You, Me, Them, Everybody host Brandon Wetherbee has had some really good—and really bad—shows over the course of his podcast’s five-year run.

The good shows, says the 31-year-old, led him to meet new friends, explore new cities, and snag great jobs (including a stint writing about comedy for Washington City Paper). He’s interviewed musicians, comedians, writers, and competitive eaters. He’s packed houses in Los Angeles, New York City, Chicago, and D.C.

And the bad shows? “I booked a man because he wrote a very cool horror book that I liked. About an hour before the show, I realize, that’s the guy that edits Mr. Skin, the nudie site.”

Another time, one of the comedians he booked—one he can’t mention by name anymore—got sort of militant onstage. “He essentially had a meltdown,” recalls Wetherbee. “He was bombing because he was a horrible comic. He’s doing, like, really shitty ’80s hack humor, and then he threatened to fight someone’s dad in their 60s.”

Wetherbee, who daylights as the managing editor of Brightest Young Things, could go on forever about what he’s learned on the show, partially because he’s learned a lot, and partially because he really likes to talk about his labor of love.

At the upcoming five-year anniversary show on Dec. 3 at Wonderland, Wetherbee will reunite with old friends like comedian Jenn Tisdale and Wetherbee’s favorite musician, Daniel Knox. The show will also include pre-performance trivia by comedian Natalie McGill, an interview with Church Night’s Linsay Deming, a semi-humorous discussion on race with Haywood Turnipseed Jr., a set from Furniteur, and a full house band, Typefighter. “This is the best show in terms of music,” says Wetherbee.

The origin of You, Me, Them, Everybody’s live show is well documented. It started in 2009 at the Hungry Brain in Chicago. Wetherbee bills himself as a late-night version of Terry Gross or Studs Terkel, and on stage, he weaves interviews with local notable people, comedy, and music into a show performed live and recorded for download on iTunes. Throughout the year, the show travels across the country, most often to Chicago and New York City. Wetherbee also hosts occasional performances in Los Angeles, Philadelphia, and Baltimore.

Wetherbee says he’s grateful for the experiences he’s had, but he’s become a little jaded, too.

“If there’s anything I learned, it’s that it really isn’t any different than a band touring,” says Wetherbee. “That’s good and bad. You get to meet really cool like-minded individuals. … [but] it’s fucking boring. You realize that you’re traveling on a bus or a train or a plane for a very long time and usually not for a lot of money. At best I will break even. And I’ve just not been with the person I love for two or three days,” he says, then adds, “and I’m sleeping on a couch and I’m in my 30s.”

That’s not to say that Wetherbee doesn’t love what he does. In fact, he says quitting is the furthest thing from his mind, despite the short list of grievances. “I love it,” he says. “The problems with it are very garden-variety and come with anything in the creative arts.”

When the show started, Wetherbee aimed for a polished, standardized product. He’d book influential guests, schedule weekly shows, and market his show as much as possible. Nowadays, the show is looser, rougher around the edges, more malleable. Many of his guests are old friends. There’s no marketing, just word of mouth. It’s safe, it’s comfy, and it’s what Wetherbee wants right now. “I just like to fuck around with the format now. It’s a lot more fun,” he says.

Moving forward, Wetherbee’s goal is to focus his creative energy on eight annual pre-recorded shows for download. “I want to do less live shows and more one-on-one because I really enjoy that,” he explains. “And it takes more brain effort.” There would still be live shows, he explains, they just won’t be the focal point like they are now. “Doing this for so long, I’m like, what’s worth it? What’s going to be the most fun?”

But Wetherbee isn’t burned out. When asked how long he expects You, Me, Them, Everybody to last, he doesn’t hem or haw.

“I think I’ll do the talk show or something like it, the podcast, indefinitely,” he says. “Just maybe not live.”

Top photo by Franz Mahr