How Improv Makes You Better at Being Human with Annie & Levin O’Connor
Some of the most important things improv has taught me have very little to do with being funny.
That’s one of the reasons I’ve wanted Annie and Levin O’Connor on this podcast for a long time.
They’re the owners of Last Best Comedy Club here in Bozeman, Montana, and between the two of them they have more than 50 years of improv experience. They’ve performed, taught, built comedy communities, and somehow remained married through all of it, which may be their most impressive accomplishment.
Last Best is also really personal to me.
When Kelly and I moved to Montana, it was during COVID. We didn’t know anybody. Then our house caught on fire and we had to move out for eight months.
Not exactly the smoothest introduction to a new town.
Around that same time, Last Best Comedy was starting to grow. I reached out, took classes, eventually joined shows, started teaching improv there, and made a whole group of friends.
It became one of the places where Bozeman actually started feeling like home.
So when I sat down with Annie and Levin, I wanted to talk about more than comedy.
I wanted to know what spending decades improvising with other people had taught them about life.
You Get Better at Failing by Failing
One of the first things we talked about was failure.
Improv is basically repeated exposure therapy for screwing up in public.
You try something. Sometimes it works. Sometimes it doesn’t. Then the scene keeps going.
Levin described improv as a kind of microcosm where you get to practice being the person you want to be in everyday life. You take risks, experience failure, survive it, and eventually develop a little bit of a callus to that uncomfortable feeling.
And once failure stops feeling so catastrophic, you’re willing to take bigger risks.
That applies pretty far beyond comedy.
A lot of us spend an incredible amount of energy trying to make sure we have the right answer before we speak, the perfect plan before we start, or enough confidence before we try.
Improv doesn’t really give you that option.
You have to go.
And then you figure it out together.
You Don’t Need the Perfect Idea
I loved something Levin said about not waiting around for a “good idea.”
In improv, you don’t necessarily need to walk into the scene with something brilliant.
You offer something.
Then the other person hears it, adds something, you respond to that, and together you can turn what looked like a mediocre idea into something great.
That requires trust.
It’s the whole “I’ve got your back” mentality. And I think that's one reason collaboration can be so powerful outside of improv too. Sometimes perfectionism convinces us that we're supposed to have the entire thing figured out before we let anyone see it.
But maybe the better approach is:
Start with something. Let somebody else make it better. Then make their thing better.
Repeat until you’ve built something none of you could have created alone.
Say What’s Actually Happening
Later, we got into something I’m still working on as a stand-up comedian: what to do when the room feels weird.
Maybe a joke isn’t landing.
Maybe the audience has strange energy.
Maybe something is happening right in front of you that isn’t part of the plan.
My tendency is still sometimes to think, Okay, ignore it. Get back to the material.
Improvisers are trained to do almost the opposite.
Notice it.
Say it.
Be in the room you’re actually in.
Annie talked about making direct eye contact with an audience member and simply asking something like, “Are you having a bad time?” Suddenly you’re not a performer desperately trying to force people to laugh. You’re a human being acknowledging what everybody can already feel.
And strangely, that vulnerability can get people back on your side.
That idea works offstage too.
How many conversations get weird because everybody knows something just happened…and nobody wants to say it?
Someone makes a strange comment. The energy changes. Everyone politely moves around it.
Usually the relief comes when somebody finally asks:
“Wait. What was that?”
One of my favorite lines from this conversation came from a friend of theirs:
“Your life is usually as good as as many uncomfortable conversations as you’re willing to have.”
That’s annoyingly good advice.
The Good Old Days Are Happening Right Now
Then the conversation went somewhere I didn’t really expect.
Improv disappears.
You can have an incredible show. The room explodes. Everyone walks out buzzing.
And the next day, you can barely explain why it was funny.
There’s no finished painting to hang on the wall. No album. No book. Even if you record the show, watching it later doesn’t really capture what happened in that room.
Levin talked about there being some sadness in spending decades making art that disappears almost immediately.
But that’s also what makes it beautiful.
A coach once told their team before a show to stop and appreciate that exact moment because someday it would end and it would never exist in exactly that form again.
That hit me.
Because recently, some friends and I were standing around after a show at Last Best, everybody laughing and hanging out, and we basically said: These are the good old days right now.
Not someday.
Right now.
That might be one of the biggest lessons improv can teach us.
You don’t get to keep everything.
Sometimes all you get is the experience of being there.
So be there.
Comedy Is Really About Belonging
Toward the end, I asked Annie and Levin whether they realize they’ve essentially built a life around comedy.
Their answer surprised me a little.
Comedy isn’t really the ultimate goal.
Community is.
They want people to have somewhere to go. Somewhere to make friends. Somewhere the misfits, outsiders, or people who haven’t quite found their people can walk in and feel like they belong.
The laughter is what brings everyone together.
But underneath it is connection.
And I think that’s a big reason Last Best has meant so much to me personally.
I showed up in Montana during a pretty lonely and chaotic time.
Then I found a room full of weird people willing to make stuff up together.
Turns out that was exactly what I needed.
What Are You Saying Yes To?
We ended by talking about one of the most famous ideas in improv: Yes, and.
So I asked Annie and Levin what they’re trying to say yes to now.
Annie talked about choosing strength and longevity for her body instead of chasing an old idea of what her body is “supposed” to look like.
Levin talked about being more intentional about the things he gives his time to—because every yes is potentially a no to something else.
Then they turned the question back on me.
And my answer was: Being a comedian.
I started stand-up years ago, quit, came back, built a career speaking about humor, and for a long time I’ve been more comfortable describing myself as “a speaker who talks about humor.”
But I don’t think that’s the direction I want anymore.
I want to do stand-up.
I want to do improv.
I want to keep studying comedy and getting better at it.
I want to be able to say:
I’m a comedian who also speaks about humor.
Maybe that sounds like a small wording change.
It doesn’t feel small to me.
So maybe the question for all of us is the same one we ended with:
What are you ready to say yes to?
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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?
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