelming and disappointing. Probably. Like the meaning of life… Pappy is just a Snapchat filter." (86:05, Blair)
  • Friends urged him to post daily; within a few videos, one went viral.
  • Early Pappy: a comedic, somewhat satirical “Florida man” with big energy and a patriotic (even anti-English) persona.
  • After a Ben Shapiro reaction video, Blair re-examined the character's impact:
    • "Ben Shapiro, who I’m not a big fan of ... was just giggling at my video... It was the first time I had to grapple that people were watching me.” (90:02, Blair)
  • This reflection prompted a shift away from satire/negativity towards the wholesome, philosophical Pappy known today:
    • "Even comedic negativity is still negativity." (91:30, Blair)

2. The Philosophy of Uncle Pappy: Avatars, Inner Wisdom, and Suffering

• Pappy as Higher Self/Ego Work ([08:32-10:53])

  • Blair describes Pappy as his “best friend”—and the avatar for the best, gentlest version of himself:
    • “He’s become my best friend almost... If I’m the person I want to be, it’s that guy.” (08:38, Blair)
    • “Make your higher power the best version of you.” (10:26, Blair)
  • Pete draws lines between therapy, higher self, spiritual "avatars":
    • “A lot of inner work involves conjuring ... your higher self. That’s been the standard for therapy for decades.” (08:51, Pete)

• Real Wisdom Isn’t Age—It’s Suffering & Reflection ([57:59-58:45], [108:47-109:27])

  • Blair, who’s dealt with depression since age 13, emphasizes that suffering is often the price of real growth and empathy:
    • “Pain is the price of wisdom ... you have to suffer for most forms of wisdom.” (58:12, Blair)
    • “There’s a lot of old people who aren’t wise ... And there’s a lot of young people who are ten times wiser than any old person I’ve known.” (109:01, Blair)

• Creating and Maintaining Wholesome Internet Spaces

  • Blair intentionally rerouted Pappy’s persona from patriotic antagonism to positivity after realizing satire, even when ironic, perpetuated negativity online:
    • “I don’t want to do this anymore. I don’t want to make people feel bad. Even comedic negativity is still negativity.” (91:30, Blair)
  • Pete relates to the sense of responsibility:
    • "It's your persona, but it's still hard to be like that all the day, all the live long day." (91:34, Pete)

3. Anxiety, Performance Jitters, and Using Humor (and Characters) to Cope

• Pre-Show Anxiety & “Coyote Mode” ([05:24-07:41])
  • Both discuss pre-performance nerves and use the metaphor of "coyote mode"—body vigilant for danger even without real threat.
    • Pete: "The body doesn’t listen... the brain says, we got this, and the body goes, I don’t know." (07:12)
    • Blair: "It’s like, evolutionarily, your body’s like, a predator might come get us right now. And it's like, no, I’m just gonna go on a podcast; a tiger isn’t gonna kill me right now." (07:41)
  • Watching Uncle Pappy helps both Blair and Pete "lighten up" and reframe stress.

4. Addiction, Alcohol, and Reclaiming Joy (without Substances)

• Blair’s Sobriety Story ([10:00-46:41])

  • Quit drinking after seven years of functional, nightly drunkenness; shares details of addiction, withdrawal, and the allure of escapism:
    • “First time I ever got drunk … I looked in the mirror and said, 'Don’t ever not feel like this.'” (39:53, Blair)
  • Alcohol’s marketing lies: equating “ritual” or relaxation to substances. Pete:
    • "They somehow co-opted just the idea you might be sitting enjoying a moment." (37:41)
  • Recovery wisdom: “Life isn’t broccoli. ... Life is dessert, too.” (40:41, Blair)
  • Why moderate drinking never made sense: "If there’s something that makes you feel a way you like, then drink all of it." (48:13, Pete)

• Transition to Content with Purpose

  • Sobriety, therapy, philosophy journaling, and a desire to inject something positive into the world led to Uncle Pappy’s shift:
    • "I remember thinking, this will probably make me lose followers … but I just started talking about the stuff that I journal about." (93:03, Blair)

5. Grace, Forgiveness, and Dealing with Irritating People (and Ourselves)

• Forgiving Reality, People, and Ourselves ([21:03-23:46], [24:32-25:38])
  • Borrowing from David Foster Wallace, Richard Rohr, and Buddhist parables, Pete and Blair discuss "forgiving reality"—not just forgiving people, but forgiving that things are as they are:
    • Pete: “Richard Rohr calls it ‘forgiving reality’ ... the first forgiveness is to forgive reality.” (22:01)
  • Blair: “It reminds me of the Buddhist story … he yells at the other boat, and the fog clears, and the boat’s empty. Why does it matter if the boat is empty?” (23:04)
• “It's Just Your Turn” ([18:05-19:32])
  • Emphasizing empathy and perspective—they recount teaching kids to have grace ("I've made that same mistake") and use the metaphor of annoying people as "better tennis players" who help us grow.

6. Mortality, High School Reunions, and the Common Human Experience

• Death, Humility, and Growing Up ([25:09-28:36])

  • High school reunions as microcosms of spiritual reunification—everyone, regardless of role, softens and says, “We were just trying our best.”
    • "It reminded me so much of, man, after we all die, we're all gonna be ... ‘I took stuff really seriously back then…’" (25:22, Blair)
  • Life is suffering, but suffering can create wisdom, connection, humility.

