Mr. Andersson took Dixie on tour in 2008, and with the help of booking and press agents, landed gigs for the next two years. He recalled: ”When the booking company said, ‘It’s looking like we’re not going to book that much more,’ I said, ‘Great. I’m going to take a shot at it.’”

“I thought, ‘This can’t be that hard,’” he added. “Somebody’s a tour booker, a manager, an agent. They’re not born with it. They go to school, they learn. If someone else can do it, I can do it.”

Multitasking is nothing new to Mr. Andersson. In fact, it’s reminiscent of his childhood: He worked his first paper route when he was 8 and consistently held part-time jobs through his adolescence.

Now, at 47, he is co-owner and co-producer of a production company called Down South, which he describes as “the umbrella of all things Dixie.”

What that means is hard work. For nine years, he has cold-called arts centers and performing arts spaces to get bookings. Some cities have been so welcoming that a sequel was called for in 2014: “Dixie’s Never Wear a Tube Top While Riding a Mechanical Bull (And 16 Other Things I Learned While I Was Drinking Last Thursday)” does away with the Tupperware sales and dives into the character’s personal life and philosophies.

“You’d think, 10 years in, that people know the show, it’s easy to get in any market, and it’s not,” he said. “Unless you’re one of the big, big shows, you’re still constantly knocking on doors.”

Drag performances have inched closer to the mainstream since Mr. Andersson introduced Dixie, which cuts both ways. A one-man show with a set that can be packed into a Tupperware bin, “Dixie’s Tupperware Party” isn’t costly to produce, and Mr. Andersson has worked determinedly to establish its name recognition. He knocked on doors in Nashville for four years until “Dixie” was booked there.