Halfway through our interview, comedian Kurt Braunohler says, “I like how you point out I’m really good at failing.” Truth be told, it’s not that he fails more than the rest of us, but whenever he has a big, wild dream, he goes after it and brings his audiences along for the ride. Even in his earliest guerilla theater project, “Chengwin and Chunk,” Braunohler and his friends ambitiously envisioned New York City streets as a landscape for brawls between chicken-penguins and chicken-skunks.

Since then, his sensibilities have brought about more strange and wonderful worlds. He hosted parody game show Bunk on IFC, created a multiformat podcast called The K Ohle and raised money on Kickstarter so a plane could skywrite the message “How do I land?” over L.A.—this phrase became the title for his first stand-up album, released on Kill Rock Stars in 2013. His most recent project is Roustabout, a Comedy Central Studios web series. Its nine episodes follow Brauhonler’s quest to jetski from Chicago to New Orleans in order to raise $50,000 for philanthropic organization Heifer International. (The slogan: “Let’s Get Wet for Goats.”) During his many trials and tribulations along the Mississippi River, he runs into comics Wyatt Cenac, Jon Daly, Kyle Kinane and his long-time comedy partner, Kristen Schaal.

Oh, and in addition to the web series, he’s kicking off The Roustabout Tour in Brooklyn this Wednesday. Braunohler is a friend, too, which is why I felt comfortable asking him about his bad haircuts, the state of his taint and having frozen yogurt atop Mt. Kilimanjaro.

“That’s what life is! You have this idea about what your life is gonna be and then all the little bullshit of life tries to fuck you. We’re all just trying and none of us are doing it right.”

From the beginning of Roustabout—all the river locks, gas problems and sludgy waterways—it’s clear you guys had no idea what it really meant to jetski across the country.
That’s the tension throughout the series: trying to have this big dream live in reality. The show is about a confident idiot who is trying to accomplish something that’s maybe not realistic.

Wouldn’t you say “the confident idiot” is a guise that you wear often and well?
Oh no, that’s just who I am.

What was the low point of the trip?
The most emotionally difficult time was also the most physically difficult time. On the last day, we had to cut across the Gulf of Mexico for 50 miles and we couldn’t stop because we were in the middle of the ocean. It was three hours of just getting tortured by big waves. After that, we were almost to New Orleans and got stopped by a drawbridge [and] didn’t know when it would go up. So it was this physical struggle to get there, and we were almost to New Orleans [where the crew was scheduled to meet Schaal and perform a show] and we just had to sit there. We thought, If we have to wait here for 4 hours, we’re fucked. This could just ruin the whole thing.

It’s interesting how many unpredictable physical limitations made things challenging for you.
That’s what life is! You have this idea about what your life is gonna be and then all the little bullshit of life tries to fuck you. We’re all just trying and none of us are doing it right. None of us. Everyone can relate to that. They might not be jetskiing the Mississippi River for Heifer International but they can understand when things get fucked up because everything always does.

The most important question raised by the series: Will your taint ever recover?
Still swollen, six months later.

There’s some talk about ointment after the first day, but you still had several more days straddling that throbbing patch of leather.
Yeah, we really left out all the rest of the talk about ball maintenance, which is just for the audience’s benefit.

That can be a part of the DVD extra fan “package.” In any case, you don’t really hide how hard some moments of the trip are.
Through the whole show, there’s a triumph but a sadness—which I like. After doing this whole thing, we didn’t raise all the money. We ended up raising $35,000 when the Indiegogo stopped, and we’re hoping to make the whole amount, while people watch the series. But at the time, in New Orleans, we had only made $20,000, which was less than half of what we wanted to.

Remember when you were an adult with a flat top?
What a terrible haircut. I don’t know what I was thinking.

You had it for a long time, you must have felt strongly about it at the time.
I was trying to look not like a banker.

What’s the prank you’re proudest of?
I’m pretty proud of Roustabout. Everyone who was involved was like, “That was one of the most magical times of my life.”

Part of the philosophy of your comedy is about making strangers’ lives a little better by inserting absurdity into them. When and how did this first happen for you?
First, I was raised Catholic. The one thing I like that I took away from it: There’s a hidden world beyond the one we can see everyday. Even with their obsession with saints and holy objects. I was always obsessed with seeing the sacred in the profane—to borrow a noxious term—to see holy things in trash on the street and stuff like that. Then, when we started doing “Chengwin and Chunk,” our idea was to take a very normal, urban space and transform it into something which it’s never been before—in that case, a chicken-skunk fighting arena. People who experience an outdoor area that way won’t just see it on their walk to work, they’ll also remember this experience. That gets mapped on top of that space for them. It’s kind of what inspired me to think about how I could continue to do that but with the comedy I do now.

What ways would you like to grow as a stand-up?
The term “silly” gets applied to me a lot and I think it’s inappropriate. A fart is silly because it’s without thought. What I’m trying to do has a lot of thought behind it. And I am chagrined when I see people are like, Eh, it’s just nonsense. This comes from a very deep place in me, so I want to find a way that it works at a silly level but right underneath, it’s evident that it’s more important.

You have been known to buy greeting cards, write alternate messages inside them and then put them back on the shelf. For a lot of what you do, you must have to just imagine the effects…
Right, and that’s why I don’t like the term “prank” for what I do. A prank depends on a reaction from someone. There’s a moment when the camera turns to someone saying, “What the fuck?” I much prefer things that just exist on their own, and who knows? Maybe I’m wasting my time, and no one ever saw the hundreds of greeting cards I put back. But hopefully some people did. And I think that makes it much more special for them.

Have you ever heard back from anyone?
No, but I’ve been trying. I’m doing this new one where I buy a beer, take a photo of myself drinking it and write them a note with contact info, saying, “I’ll buy you another one.” Then I put these things in the bottle and put the cap on and bring it in [to the store] and put it back in the middle of a six-pack. I’ve done a few of those so far and no one’s contacted me yet, we’ll see. It’s like saying, “Hey, do you want to be friends in the weirdest way possible?”

What’s a project you’ve not been able to accomplish yet?
It would be cool to Segway up Mount Kilimanjaro.

That’s paved?
Apparently, it’s a walking summit. They have a path, and there are off-road Segways. Another thing would be to put a frozen-yogurt soft serve machine right at the top and offer it to people after they’ve been walking for six straight days. This is a joke that works for, like, 8 people a year, but it would totally fuckin’ blow their minds.