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A majority of the music video for John Mellencamp’s 1982 hit “Hurts So Good” is shot inside a drab store in Medora, Ind.. In the video, Mellencamp dance-humps a young woman wearing a black leather onesie atop a table. As they writhe, the crooner lets out: Lord knows there are things we can do, baby/ Just me and you. Below, a throng of bikers move to the music in concert with the lyrics. In the next scene, Mellencamp, then 30 years old and going by “Cougar,” juts out of the store and thrusts his crotchless chaps toward the camera. Finally, at dusk, the music video comes to an end as Mellencamp navigates the gang on a motorcycle ride through Medora’s flat, winding roads.

It wasn’t until 2009, when New York Times columnist John Branch profiled the plight of the Medora Hornets, the local high-school basketball team, that the town was placed back into the spotlight, so to speak. This time, Medora, a town of about 700, wasn’t depicted through the feel-good, super-sexual gaze of a local rock star. Instead, Branch reported on a downtrodden rural Midwest town that had little to celebrate. “In these depressed times,” wrote Branch, “there is little to cheer but the high-school basketball team. Except it does not win.”

The article got the attention of filmmakers Davy Rothbart and Andrew Cohn, old friends and self-proclaimed “documentary junkies” who decided that it was their destiny to film the 2010-2011 Medora Hornets’ season. The day after they read it, Rothbart and Cohn drove five and a half hours from Ann Arbor, Mich., to Medora and stayed. Over the course of a year Rothbart and Cohn’s crew shot over 600 hours of footage, often working 10-hour-plus days, seven days a week, before retiring to a room at a Travelodge in neighboring Seymour (Mellencamp’s hometown) to slug a few beers and recap. In all, the 80-minute final cut, Medora, which was produced by Steve Buscemi and Stanley Tucci—post-production was funded by a Kickstarter campaign—took three years to complete and premiered at SXSW in 2013. Cohn calls it something of an “anti-sports movie.”

On the surface, Medora is a classic sports film with an underdog narrative hook: Against all odds, a high-school basketball team from southern Indiana (Larry Bird and Hoosiers land) searches for a way to break a losing streak. But what makes Medora most captivating, in addition to the potential for one team victory, are the interconnected stories of many of the individual members of the team who are going through the trials of adolescence under often grim circumstances. “Poverty rates are high here, college graduates few,” wrote Branch. “Drug use is rampant, several said”—meth, e.g.—“and many residents live in ramshackle trailer homes strewn about the hills that surround the checkerboard streets of the town.”

With Medora, Rothbart, 39, continues to tell the stories he loves most: humorous, emotional tales about lost, fucked-up Americans, often young men, who get fucked up and fucked over. One of the film’s main characters, Dylan, whom Rothbart grew close with, would sometimes forget to tell the girls he’d pick up for dates that the co-director would be accompanying them with a camera. Their reactions, said Rothbart, would be something along the lines of, “Who’s that dude in your backseat?”

“Of course I found myself relating to these kids in certain ways,” said Rothbart, who has laid out a personal history of his own pursuit of love as a young adult in My Heart Is an Idiot, a book of personal essays that he penned while working on Medora. Rothbart, like the Medora ballers, longs for redemption, for a place to call home. But he knows that many of his best stories, and relationships, have been forged on the road—he just completed his 13th tour around the United States promoting his film—so that’s likely where he’ll remain.

***

On May 2, Rothbart took the stage at the Michigan Theater in Ann Arbor, a few blocks from the University of Michigan hospital, where he was born, and a 20-minute car ride from where he grew up, at Packard and Carpenter, near the White Castle. Eighteen years ago, Rothbart, an English and Creative Writing major at University of Michigan, was a 21-year old Wolverine. Now Rothbart—who since graduating has become a radio and print journalist, a publisher, author, and filmmaker—was there to show the class of 2014 how he made it in the mad, wide world. “I’ve been arrested six times,” began Rothbart as he nipped Maker’s Mark from a plastic Gatorade bottle. “I’ve got 12 ideas to share with you,” he said. “Call it a 12-Step Program … English Majors’ Anonymous.”

After graduating, Rothbart moved to Chicago and endured a four-year stretch during which he didn’t kiss, let alone have sex with, a girl, opting instead to yearn for an ex who’d long forgotten about him. (She eventually married a French windmill repairman named Gilles in Toulouse.) He said they were the hardest years of his life. “The first two years, you’re just crying every night in your bedroom, and no one wants to have sex with you while you’re crying,” he said. “Then the next two years, you’re semi over it, and you’re trying to kiss anyone who crosses your path.” During that stretch Rothbart saved money by working as a pizza deliveryman, as a valet at a bar, at a video store, and as a ticket scalper, often dealing in the dead of the winter in the Second City. (Four of his arrests are from scalping.)

