Richard Shepard has scarcely been in St. Louis four hours before he finds himself surrounded by a bevy of journalists, a roundtable of tape recorders facing him like antes at a poker game. Sitting on the rooftop of Clayton’s Bonhomme on the Park on a breezy afternoon, Shepard revels in the attention.

The New York director has reason to be cheery. His latest effort, the black comedy The Matador, which he wrote and directed, premiered at Sundance to thumbs-up reviews and a $7.5 million distribution deal with Miramax. For a Hollywood exile who claims he’s been in “movie jail” for nearly 20 years, it appears that Shepard has served out his sentence.

“It’s totally fun except when it’s completely miserable,” Shepard says in reference to moviemaking. “Is somebody going to make this movie? Will the money come together? Are the actors going to be assholes? Is anyone going to like it?” Shepard grins. “Last year my chest hair went white.”

If anything, Shepard’s exile was part of a greater good. “If I had become successful when I was 25, I would’ve been impossible,” he explains, talking as much with his hands as his mouth, leading a make-believe symphony through Beethoven’s Ode to Joy. With his rolled-up jeans, faded sneakers, spiky hair, and boyish charm, Shepard resembles a character from a John Hughes movie all grown up, Ducky going gray.

As a preteen inspired by King Kong, Shepard recalls asking his parents for a movie camera for his birthday. “I realized that I wasn’t good at baseball,” he says. Shepard attended NYU but didn’t graduate. Instead, he moved to Los Angeles where he shot his first film at 24. The hype was overwhelming. Agents and studio execs flocked to the premiere. Shepard found himself at lavish Hollywood parties where he hobnobbed with movie stars and studio heads. Variety called him “a little Scorsese.”

The film that inspired all the hoopla was The Linguini Incident, starring David Bowie and Rosanna Arquette. It would prove to be, if not career suicide, at least coma-inducing. “I was finished before I began,” Shepard admits. “Everyone who saw it hated it. Agents ran from me like roaches, the studios wouldn’t return my calls. I was 25 and couldn’t get a job.”

Because he was too embarrassed to wait tables where he might serve the same agents who once courted him, Shepard descended into depression, alcoholism, and shoplifting. After two years he finally dragged himself off the couch. He used this time off the roster to learn how to be both a businessman and a producer, how to read a 45-page contract and shoot a film for under 50 thousand. He took to writing his own scripts—by the simple logic that no one was sending him any.

Shepard also endured a brief stint shooting Inside Out, a soft-core porn serial for the Playboy network, where he wasn’t the only player down on his luck clocking in for the paycheck. The “weird concentration of talent” included the future producer of Six Feet Under, the future director of About Schmidt and Sideways, and the future cinematographer of Memento and Batman Begins. The Inside Out crew received three pithy notes from Hugh Hefner. “The first said, ‘Congratulations, can’t wait to see the show.’ The next one said, ‘Love the show, wish the stories were less smart and more sexy.’ The third one said, ‘You’re canceled.’” Shepard shrugs. “You can catch it on DVD if you want to torture yourself.”

Eventually Shepard redeemed himself by shooting a string of below-the-radar indies whose names you wouldn’t recognize, winning acclaim in artsy circles and starring more unknown talents who would soon become famous, such as Oscar winner Adrien Brody.

Shepard’s next project was The Matador, an offbeat buddy comedy about a hit man in Mexico having a midlife crisis who crosses paths with a struggling salesman. Shepard figured he could shoot it on digital video for a pittance. Then Pierce Brosnan’s production company got hold of it, and once the former James Bond signed on as the star, the budget shot skyward. The highlight came when Shepard convinced a buffed-down Brosnan that donning a cheerleading outfit in one scene, and strolling through a hotel in briefs and boots in another, would be a good career move.

Shepard’s hunch may prove correct. The Matador won the Audience Award at the San Diego Film Festival. So far, the 12-city press junket has taken Shepard from California to New York, with stops in London and Deauville, France.

“When I hear of directors who don’t go to festivals, I think they’re…” Shepard seems to be searching for a G-rated adjective. “Stupid.”

This fall, Shepard was asked to direct the pilot episode of CBS’ Criminal Minds, starring Mandy Patinkin. Meanwhile he’s written a new script, Spring Break in Bosnia, a drama that follows a group of journalists mistaken for CIA agents in their half-hearted attempt to catch a war criminal charged with ethnic cleansing. The impetus came from an article Shepard read in Esquire. He hopes to start filming by summer.