(My final performance in Pittsburgh,

The Robert Isenberg See-You-Soon Tour,

plays tomorrow night, July 20, 8 & 10 p.m.,

at The Arcade Comedy Theater, Downtown. Join us!).

I still remember telling my first joke.

I was riding in the car with my Dad. I was in elementary school. The Green Mountains scrolled by the window, along with the rolling fields and hills of my hometown. My heart pattered, bird-like, because I was pretty sure this joke would work.

“Hey, Dad,” I said. “What does Darth Vader say in his sleep?”

“What’s that?” Dad said.

Then I made that iconic breathing sound—the krkrkrkrkrkr-khwoooo that Darth Vader always makes through his mask, but also slightly nasal, like a snore.

My Dad laughed. And not just a chuckle or a snort, but a triumphant bellow.

“Now that,” he said, “was a joke.”

Until that moment, I hadn’t really understood how jokes operated. Their mechanics defied me. I would use the basic structure of a joke, like: Hey, Dad, what is the color of a leaf? Green!” Then he’d shake his head and say, “That’s not a joke, though. It’s a statement, but it’s not funny.”

I was determined to be able to make people laugh. But I didn’t really know anything, and I certainly didn’t grasp irony. The comic genius of my grade school was MacArthur Stine, who was effortlessly funny and never laughed at his own punch lines. He had an encyclopedic knowledge of pop culture. Like all class clowns, he was whip-smart and could get away with anything, because the teacher always secretly loved him.

Not surprisingly, MacArthur Stine grew up to be a pro sketch comic.

 •

This is all to say that comedy isn’t my natural habitat. Some people are born with the comic spirit, but not me. At birth, I was literal and straightforward, sensitive and ponderous. I loved humor, but my understanding was cartoonish—mostly because I watched only cartoons. I could execute bone-breaking slapstick, to the horror of adults, like slamming into walls, tripping and rolling, and dead-falling to the ground. But there’s only so much clumsiness someone can watch. People like wit and irony. They want a good zinger.

The older you get, the more weathered and cynical, and like a bolt of lightning, humor electrified me in seventh grade. I owe a lot of this to Aaron, my adolescent best friend and one of the most brilliant and iconoclastic people I’ve ever met. He showed me Mad Magazine. He played Naked Gun 2½ on VHS. We wrote short comic sketches for class assignments. Aaron could be quite serious, but he also loved to improvise with his environment; to Aaron, the world was a tactile, interactive place, and he could toy with it at will. Being shy would never win me friends or fulfill me as a living, breathing human, I realized. It wasn’t enough to be a weird little ginger who thanked people too much. Something had to give.

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Understand, though, that Vermont is a kind of bubble. I had no cable or Internet growing up. My parents’ on only periodicals were National Geographic and TIME. Vermonters famously avoid the problems of “Flatlanders,” and when they rant, it’s to people who already agree with them. The only Vermont comics I know are Tom  Murphy and The Logger, who are downright wholesome.

The elephant in the room: Vermonters offend very easily. People don’t move to America’s most rural state because they’re social butterflies. You can silence a room with one ill-advised comment. Luckily, everybody loves Garrison Keillor.

Not surprisingly, my first successful comedy was recorded on audiocassette in my friend Rory’s basement. Rory was also facilely hilarious, a master of voices and witty banter. I wrote a comic script based on an ill-conceived role-playing game, Ars Magica, about a klutzy wizard and his long-suffering henchman. I gave the cassette to my Mom to listen to on her hour-long commute to work. I didn’t expect much. It was just adolescent silliness, after all.

“What did you think?” I asked dully, assuming she’d hated it.

“I loved it,” she said.

“Really?”

“Honestly,” she said, “they’re the best characters you’ve ever written. And the dialogue is wonderful. It’s so funny.”

So there: My Mom liked it. Gold star.

 •

Three centuries after my family arrived in the New World, my family is still fairly Germanic. I love our New England vibe, but we are relentlessly formal. And relentless formality isn’t exactly a recipe for edgy standup.

Don’t get me wrong: Aside from being wonderful, my parents are very good-humored people. They love to laugh and they greatly value cleverness. We like to riff at the dinner table. But my family isn’t funny. We don’t trash-talk each other or play pranks. Our language is generally Rated PG. I prefer it this way, because I love the way I grew up. But funny families always astonish me. Those families seem impervious to insult or sarcasm. They are impossible to fool. They leapfrog from punch line to punch line. They have energy and verve that I couldn’t imagine.

Even when it’s just a big ruse to hide their existential pain, I still find it convincing, because, goddamn it, they’re just so funny.

 •

Joe Lyons and I started the Hodgepodge Society overnight (literally), and our first show was a genre-defying sleeper-hit. Folks just loved the idea of two goofballs in tuxedoes reading scripts on music stands. But I didn’t magically become funny one winter day in 2006. Making people laugh took years of serious practice.

This is typical, of course. Like most people, I used to think that comics just stood on stage and invented their monologues as they went. I could never do that, I thought morosely. Sigh.

When I realized that almost all comedy is scripted, and that improv artists are extremely rare (and rigorously trained), I realized that yes, perhaps I could make people laugh onstage. Theater helped, of course, but I also recognized that “comedy” was not my bag. I could never be a Gaffigan or Hicks. For that matter, I could never be a Rudd or Rogan or Apatow. I need a little entrée with my dessert. I laugh hardest when I’m not expecting to laugh, when I don’t need to laugh. Comedy clubs are the death of me, with their two-drink minimums and aura of misery. Sketch shows get tedious. Unless it’s fantastic, improv makes me chew all the flesh from my thumb.

But “humor” is a different category. Humor is the stuff of Steve Martin and The Far Side cartoons and The Muppet Show. Dave Barry is a humorist. Sarah Vowell is a humorist. It’s not that they’re smarter or more sophisticated or better people or openly laugh at New Yorker panels; it’s just a different temperament. Carlos Mencia must gore his audience like a bull. David Sedaris warms you up, draws you in, and when he reaches his punch line, you’ve forgotten that you’re supposed to laugh. Laughing at comedy means relief. Laughter at humor means joy.

For half a decade, Joe and I entertained audiences as our Hodgepodgean selves, Lord Robert von Isenberg and Sir Joseph Lyons, Esq., and we had mountains of fun. The form felt free-spirited and inoffensive—the tone of an adult “Fraggle Rock.” For nearly 10 years, I have co-written the Pittsburgh Monologue Project with my friend Brad Keller, and while many of these monologues are serious and even grim, scores of them are sidesplitting. For a full year, I co-hosted For Real For Real with my friend Gab Bonesso, a Moth-style storytelling series that was routinely hysterical. During our first open mic, a random guy approached the microphone and said: “I wasn’t gonna tell a story tonight, but I guess I’ll tell you guys why my family calls me The Naked Ninja…”

I mean, really. You can’t make that shit up.

 •

The Robert Isenberg See-You-Soon Tour is a rare opportunity to revisit my comic incarnations. To work with such close friends—and such talented comic actors—is a dream come true, a luxury I will not enjoy again for a long time. If laughter is the best medicine, then tomorrow’s show will serve as a kind of late-night pharmacy. I’ve come a long way since the Darth Vader routine. When I bow out of town, the last thing I want to give people is an irreversible smile.