But he saved up money and, inspired by the love he felt for a character named Shade from the movie Gas Food Lodging, moved to the mountains of New Mexico to write. “It was lonely there sometimes,” Rothbart told the audience. “But that’s what a Vision Quest is for—to veer straight into the black hole of loneliness, and whatever else you’re wrestling with—and face that shit head on.” Out of it came his first collection of stories, The Lone Surfer of Montana, Kansas.

In the desert he also became a dedicated NPR listener, and through a connection to the show This American Life with Ira Glass, he applied to be a producer. So he put together a “1000 percent honest” résumé and sent it in. “I put down pizza delivery, valet, ticket scalper, marijuana salesman,” said Rothbart, “including some of the volunteer work I’d done, too, like teaching creative writing in prisons.” Three days later Glass called Rothbart in New Mexico. And although he was not ultimately selected (he made it to the final three, he said), Rothbart has since produced about one story a year for NPR over the last 10 years.

In 2007, five years before My Heart Is An Idiot was released, Glass made an appearance in the trailer for Rothbart’s eponymously titled documentary, a cinematic lead-in of sorts to his collection of essays. Advertised as a film for the “terminally romantic”—the preview’s interviewees surmise that Rothbart’s romantic experiences as an adult remain akin to a 22-year-old’s—Glass’s endorsement comes in a similar form, as he asserts: “You’re saying that the question you’re facing is: Are you just fucked up?”

In Rothbart’s story “Shade,” from the book, he traveled to Arizona to meet a young woman named Sarah he’d never met, but, having attributed her to the notion of Shade—the perfect woman with whom he’d be content to the end of time—he was hopeful (and likely horny). When Rothbart and Sarah meet, he finds she is digging him, at one point calling him her boyfriend. But Rothbart was not into her. (In fact during one scene, he fantasized about Sarah’s friend Ivy whom he was “hot for.”) But he plays along as best he can as they drive together, as planned, through Arizona, toward New Mexico, while the protagonist plots a way out. Before the story delves into a situation wherein Rothbart finds himself hurling a bloody section of elk roadkill off a road, the author seems to hit upon the answer to Glass’ question:

And the truth was, it wasn’t personal, not exactly. It wasn’t her fault that I’d built her up as some kind of idealized soulmate. What I craved and had been chasing, again and again, for the past eleven years, I began to realize, was the exquisite mystery I’d felt when I’d first seen Shade on the screen. That wrenching longing was its own perfect drug, and as long as a girl kept me at arm’s length and maintained a distance, some veil of mystery—as … all the others had—then my excruciating ache could be preserved. But when a girl threw open the gates and let me in, as Sarah had, no matter how charming, smart, and pretty they might be, the intensity would drain from me and I wouldn’t be able to gas it out of there quickly enough and start my search for the next girl to call Shade.

***

In 1999, while Rothbart was still living in Chicago, he found a handwritten note on the windshield of his car that would change the course of his life forever. It read:

   Mario—
I fucking hate you you said you had to work then whys
your car HERE at HER place??
You’re a fucking liar I hate you I fucking hate you
Amber
PS Page Me Later

When Rothbart—who for years had been collecting discarded notes, allured by their mystery—showed his friends the Mario/Amber note, which had been misplaced into his life, they not only got a kick out of it, but communicated to him that they too had a number of found items of their own to share—random drawings, to-do lists, photo, receipts, etc.—that needed a home. Rothbart knew he was onto something so, at the age of 26, he moved in with his parents to focus his energies into his new creative project: piecing together these mysterious relics of otherwise trash, strewn about the world.

Back at home in Ann Arbor, though Rothbart had “a hard time macking on girls,” he grew closer with his parents. His mother, who is deaf and a spiritual counselor, is the subject of the opening story in My Heart Is an Idiot, “Bigger and Deafer.” In it, Rothbart took advantage of the mother’s deafness in order to listen to the music he wanted (N.W.A., e.g.), get out of trouble at school, eat more chocolate chip cookies, and hang out with friends. Rothbart’s brother Peter was in on it too, and at one point, their father as well. From his parents, Rothbart says that he inherited their “curiosity of people we share the world with” as well as their “off-kilter” sense of humor.

A number of Rothbart’s tales in My Heart Is an Idiot derive from his time in Ann Arbor, including “Ninety-Nine Bottles Of Pee On The Wall,” a batty tale wherein Rothbart, relegated to his room because of a shattered ankle, decides to pee in bottles—ultimately, 99 of them—rather than truck to a bathroom. The plot of the story rests upon Rothbart traveling across the country to potentially use his fermented, bottled urine as a weapon of revenge on a literary scam artist. Rothbart asked his father to introduce this particular story, via video, in a straightforward fashion. “He was like, well, I wrote this rap,” said Rothbart. “He’s a rapping fool. He will rap anytime, anywhere.”

