By Elle Metz

On a bright stage in a dark room at The Annoyance Theatre in Lakeview, two men, bouncing slightly on their toes, peer into the audience. Seventeen people—mostly young and casually dressed—gaze back. One woman sips a light beer. A goateed man sits up straight in his chair. The two performers, Derek Shoemaker and Blair Britt, ask for a suggestion to start their improvisation.

“Cadaver,” someone calls out. Shoemaker and Britt immediately step back to the middle of the stage, facing each other like sparring partners.

Shoemaker has a round face framed by a dark brown buzz cut and perpetual two-day scruff. Tonight he wears maroon slacks, a short-sleeved, blue-and-white-checked button up and red Vans sneakers—a typical performance uniform for him.

In this first scene, Shoemaker plays a police detective and Britt a medical examiner. They’re trying to solve a difficult murder case. Shifting their weight forward and back, the men discuss the case and gesture toward an imaginary body lying on a morgue table in front of them. Britt rants that he can’t find anything wrong with the body. A knowing look crosses Shoemaker’s face.

“We know about your gift,” Shoemaker says. “We know that you can touch bodies…”

“No, I’m not doing that again, alright,” Britt replies. “I’m not!”

On stage together, the two men’s physical differences are on display. Shoemaker is medium-height with sloping shoulders and dark coloring while Britt is lanky, long-limbed and blond. Their words, like blows exchanged back and forth, pick up speed.

“We need you to do it,” Shoemaker says, matter-of-factly.

“No,” Britt protests.

“You’re the only special-ability medical examiner we’ve got here,” Shoemaker insists. The audience laughs. Buoyed by this, Shoemaker continues. “I need you to touch that body,” he says again and steps forward with authority, his chin jutting out.

“No, I…” Britt begins, his downturned eyes widening uncertainly.

“You gotta take your gloves off and touch that body,” Shoemaker cuts him off, staring at Britt intently.

“No, there’s a very clear procedure,” Britt says.

“To hell with the procedure. We need you to touch that body with your bare hands,” Shoemaker says lowering his voice and emphasizing each word. He points a flattened hand at Britt and the imaginary body. The audience bursts into more laughter. Shoemaker continues, more insistently: “I want you to touch that body, touch that naked body, that naked man. We need you to. We need you to see the visions in your head. Touch the body!”

“You know what it does to me? You know what happens when I touch a body, alright?” Britt fires back and pauses for a moment, deciding just what happens to him. “When I touch a body I relive the last half hour that they lived before they die.”

A man in the back row lets forth a deep, explosive “Ha! Ha!”

“The whole half hour?” Shoemaker says, his voice quivering. A smile flickers across his broad lips and olive green eyes, threatening to morph into a laugh.

“And half the time, it’s real fuckin’ boring,” Britt replies, his voice rising as he stares indignantly at Shoemaker. “The first twenty minutes usually don’t have anything to do with it.”

Shoemaker and Britt continue, jumping from scene to scene down a rabbit hole of improvisation.

They are only two in Chicago’s sea of aspiring comedians. Just between the city’s top training centers, Second City and iO, there are more than a thousand comics. And practically no paying gigs. For every up-and-coming Amy Poehler or Seth Meyers, there are hundreds of performers who won’t make it. Where does their ambition come from? For Shoemaker, the desire to make people laugh was rooted in a fight to escape his own unhappiness.

Seven years ago, he was in a very different place—selling cars in a northern suburb of Chicago. Despite being a good salesman, he hated it. The twelve-hour days, the disingenuous appeals. At only twenty years old, Shoemaker didn’t like the person he was becoming. The only relief from his terrible job was weekly improv classes at Chicago’s legendary Improv Olympic (now iO) comedy school. About a month after starting classes, Shoemaker quit his job to pursue a career as a comedian.

