The artist is a paradox. One side is cultivated—the technique that takes a lifetime of discipline, patience and order. The other side is wild, with the inborn singular perspective that sees the world differently. The painter lives in our city, but sees it in shadows and light. The musician walks down our street, yet hears not jackhammers and sirens, but rather snares and Stratocasters. The comic mines mirth from the mundane.

George Carlin knew this, and often answered the tired question, “What would you be if not a comic?” immediately: “A trial lawyer. Same job!” The confused interviewers moved on, and that’s a shame, because Carlin was trying to explain the paradox—the puzzler’s brain inside a man who can solve the puzzle for the rest of us. The setup is the opening statement, the punchline the final argument, the laugh the verdict.

Brian Regan is such a litigator. He offers a dubious premise (ironing boards are hilarious), presents the evidence with words and cadences he’s refined over a thousand performances (every ironing board on the planet opens like a witch being boiled in oil), plays on our sympathy a little (he imagines a hapless inventor trying to get the “surfboard-shaped device supported on two thin crisscrossing poles balancing a metal object filled with water the temperature of lava” past a skeptical safety board) and in the “ladies and gentleman, do justice” final argument, lands the joke by contrasting raw physical comedy (opening the ironing board) with a quote from Macbeth (shrieking “double, double, toil and trouble”).

The verdict? It kills every time.

“I love the craft. I love moving words around, changing an adjective,” says Regan. “A joke I started in January is different in December. It’s a piece of clay that I’m turning into a vase.”

Comedy is born from tragedy, we’re told; therefore, a comic is driven by pathos. But Regan is a paradox here, too. The former college football player was raised in Miami in a big—he’s one of eight siblings—happy Catholic family where jokes told at the dinner table were currency. “Unless you get people laughing, nobody’s passing any fish sticks down your way,” he says. “I exist!”

But his early hits were accidental. When Dad pulled the family station wagon over to allow a funeral procession to pass, Regan asked, “Have you ever seen a real, live dead man?” As the mourners filed past, his dad guffawed. The son was intrigued.

The clouds parted in his college speech class, where the week’s assignment was “sell a product.” Regan’s “product” was a mystery item concealed in a rumpled brown paper bag. The class perked up. His deadpan pitch: “Are you ugly? Do people cross the street when they see your face? Then you need (carefully removes the item from the bag and casts it aside) The Paper Bag!” The class howled at the bait-and-switch. The matronly instructor chortled. He remembers walking back to his dorm, electrified: “What was that?”

That, of course, was the lightning strike, evidence that he saw the world differently. If he could harness it, this could be a job. So, he went to work. He presented himself at The Comic Strip, where he flipped burgers and auditioned. On his fifth try, the club owner let him go on at the end of the night as the headliners were wrapping and the audience shuffling out.

The funnier he got, the more they stayed. Could he go on every night? No comic had ever asked before, but sure, kid. He’d put the burgers on, turn the burner down, take the apron off, do five minutes onstage, put the apron back on—the burgers were done. “They didn’t even know they were looking at the cook,” he says with a laugh. At closing time, perplexed patrons glimpsed the embarrassed stage talent dumping the kitchen trash out back.

He got better, and then he got great. Comedy clubs with cracked vinyl booths became theaters with velvet chairs, stuffed with devoted fans won solely on the strength of his stand-up. Now, Jerry Seinfeld calls Regan his favorite comedian, while Chris Rock once said, “No comedian in the world says, ‘Yeah, I want to follow Brian Regan.’”

Nonetheless, he’s still taking risks, relentlessly sculpting. When critics praised his physical comedy, he switched to a narrative style. Audiences relaxed into his dad jokes, but now he’s on Palestine and gun control. “I like when you can’t predict what I’m going to do,” he says. “Like music, comedy is ever-evolving.”

He promised me 20 minutes and gave me 45. He laughed at my jokes, patiently allowed my tortured courtroom analogies and quipped, “Thanks for saying I’m smart. Most people compare me to a clown.” I’m telling you: Kills every time.