You Made It Weird with Pete Holmes – Steven Wright (December 4, 2024)
Main Theme:
A rare, intimate conversation between Pete Holmes and legendary comedian Steven Wright, exploring the philosophy, process, and weirdness of comedy, creative rhythms, and life’s mysteries through their distinct sensibilities.
Episode Overview
In this special episode, Pete Holmes sits down with Steven Wright, one of his comedic heroes, for a conversation marked by warmth, humor, and philosophical musings. The discussion weaves through how jokes are constructed, the role of the subconscious in creativity, the arbitrary nature of audience response, influences, the Boston comedy scene, and the existential weirdness of being human. Both comedians share personal stories and reflect on the profound oddity of everyday existence, delivering insights for comedy fans and fellow weirdos alike.
Key Discussion Points & Insights
1. Serendipitous Origins of the Conversation
- Pete and Steven ran into each other at Boston Logan Airport, sparking an unusually spontaneous connection for both, eventually leading to this podcast appearance.
- Steven Wright (07:09): “It was only like two days ago, right?”
- Pete Holmes (07:45): “It's very unnatural and very strange that I saw you two days ago in Boston.”
- Both emphasize how rare and refreshing their instant rapport felt.
2. Flying, Humanity, and Existential Weirdness
- Steven and Pete riff on the “weirdness” of air travel, seeing it as a metaphor for how humans accept bizarre realities.
- Steven Wright (07:45): "I don't want to go 500 miles an hour anymore. I don't think it's right somehow."
- Pete Holmes (08:27): "We don't belong up there. We're sitting in the sky like Greek gods and it's so calm."
- Steven shares a story about a child refusing to fly, highlighting innate human reluctance to defy nature.
3. Contemplating Infinity, Consciousness, and the Limits of Mind
- The discussion veers philosophical: Why are we okay not knowing about the infinity of space or the miracle of consciousness?
- Steven Wright (13:26): "I don't like thinking about how we're in outer space. It's unsettling… how it can go forever, the infinity. And that's disturbing to me."
- Pete Holmes (15:45): "Is it possible for a knife to cut itself or a light to shine on itself? That's sort of the conundrum…"
- Steven compares our grasp of the universe to a three-year-old with a camera: some things may be forever beyond human comprehension.
4. Joke Construction and the Art of Noticing
- Pete probes Steven on his legendary joke-writing: Are jokes a way to process the world's chaos? Is there satisfaction in distilling big ideas into small bits?
- Steven Wright (18:21): "The jokes… I don't think it's helping deal with the world. It's noticing. All art… you're just noticing things and then you're pointing out what you notice."
- On joke structure: Steven credits Woody Allen and George Carlin as primary influences on his precision and style.
- Steven Wright, on Woody Allen (19:22): “He had a joke… in the story, he said: then the woman became a street walker in Venice and she drowned. He's my hero of comedy.”
5. Economy and Musicality of Comedy
- Pete and Steven analyze the value of brevity and rhythm in standup.
- Steven Wright (24:28): "How can you get the point across with the fewest amount of words… also they'll get to the laugh quicker. No waste. No wasted words."
- Pete Holmes, illustrating (26:00): "I bought a paper shredder. It came with a manual. So that was the first to go."
- The act of paring down words is likened to bonsai trimming or writing haikus.
6. Process, Instinct, and Audience Uncertainty
- Both reflect on the unpredictable magic of whether a joke works.
- Steven Wright (33:29; 40:36): "Never… I never knew which ones. Still don't know… My opinion is meaningless of what it's going to be because you can't tell."
- On joke “tryouts”: “If it doesn't work three times, I throw it away. If it works three times, then I think I can count on it.”
- Pete shares how sometimes a niche joke will only make sense in a certain crowd or with enough context (e.g., a recorded special).
7. Philosophy of Performance — Danger and Delight
- Steven compares performing an hour set to running across a lake of thin ice, always hoping not to fall through.
- Steven Wright (44:12): “I see this, I see like an 80 minute show… You're running across a lake of thin ice. It's breaking behind you until the other side.”
- On bombing: “I just think those… they didn't like those jokes. I feel bad that they didn’t like them, but I don’t feel, like, negative about me as a person.”
- Pete contrasts this with a more personal sense of exposure: “I feel rejected. If you’re a comedian like me… If that doesn't happen, it can be very painful.”
8. Comedy as Service vs. Self-Expression
- Pete questions if Steven views his art as a service to others.