Today, at twenty-seven, he works a temp job as a receptionist at a trading firm so he can take classes and perform at night. So far, Derek has taken dozens of comedy classes, interned at a theater, started his own online comedy magazine“Ca$h Planet” and performed stand-up, sketch comedy and improv. A typical week includes performing a group show at the Playground Theater, writing and directing a short play at The Annoyance and writing a four-episode staged television show.

“Obsessive” is how Shoemaker’s then long-term girlfriend, Laura Hunter, describes him to me. “I think that’s pretty obvious,” she says. They have since broken up.

His theory: the more he does, the better he’ll become and the better his chances of making it. It’s a theory he’s long held.

“In school I was kind of like the class clown, yeah. People either thought I was really funny or super annoying, and it was because I was always trying to make people laugh. Always trying,” he says. “You know that thing of people who don’t say a lot but when they do it’s hilarious? I was the opposite. I said a lot. And I just constantly tried and I still do.”

Constantly trying comes with its ups and downs. The show at The Annoyance was a good one. But not every performance kills. Not every joke works. A few months ago, at the same theater, Shoemaker sat just outside his dressing room, waiting to perform another show. Unlike his boisterous onstage characters, he was quiet, contemplative. The topic of reflection: his depression.

“It’s like you just don’t want to do anything and it’s like a thing that just sucks your motivation and everything out of you,” he says. “It’s so constant. Probably like the past week, I’ve probably had one or two times where I just fell into it.”

In these moments, his line of thinking goes something like this: “I’m not funny, I don’t know what I’m doing. Everything I’m doing is terrible. It’s all bad. I’m writing all these jokes and I’m writing all these pieces and they’re all bad.”

Comedians, as a group, have a dark side. The road to famous funnydom is littered with casualties—Chris Farley, John Belushi, and just last year, Robin Williams. Most recently, “Parks and Recreation” writer Harris Wittels passed away after an apparent heroin overdose. How can people so hilarious be so self-destructive? Of course, comics aren’t alone in their inner turmoil.

Actors, artists, musicians and writers have been self-destructing since long before Van Gogh. The difference is their mode of expression. While musicians may sing about their demons, comedians traffic in laughter. The joy they spread is seemingly the opposite of their depression, making their darkness all the more surprising when it reveals itself.

The contrast between Shoemaker’s funny onstage persona and his moments of despair may not be all that uncommon. In May 2014, the British Journal of Psychiatry published a study detailing how many comedians have a contradictory personality—both manic and depressive—revealing the dichotomy of the hilarious guy onstage and the one who is the prisoner of his own mind.

For the study, more than 500 comedians filled out a questionnaire that measured four psychotic personality traits. The comedians scored significantly higher on all four traits than a control group of people who worked in non-creative jobs. They scored particularly high, though not necessarily to a clinical degree, on two traits—introvertive anhedonia and impulsive non-conformity.

“These two traits are contradictory because one is about introverted, depressive traits and the other is more extroverted, manic,” Gordon Claridge told me when I called him at Oxford University last October. Claridge is a psychologist and one of the authors of the study. “So we interpreted it to mean that the profile is really bipolar, a sort of manic-depressive profile,” he continued. “That was the key to the whole thing.”

When I tell Shoemaker about the study, he isn’t surprised. He sees himself as both introverted and extroverted—although, to see him on stage, you’d never suspect he gets extremely uncomfortable at parties. These opposing personality traits, combined with the fickle nature of comedy, lead to intense emotional ups and downs.

“It almost seems totally pointless really because I’m just doing this for the fleeting moments of feeling like I’m really good at something,” he says. “And then they go away so quickly and my whole life is trying to get that. And every big one that I get is awesome, but you can’t sustain it,” he continues. “It is like a drug, and I have to get better and I have to get funnier.”

On a recent weeknight, Shoemaker banters with another scene partner, his friend Collin Cunninghame. They lounge on Shoemaker’s couch in the apartment he shares with Hunter. It is a small place where the kitchen, dining area and living space all blend into one square room. The walls are white, and the carpet is a murky tan and littered with cat toys. The owner of these toys, an orange tabby named Phineas, watches curiously from his perch on the counter.

