23 Sept 2026
35. How Improv Makes You Better at Being Human with Annie & Levin O'Connor
What can improv comedy teach you about failure, trust, relationships, presence, and becoming a better human?
Quite a bit, apparently.
This week on Laugh or Death, I'm sitting down with Annie and Levin O'Connor, owners of Last Best Comedy Club in Bozeman, Montana. Between them, they have more than 50 years of experience performing and teaching improv—and they've also built a comedy community that has become incredibly important in my own life.
We talk about why improv is basically practice for failing without freaking out, why you shouldn't wait around for the perfect idea, and what happens when you learn to trust that the people around you have your back.
We also get into how improv teaches you to read a room, why sometimes the best thing a performer can do is acknowledge that something feels weird, and how those same skills can help with uncomfortable conversations in real life.
Then things get surprisingly existential.
Annie and Levin explain what it's like to spend decades creating an art form that disappears as soon as the show ends—and why that impermanence can actually teach you to appreciate the moment you're in.
Or, as we realize during the conversation:
These are the good old days right now.
We also talk about why Last Best isn't ultimately just about comedy. It's about creating a place where people can make friends, take risks, be themselves, and belong.
In this episode:
What improv teaches you about failure
Why you shouldn't wait for the perfect idea
How "I've got your back" changes collaboration
Why Paul returned to improv
Can improv make you a better spouse, friend, or parent?
How improv builds empathy and awareness
Why comedians need to commit to the bit
What to do when you lose an audience
Why saying the awkward thing out loud often helps
Improv and uncomfortable conversations
Why the best improv disappears
Learning to recognize the "good old days" while you're in them
Why live, human comedy still matters
Comedy as a tool for community and belonging
What Annie, Levin, and Paul are saying "yes" to next
Why Paul is finally saying yes to being a comedian
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Life is hard. We should laugh harder.
Links:
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To learn more about Paul's work, book him for speaking engagements, or explore the science behind humor and resilience, visit: 👉 https://www.paulosincup.com You can also dive deeper into the tools discussed in this episode in Paul's book: 👉 The Humor Habit
All Links For Paul: https://stan.store/PaulOsincup
Episode Minute-By-Minute:
00:00 – Meet Annie & Levin O'Connor of Last Best Comedy
05:00 – Why Their Comedy Club Has No Drink Minimum
06:00 – What Improv Teaches You About Failure
07:00 – Stop Waiting for the Perfect Idea
09:00 – Why Paul Started Doing Improv
12:00 – Does Improv Make You a Better Person… or More Annoying?
14:00 – Anything Can Be Funny If Everyone Plays Along
16:00 – The Empathy Superpower of Improv
20:00 – Your Stage Persona Isn't Your Real Personality
22:00 – Commit to the Bit
25:00 – What to Do When You Lose the Audience
28:00 – Say What's Actually Happening in the Room
30:00 – Why Uncomfortable Conversations Make Life Better
34:00 – The Strange Beauty of an Art Form That Disappears
36:00 – These Are the Good Old Days Right Now
39:00 – The Audience Is Part of the Performance
42:00 – Why Live, Human Comedy Matters
43:00 – Comedy Is Really About Belonging
46:00 – Stop Trying to Force the Funny
47:00 – What Are You Saying Yes To?