- Steven Wright (48:12): “I'm just trying to write things that they… I hope they laugh at… The fact that they get so much joy out of it is almost like… That's after the fact. Sounds kinda cold, actually. I'm just trying to make them laugh.”
- On joy in success: "When a show goes great, I do feel… like I ran across the lake and I got to the other side and wow, that went… And it's over now. It's over.”
9. Creative Routine, Subconscious, and Influences
- Steven describes his creative rhythm: daily biking, coffee, and letting ideas marinate until the subconscious delivers them with clarity.
- Steven Wright (58:32): “…I love to ride a bike every morning… I'm addicted to it for, like, 33 years."
- On the subconscious, batteries, and his favorite joke:
- Steven Wright (54:23): "Your subconscious, to me, is like a factory that's working… a trap door opens… and you think it's out of the blue, but there is no out of the blue. It's because you were working on it without knowing it."
- Shares his favorite joke:
- Steven Wright (52:41): "I went to my grandfather's wake and I was kneeling down at the casket and I started thinking about the batteries in my flashlight… maybe he's not dead, maybe he's just in the wrong way."
10. Boston Comedy Scene and Community
- The conversation turns nostalgic as they reminisce about the simplicity and purity of starting out in the Boston scene.
- Steven Wright (60:47): "It was like being on an island. There was no show business. There was just pure trying to want to do this, figuring it out."
- Steven names peers (Tony V, Kenny Rogerson, Mike Donovan, Steve Sweeney, Don Gavin) and later comics he admires (Bill Burr, Hannibal Buress, Jim Gaffigan).
11. Connection, Intensity, and Artistic Symbiosis
- The episode closes with mutual appreciation for each other's intensity and connection, and a meta-conversation about the unlikelihood of their quick rapport.
- Steven Wright (70:04): “When I left, I was like thinking how intense you are… you're so intense that my intensity came out.”
- Both delight in the almost “weird” cosmic luck of their meeting.
Notable Quotes & Memorable Moments
-
On human logic:
Steven Wright (09:37):
“A friend of mine… told me she was in Central Park and there was a guy walking with his little boy… The boy pointed up to the sky. ‘I'm not going up there.’ …That is the real logic.” -
On joke writing as a survival mechanism:
Steven Wright (23:47):
“The public speaking was easier to deal with because they were laughing.” -
On the unknowable:
Steven Wright (13:51):
“A human being… grows on its own by itself… but I think our minds will never know… as far as the universe operating, we’re like that three-year-old [with a camera]. We are. Even if 30 million years go by, I don't think the brain will develop enough to go, Oh, yes, now I understand how infinity…” -
On creative process:
Steven Wright (54:23):
“Your subconscious, to me, is like a factory that’s working and you don’t even know that it’s working… information, information, and then your subconscious… a trap door opens from your subconscious to your conscious and it opens and a guy [says], This just in…” -
On Boston’s innocence:
Steven Wright (62:23):
“Just the simplicity and the innocence going in the club… You're going on instincts. Just very innocent.” -
On returning home after achievement:
Steven Wright (74:16):
“If I had been Neil Armstrong and… I went to visit home… my mother would say, you were just on the moon. Wipe your feet. That's it.”
Important Timestamps
- Serendipitous Meeting & Airplane Weirdness:
[07:02]–[12:22] - Infinity/Space & Consciousness Discussion:
[13:26]–[17:57] - Joke Writing/Economy:
[18:21]–[26:35] - On Trusting Audience, Joke Testing:
[33:29]–[41:43] - Philosophy of Performing, Surviving the “Lake of Thin Ice”:
[44:12]–[46:46] - Steven’s Favorite Joke (“Grandfather’s Wake”):
[52:41]–[57:46] - Boston Scene & Comedian Community:
[60:10]–[65:44] - Intensity & Connection:
[70:04]–[71:12] - Meta Ending – “Keep it Crispy”:
[76:08]–[77:05]
Conclusion
This episode is an uncommonly revealing, funny, and philosophical exchange between two master comedians. Steven Wright shares the roots and mysteries of his minimalist style, credits his comedic lineage, and humbly admits to the perpetual unpredictability of making people laugh. Pete Holmes matches with earnestness and vulnerability, sparking reflections on the art, service, and risk of comedy. Listeners witness not only the craft but also the shared weirdness and wonder that comedians carry offstage—two minds, vibing hard, painting pictures in each other's heads.
Final words by Steven Wright:
"Keep it crispy." [77:00]