Random objects cover two table surfaces, including five Rubik’s cubes. Shoemaker can solve them. A bulletin board hanging near the door displays ticket stubs from famous iO shows and a note from Shoemaker to Hunter: “You’re doing so well, and I’m so proud of you. I love you more than I can describe in words.”

Shoemaker, who once more wears his red Vans, a checkered shirt and jeans, situates himself amongst the cushions with his green marble notebook on his lap—one of several in which he writes sketches. Cunninghame, who is brown-haired and bearded with prominent teeth, sprawls nearly horizontal with his feet propped on the coffee table. The two men brainstorm potential jokes for a show. They recall an idea they had about the cartoon, “Calvin and Hobbes,” and decide to play it out for an imaginary audience. The twist: Calvin is manic-depressive.

“So he’s like: hey Hobbes, how’s it going?” Shoemaker says, sounding cheerful. He sits up slightly and shifts toward Cunninghame.

Cunninghame takes on the role of Hobbes: “Oh hey Calvin!” he replies, in a squeaky voice.

“Do you want to do something?” Shoemaker asks.

“Yeah we can go…” Cunninghame begins, still lying low on the couch, his hands resting on his stomach.

“Ya know what, no,” Shoemaker says, his voice becoming deep and melancholy. He looks away, toward the ground.

“Well, we can go for a wagon ride and shoot T-rexes with laser guns,” Cunninghame says. He giggles and spouts more nonsense suggestions.

Shoemaker pauses, turns back and stares sadly at Cunninghame. “You’re not real,” he proclaims, sounding downcast.

Breaking out of character, they dissolve into high-pitched laughter at the idea that Calvin, a six-year-old cartoon boy, would become depressed. So much so that he recognizes his stuffed tiger, Hobbes, as a fake toy, rather than his best friend. It takes them nearly a minute to recompose themselves enough to keep brainstorming.

Shoemaker, like Calvin, has his moments of disillusionment. He first experienced depression after dropping out of high school during his senior year in Jacksonville, Florida. He would later earn his diploma. Quitting school was a symptom of greater chaos at home. A father with a drinking problem who hit his mother. A mother who eventually snapped, began using drugs and lying about it.

“It was enough to make me like ‘I just want to get out of here,’” he says. “It was making me really depressed. Their relationship was just insane.”

Shoemaker remembers the first time he realized his father was abusive. He and his parents were at home. His parents were arguing. From another room, Shoemaker heard the sound of the blow and his mother screaming. “I don’t know what happened. I don’t know how he hit her. I don’t know if he slapped her. I don’t know what happened,” he says. After that incident though, the abuse continued. “There were a few times when I went in and was just like ‘stop!’ Like yelling at him to stop, ya know. Stop fighting,” he says. “Anyways, that happened a few times.”

On several occasions, his parents’ fights ended in police intervention, and his father was arrested. The situation was “just a big shit storm all at one time,” recalls Shoemaker’s twenty-five-year-old younger brother Pat. It “had me and my brother and my sister all just completely wiped,” he says, “and we all dealt with it in different ways. Derek definitely resorted to the comedy.”

Always a dramatic kid—at just three years old, he would perform “The Derek Show” for his parents—Shoemaker honed his comedy skills during junior high. And then studied drama at his arts magnet high school. When times at home were the worst, he would often escape to a nearby Walmart with his friend and buy comedies on DVD—“The 40-Year-Old Virgin,” the Comedy Central show “Strangers with Candy” and filmed performances of improv group the Upright Citizens Brigade.

Eventually, to get away, Shoemaker moved to Indiana to live with his great uncle and later, to Chicago—the first step on his journey to pursuing comedy full-time.

By turning to humor during this first tough period, he may have set a precedent of using comedy to cope with darkness. “There’s a kind of self-medication aspect,” Gordon Claridge tells me. “Sometimes creativity is a way of dealing with the underlying depression.”

