Comedian James Gregory

Comedian James Gregory will perform Jan. 19 at High Point Theatre in High Point.

In more ways than a few, James Gregory is not your typical comedian. He was not the class clown in high school, did not grow up planning to go into the entertainment business, did not start his comedic career right out of college.

His material is G-rated, and if he veers into the political realm at all, it is in a nonoffensive way. He doesn’t bombard the audience with one-liners but is more of a storyteller. He has never been a TV or movie star, preferring radio appearances on both syndicated (John Boy and Billy, Rick and Bubba and others) and local shows.

All he is is “the Funniest Man in America.” And even that has a caveat. (More on that later.)

The Georgia native, now living in Woodstock, Ga., found his way into comedy purely by accident. A salesman by profession (who also worked stints with the U.S. Postal Service and Defense Department), he and his buddies used to frequent The Punchline in Atlanta, which in 1982 became the first stand-up comedy club in the Southeast. One Tuesday night — which was open mic night — his pals talked Gregory into getting onstage.

He tried it again the next week and, oddly to him, became an instant hit. A month or so later, the club asked him to become the regular emcee, and, voila, a career was born.

“Not in my wildest dreams did I ever think of getting in the entertainment business,” he said. “I’d never given it a single thought. Then it became something to do for fun, but in a matter of months, I realized that possibly I could make money doing it.”

The early- and mid-’80s was the era of the comedy club boom, with hundreds of clubs springing up nationwide, seemingly overnight. And Gregory broke in at just the right time to ride that wave until it crested.

“By early-’83 a club opened in Columbia (S.C.), then Greenville (S.C.), then Augusta (Ga.), and I was not only working all over the Southeast, soon it got to be nationwide. I would drive to Oklahoma, work six nights a week and make $400.”

His career got a major shot in the arm, again purely by accident, in 1986, when a columnist for the Huntsville (Ala.) Times, Billy Joe Cooley, happened into one of his shows. In his column a couple of days later, Cooley wrote of Gregory, “In my opinion, he’s got to be the funniest man in America.” Naturally, Gregory put the quote in his promo kit, and before a show in St. Louis a few weeks later, it showed up in the St. Louis Post-Dispatch.

“I got to thinking, ‘I may have found something here,’ ” said Gregory, laughing. “They had said it — I didn’t say it — so I decided I’d try to use it as a marketing tool.”

It must have worked because 30 years later, he’s still using it.

By the mid-’90s, the comedy club phenomenon had worn off, and many comedians fell by the wayside. But the tenacious Gregory didn’t just survive, he prospered because of a few changes he made to his act and his business model.

Rather than waiting for the phone to ring, he went out and began booking himself into theaters, clubs and special events. He rented the venue, did his own publicity and marketing, named the ticket price, and kept everything over expenses. Plus, he discovered that there was a huge market for corporate and society gigs — they paid well — and he became (and still is) a regular on the toastmaster, banquet and corporate-party circuit.

He also cleaned up his routine, explaining his reasoning thusly: “When you’re doing clubs that sell liquor, it’s all adults, and pretty much anything goes. But when I started doing theaters, obviously kids 9 to 13 can come, so it just makes good sense to keep it clean. Say Mr. and Mrs. Jones come and buy two tickets, but if they bring their two kids, you’ve sold four tickets. You’ve doubled your audience. Basically, it was just a sound business decision.”

So when James Gregory brings his knee-slapping, front-porch humor into the High Point Theatre on Jan. 16, feel free to bring the kiddies and whomever else loves to laugh.

He’s still, after all, the funniest man in America.

Contact Ogi Overman at

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