Saying Goodbye to “The Funniest Man in America”
6 min readJun 11, 2024
I first saw and met James Gregory in the early 1980s. A new comedy club, the Punchline, had opened in Atlanta. James started with a spot in open mic night but quickly became a crowd favorite and headliner. My friends and I regularly traveled to Copeland Road for his shows. He often stretched it out to a couple of hours, sometimes longer, trying out new material. It was clear he loved what he was doing.
As Southerners, we get our fill of others making fun of us and our quirks and eccentricities, but done the right way and coming from one of our own, we enjoy a hearty laugh at ourselves. James Gregory not only could get away with making fun of the very people in his audience, but he had them coming back time and again for more. This was the essence of “The Funniest Man in America.”
Over the forty-plus years that I regularly visited James’s shows, I found myself divided between wanting to hear his old, familiar classic material and laughing profusely at the new stuff; I realized he would have to do an all-night show to get in everything I wanted to hear. He was like a band with dozens of great hits that only had room for 12 in the setlist.
There was so much more to James than many knew. One of his trademarks was making fun of his own fear of flying. He always said that he flew once a year so he could catch up on his drinking and praying. He also expressed frustration at the flight attendant’s narrative about waterborne landings, observing that there were no oceans between Atlanta and Little Rock, but there were plenty of mountains, which didn’t get discussed.
The truth is that, despite his fear, James would fly to the Middle East to entertain a very special audience: our troops. You won’t find those pics on his Facebook page, and you won’t see them mentioned in interviews. It was never done for credit or publicity but for respect of those who serve. Of doing three shows a day on battleships and aircraft carriers, James says. “This was the most emotional experience of my entire career.”
I’ve interviewed James for stories a few times over the years and shared a few meals together. I am sad that those times are no more.
The story below is from 2021. It is reprinted as it was, not updated to reflect his passing.
The article…..
When you are known as “The Funniest Man in America,” like comedian James Gregory, the bar is set pretty high every time you step on stage. With more than 8,000 live shows under his belt and numerous appearances on some of the country’s most popular TV and radio shows, like Bob and Tom or John Boy and Billy, his massive tribe of fans will tell you that he hits that mark every time.
Gregory is a native of Lithonia, Georgia, and began his comedy career in 1982, introducing acts at the Punch Line club in Atlanta, one of the first comedy clubs outside of New York and L.A. Eventually, he was asked to perform his own routines there, and crowds fell in love with his homespun brand of humor. Next, he started taking his show on the road. Gregory performed 8–9 shows each week, touring the country and building a loyal following. He has appeared on stage in 38 states.
In a career that has featured tours with George Jones, Dolly Parton, Kenny Chesney, Reba McIntire, the Judd’s and many more, it would seem challenging to pick a high point. When asked what stands out most to him, James says, “I show up in a place, and it’s sold out, and they’re there to see me; when I hit the stage, that’s the highlight of my life.”