And it turns out humor is pretty effective at tricking a brain in pain—temporarily, at least. “You can’t experience humor and feel a distressing emotion”—anger, anxiety, fear—“at the same time,” Steve Sultanoff told me when I called him at Pepperdine University. Sultanoff is a clinical psychologist and an expert in therapeutic humor. “The experience of humor actually replaces distress with an uplifting emotion.”

Back in Lakeview on a cold Wednesday night, I arrive at Shoemaker’s next improv show—this one performed in a studio office space with a group called Town Hall Citizens. The room is spacious with tan wood floors and exposed brick walls; and the atmosphere is noticeably fancier than other shows. Guests and performers are required to wear nice attire—jackets and ties for gentlemen, dresses for ladies. One of Shoemaker’s group mates, a short, shapely blonde, approaches me and learns that I’m writing a profile of Shoemaker: the comedian. Before I can say anything more, she holds her hand to the side of her mouth and smiles conspiratorially.

“A manic depressive comedian,” she says. She goes on to say that he is a good subject because he’s been at the comedy thing for so long and has experienced so many successes and failures. Also that she loves him and playing with him. And he’ll talk your ear off, she adds.

Shoemaker has been at it for the better part of seven years, a long time for someone his age. During this time, he’s taken classes at The Annoyance Theatre, completed all class levels at iO (twice), been a part of the University of Florida’s improv group, Theater Strike Force, and performed numerous shows.

And yes, Shoemaker will talk your ear off. About anything comedy related. “Saturday Night Live,” for example: “I will go off on people who are like ‘SNL’ hasn’t been funny since Belushi left.’”

Or Chicago’s comedy scene: “You get here and you’re with the funniest of all the groups of friends. Of every town of every group of friends. And you have to work within that and then work your way up.”

Or Twitter’s contribution to comedy: “If you go on Twitter and you make a joke, it’s like, ‘Oh, a thousand other people made that joke. I’ve gotta be better’.”

His brain moves quickly on a winding path that is difficult for an outsider to follow. If there was ever a student of comedy, it’s Shoemaker. He is constantly referencing obscure comedians, explaining how their performances or an interview of theirs inspired him. He keeps his own definition of a joke written on the notepad on his iPhone. He watches “30 Rock” episodes for the sole purpose of breaking down the jokes. He lends me a comedy book to study myself.

“Whenever he’s not doing it, he’s thinking about it,” Hunter tells me about Shoemaker’s comedy pursuits, “whether that be what he can do or what he’s doing wrong.”

When Town Hall Citizens’ show begins, Shoemaker and his six group mates—five guys, one girl—assemble in front of a long black velvet curtain. The room is dark except for this stage area, which is bathed in blue light, as if by a giant computer screen. They flit from scene to scene, with two or three people improvising in each. Shoemaker doesn’t get much performance time and the moments he does aren’t his best. In three months of watching him perform, I’ve almost never seen his timing off. It is tonight. After the show, he sits heavily on the black collapsible chair next to me. His eyes droop and his mouth closes into a tight line. How does he think it went, I ask. Not well, he says. He shakes his head.

Another low on comedy’s emotional roller coaster. So why is it worth it? Why does he continue to pursue the laughter? The week before, he’d explained, “It hits your brain in a certain way that’s very very satisfying. It just feels so good. Man, when you make someone laugh it’s like…” Shoemaker trails off. “And it’s probably something like ‘oh they like me.’”

He says that, unlike other types of performance, there’s no ambiguity about the response. A person can clap politely at the end of a theater piece, having hated the show. Not in comedy. Laughter is a visceral reaction, he points out.

Clinical psychologist Steve Sultanoff says that depression can flow not only from bombing onstage but even when laughter is achieved. When someone links their own value to others’ approval, that person may very well become depressed when they don’t receive it. “For comedians to be comedic in order for people to see them or like them or tend to them or cheer for them would be a way of being able to tell themselves ‘I have value,’” he says.

