Nick Kessler

Nick Kessler

Courtesy of WGNA

Country artists are routinely interviewed while visiting radio stations and have become accustomed to a certain level of professionalism during those on-air chats with personalities. So imagine the stars’ surprise when they find themselves being grilled on camera by a sweaty, awkward and palpably uncomfortable man who reads a series of insipid questions to them from a legal pad or an elementary school composition book, then vigorously nods or gapes at them bug-eyed while they try to answer.

That’s exactly the scenario country artists face when they happen into WGNA Albany, N.Y.’s Worst Interview Ever series, a bit that completely lives up to its name. The funny series is the brainchild of Nick Kessler, the promotions manager for Townsquare Media’s Albany cluster who also hosts a Sunday afternoon show on WGNA. He enlisted the help of the cluster’s digital managing editor Ariana Sheehan, who shoots and edits the clips, then promotes them on social media.

Kessler originally hoped someone else at the station would pick up his idea and run with it, but when nobody seemed willing to play the role of the buffoon, he took it on himself, conducting the first interview in May. So far, he has pranked eight country stars and is now expanding the concept to WGNA’s sister stations in other formats, beginning with an interview with John Cooper of Christian rock band Skillet for rock station Q103.

Kessler and Sheehan say the artists and their teams are never in on the joke, and it takes them varying amounts of time to catch on. The artists are only told Kessler is new to interviewing. Consequently, the conversations produce some classic reactions, like when the Eli Young Band’s Mike Eli gave Kessler some serious side-eye or when American Idol winner Trent Harmon all but rolled his eyes and looked like he wanted to crawl into a dusty potted plant purposely placed so close it was touching him. Kessler says during their interview, and for about 10 minutes afterward, Harmon “thought the radio station let a special-needs person win a contest to interview him. That’s why he was going with everything I said. He didn’t want to shoot anything down.” Adds Sheehan, “And that’s exactly what we want.”

Each WGNA video provides countless squirm-inducing moments, much like WSIX Nashville afternoon hosts Tige and Daniel’s hilarious and long-running Tiny Couch interview series, in which they squeeze themselves onto either side of a star perched on a love seat and lob stupid questions. (Watch Tiny Couch segments with Maren Morris  and Eric Paslay here and here.) Kessler insists on calling Dustin Lynch “Dusty” during their chat and repeatedly refers to Mike Eli as “Eli Young” or just “Eli.” (Watch all of his interviews here.

During an interview with Justin Moore, Kessler paused to check his phone, then explained that when an alarm on his device goes off, his therapist told him he’s supposed to look in a mirror and compliment himself. He immediately produced a hand mirror and proceeded to do just that. When he asked the singer if he ever gets nervous, Moore shot back, “No, but clearly you do.”

While interviewing Eli in the backseat of a car, Kessler poked at the large “highways and broken hearts” tattoo on the singer’s arm, then asked him, “Does that mean anything to you?” Another straight-faced question he had for Eli: “Do you think the back of your knees should be called ‘knee pits?’ ”

Kessler began an interview with Kip Moore by thrusting his hands toward the singer and asking if they smelled like gasoline. During a chat with Toby Keith, Kessler pretended to confuse the singer's restaurant chain with one owned by Jimmy Buffett, and later asked Keith to autograph a birth certificate for his teddy bear.

In the middle of a chat with Harmon, Kessler paused at length to jot down notes on his legal pad. He also sang to Harmon and asked the Idol star to critique him, then followed up by asking if he was related to actor Mark Harmon.

The artists’ reactions are priceless. “They have no idea what’s going on,” says Kessler, who notes that Justin Moore’s bodyguard “was about to break me in half.”

Kessler admits his goal is to make things “as weird as possible” and produce comedy gold in the process. He’ll drop a water bottle or do whatever it takes to “create chaos,” according to Sheehan. Even when the artists do catch on, Kessler says they still don’t know what questions are coming, so that keeps them off guard. “I try to throw some curve balls in there,” he says.

Says Sheehan, “My favorite part is when Nick starts touching his forehead and looking really upset that it’s not going well, because you can tell the artists actually feel for him.”

Sheehan and Kessler have discovered they need to kick other staffers out of the room when they conduct these train wreck interviews so they don’t give the joke away by laughing. But even Sheehan says she has a hard time playing it straight and often finds herself looking down at the floor to keep from losing it.

“I just sit there straight-faced with a camera and seem encouraging of his dumbness,” she says. “I have a really hard time, and by the end I just crack. But by the end, they usually understand the joke.”

Adds Kessler, “They either pick it up within 30 seconds or they will go the whole time not knowing.” And while he does actually prep for the interviews, he has found that the less he knows about the stars, the more ridiculous his questions can be.

Kessler promises future interviews are going to get “way more awkward and crazy.” And while he knows media attention about his series might ultimately spoil the element of surprise, he hopes artists will recognize that he’s making a fool of himself rather than them and they’ll still want to play along.

This article first appeared in Billboard's Country Update -- sign up here.