• On Death as Returning to Wholeness ([71:15-72:10])

  • "I think about death kind of like a lizard... death is the person trying to catch it and put it back outside ... The lizard doesn’t understand, and that’s how I kind of feel. We run from death... death’s like you’re not supposed to feel separate from everything." (71:15, Blair)

7. Uncle Pappy’s Ethos: Youthful Wisdom, Environmentalism, and Owning the Weird

• Being Young, Wise, and Purposeful ([108:47-111:55])
  • Blair hopes the Uncle Pappy reveal gives young adults permission to own their wisdom:
    • “People, young people, are worth listening to ... this is your world. Everybody’s faking it. Even the old people." (108:47, Blair)
• Environmental Advocacy and the Next Chapter ([104:24-105:44])
  • Blair’s “real” life as a law student and environmental advocate is feeding upcoming work—partnering with organizations to promote unity around protecting nature.
• Authenticity and the Courage to Try ([96:10-99:16])
  • Pete and Blair riff on cultural embarrassment about “trying”—whether making videos or living enthusiastically.
    • "Why is it embarrassing to try? Fail faster. Get some fails under your belt." (96:33, Pete)
    • "Why is it more embarrassing to be sharp than flat?" (97:18, Blair)

8. The Reveal: Blair is Uncle Pappy

• How Will Fans React? ([123:21-124:04])
  • Pete and Blair are optimistic that fans will accept the character as a mask/vehicle for joy rather than a deception:
    • "If I got a cameo from you and I knew it was you doing Pee Wee or Batman, I'd be fine. Nobody thinks you're Batman." (123:49, Pete)
    • "It does put people off, then I understand that too. But I'm still gonna make Pappy videos … He’s my best friend. I love hanging out with him." (124:04, Blair)

9. Notable Quotes & Memorable Moments

• On Higher Selves
  • "There's a version of you, even if you are tripping up … that knows what you want. Lean on that." (09:43, Pete)
• On Forgiveness
  • "The first forgiveness is to forgive reality." (22:01, Pete)
• On Suffering and Wisdom
  • "Pain is the price of wisdom." (58:12, Blair)
• On Growing Older
  • "The older you get, the less free will you have. That window is getting smaller." (110:34, Blair)
• On Trying and Failure
  • "Fail faster. Get some fails under your belt. We need to normalize trying and having fun and being excited." (96:33, Pete / 96:44, Blair)
• On Coming Out as Pappy
  • "I want to hammer home … that young people are worth listening to too." (108:47, Blair)

Timestamps for Major Segments

-00:00 – 05:00: Intro, tour dates, Uncle Pappy’s background -05:00 – 10:50: Anxiety, performance nerves, coyote mode, using comedy/self-skewering to cope -11:00 – 23:46: Spiritual avatars, philosophical influences, higher self, forgiveness, David Foster Wallace’s “default setting” -24:00 – 35:00: Vulnerability, death, high school reunions, humility, human interconnectedness -39:53 – 47:03: Blair’s addiction story, alcoholism as chasing joy/relief, functionality vs. denial -86:00 – 107:42: Deep dive on the creation and evolution of Uncle Pappy, the social media character, and using a platform for good -108:47 – 111:07: Age, wisdom, generational imposter syndrome, why young voices matter -123:21 – 124:04: Handling the reveal, authenticity, and faith in the Pappy audience

Key Memorable Moments

• [13:36] "I have a very vivid memory being on a family vacation in high school and thinking I have to figure out how to be on You Made It Weird before Pete Holmes stops doing it.” — Blair on his “manifestation”
• [22:01] "Richard Rohr calls it ‘the first forgiveness is to forgive reality’ and I was like, that goes past my brain and to my heart." — Pete
• [39:53] “First time I ever got drunk … I looked in the mirror and said, 'Don’t ever not feel like this.'” — Blair
• [91:34] “Even comedic negativity is still negativity.” — Blair, on transforming Uncle Pappy’s content
• [123:37] "If I got a cameo from you and I knew it was you doing Peewee or Batman, I'd be fine. Nobody thinks you're Batman." — Pete

The “Weirdest” and Funniest Moments

• [87:10] “I’d make Snapchats being like…I’m gonna eat this manatee. Like, being like a crazy Florida man.”
• [46:07] “If you say ‘izzle’ three times in a mirror, Snoop shows up. You’ll smell him first... It’s a weed joke.”
• [133:29] Choir horror story: “There’s eight of us and it sounds so, so bad…” (leading to uncontrollable laughter on stage)

Closing Notes

Blair’s reframe of his now-famous character is a perfect Weirdism—a young person embodying the sage, dispensing sometimes silly, always sincere wisdom in a shirtless, lagoon-floating avatar. Pete’s generous, philosophical approach gives both the “reveal” and the wisdom shared real weight. This is an episode that celebrates secret weirdness, personal transformation, and the joy of “failing faster,” learning, and making something genuine—even if it starts as a Snapchat joke.

Final sign-off (in classic Weird fashion):
Blair (as Pappy): “Hey there, man ... even when life gets down and you’re in your job time, keep it crispy, people. Keep it crispy!” ([134:21])

For Further Listening

• See show notes for Blair/Uncle Pappy’s platforms and Pete’s tour dates at PeteHolmes.com
• Featured wisdom: Richard Rohr, David Foster Wallace, Mr. Rogers, Ramana Maharshi

Summary prepared for those who want the deep weird, the hidden wisdom, and the uplift of both Pappy and Pete—without any sponsored sizzle.