In June 2001, Rothbart and co-founder Jason Bittner put together issue no. 1 of Found magazine, with the help of Rothbart’s 12- and 18-year old cousins, and scissors and tape. Within a few weeks Found had sold 800 copies that he’d made at Kinko’s. And the more people read it, the more submissions were received, about 10 to 20 each day. Within a year Rothbart had signed a book contract with Simon & Schuster, and a year after that he embarked on a 50-state book tour with Peter, a musician. In the fall of 2013, Rothbart finished up his 13th Found magazine tour.

During the tour he even stopped by Letterman to promote the soon-to-be best-seller, which also recently became the basis of a hit musical in New York. Dressed in a hoodie and checkered pants, Rothbart told the late-night legend about his 136-city tour. “We bought this ’99 Dodge Ram on eBay,” he offered Letterman. “Have you ever lived out of a van?” The host pursed his lips and paused, as the crowd chuckled. “It’s on my to-do list,” Letterman replied.

Over the next few minutes, as Letterman held up mounted Found notes, Rothbart provided context. The camera zooms in to a printed-out list of monthly expenses. “If you’re broke, you make a list,” Rothbart explained.

RENT: $600
CELL PHONE 50
CABLE 60
BUZ / TAXI 60
FOOD 500
LIQUOR 600 [the crowd cracks up, rising from here on out]
LAUNDRY 50
CRACK 600
ATTORNEY 250
MISC 200
ASVINGS [sic] 100

Letterman: “So that’s a responsible guy, putting one-hundred bucks away in savings every month.”

***

Rothbart and Cohn met playing pick-up on the basketball courts of Ann Arbor. When they played on the same team, Rothbart ran the point while Cohn played point-forward, a position—now played by LeBron James—that Rothbart says Cohn “invented.” At the time, Rothbart had already graduated from University of Michigan and was working on what would become Found. “Davy taught me just about everything I know about storytelling,” said Cohn. “Our sensibilities are the same. We care about underdogs.”

After Medora was released, Rothbart and Cohn brought the players, usually two at time, around the country—L.A., San Francisco, New York City, and Ann Arbor, among them. “Most of them had never been outside the state of Indiana,” said Rothbart. “Most of these kids—they’d never been on a plane before.” In Michigan, Rothbart took Medora players Dylan and Zack, whose family had taken in another player, Rusty, when he left home, to his parents’ house, and to hang out with his hometown friends. That, says Rothbart, “was really special.”

On the eve of the New York premiere of Medora, Dylan and Rusty walked around lower Manhattan with a basketball in hand, dribbling it, spinning it, shooting it, before getting a sandwich at Katz’s Deli. Years earlier, had the Medora boys been in that exact location, they might have seen a guy running naked toward them, having woken up minutes before on a park bench on his birthday. It would’ve been Davy.

A pivotal moment in Medora occurs when Rusty is pressured at a party by one of his best friends, Zack, who is two sheets to the wind. “C’mon now,” says Zack to Rusty as he lies on a bed, relaxing and sober, with a girl. “He’s mad at me ’cause I’m not drinking,” Rusty says. “I’m proud of you,” says the girl, and gives him a kiss on the cheek. “Be proud, bro,” says Zack as he walks out of the room. Donning a Strap On A Pair Nike logo shirt, Zack turns back. “I’ll have fun whatever I’m doing, just be proud whatever the fuck.”

The decision to include this bit in the film, says Rothbart, is important because it shows that Rusty, despite generations of alcoholism in his family, has the power to overcome it and make a positive decision. I wonder, however, if Rothbart worries about negatively influencing the Medora kids, considering he habitually drinks in many of his stories, at times behind the wheel. I wonder if he feels the need to protect them, especially Dylan, who searches for a relationship with his father throughout Medora. “We talk about real-life stuff,” said Rothbart. “I’ve been [to Medora], seen in their homes, difficult things for them. So it’s only fair for them to know me as raw and intimately as I know them. I’m not necessarily a role model. I’m a friend.”

But I imagine that Rothbart, who said that his “heart is less of an idiot than it has ever been,” is growing into the skin of raconteur whose work, for all of the foibles it examines, is intended to teach life lessons. At the Michigan graduation, Rothbart dropped some final knowledge on the baby Wolverines:

I’m like what, 15 years, 18 years older than you all. I haven’t mastered life, I haven’t figured shit out, in fact, what would probably be most helpful for me is if I could take a seat out there by myself, and all of you could come up here and give me advice.

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