That’s a natural human response, of course. Everyone likes doing well and receiving praise. The difference is that Shoemaker has committed his life to a craft that requires subjective—and immediate—approval. As he put it: if you don’t get laughs, you lose.

Which is when the self-doubt creeps in, followed by depression. Laughter isn’t a cure, Sultanoff says. It merely offers temporary relief. That’s because the belief—a person needs approval in order to have value—is inherently false. Chasing laughter, while providing momentary happiness, only reinforces this false conviction.

“If I believe I don’t have value and some people act in a way that I do, I feel good,” Sultanoff explains. “But the minute they stop that—stop acting in a way to fill my value—then it leaks out and I’m valueless again.”

The solution, Sultanoff says, is not to stop caring. It is to care and simultaneously realize that others’ opinions do not determine who or how good you are.

It’s healthy for a person to unlink their worth from external factors. But if Shoemaker doesn’t earn laughs onstage, he fails. To try and temper the burn of such occurrences, he’s performing more often and in a variety of comedic formats. The more experiences he has, the less sensitive he is. The less his value is linked to laughter.

For a moment though, imagine climbing onstage, telling a joke and having no one laugh. How would it feel?

For Shoemaker, “it’s the exact same feeling as when you’re sitting in a chair and someone pulls the chair out from under you and you don’t even know it and you fall on the floor,” he says. “Your face turns red, you’re surprised. That happens to me a lot, my face just gets really hot and I’m like ‘oh god what did I just do?””

On the night of Shoemaker’s last level-three class at iO—a large factory-like brick building in Lincoln Park—he is the first student to arrive. Holding his messenger bag tight across his chest, he sweeps into the windowless, rectangular classroom. He is dressed in those same maroon pants and a button-up, but this time in white Vans. Half the classroom is covered by a short wooden stage, the other half by a few rows of collapsible chairs. His thirteen other classmates soon trickle in, one by one, steadily raising the room’s noise level. They are men and women, young and slightly less young, well dressed and sloppy.

The instructor, Jorin Garguilo—an improv veteran with shaggy brown hair, horn-rimmed glasses and a surfer-dude accent—leads them through a series of exercises. Shoemaker and his classmates act out scene after scene, each one representing a different technique they learned during the course. They end by performing a Harold, the twenty-minute improv format that iO created and is famous for.

Once all the acting is done, the students return to their seats or to sprawled-out positions on the floor, leaning against the wall. Standing in the front of the room, Garguilo asks them to share their impressions of the class. What they learned. How they grew. Half a dozen hands shoot into the air. As they share, the stereotype of the happy-go-lucky class clown shatters, answer by answer. No matter how funny they were on stage—and they were very funny—each student exudes a vulnerability when they speak.

One student, a dark-haired, pale-skinned woman, likens the class to therapy. It helped her work through some tough issues in her real life. “It’s making life good, and I’m really sad this is the last class,” she says.

Another female student—tall, blonde, sarcastic—describes how the class helped her see parts of her personality that she’d like to work on, like her tendency to defer to others.

Shoemaker says he learned how to be positive. How to say “yes” to opportunities rather than “no.” “This is literally the best class I’ve ever taken,” he says.

A few days later, I call Garguilo to hear his thoughts about Shoemaker.

“He’s pretty emotional about a lot of his stuff,” he tells me. “All that stuff is really close to the skin for him. He gets upset by things, but he’s very caring and meticulous.” He continues: “I can tell that his mind and his heart are very much enflamed, but it feels like more of a positive than something that is hurting him.”

Back in class, once the comments wind down, Garguilo says a final goodbye and good luck. The students re-wrap themselves in their coats and grab their bags. Shoemaker lingers to chat with his fellow improvisers. Soaking up time in this comedy temple.

A few weeks later, his positivity remains. “I’m just trying to trust that ten years down the road, I’ll be really good at this and even though it’ll maybe feel the same exact way, it won’t look the same,” he says. “It’ll look so much better even if it feels like ‘god I’m so terrible.’ Maybe at that point, my worst then is my best now. That’s what I’m hoping at least.”