To suggest that Richard Lewis is chronically depressed would be like saying that Donald Trump has some spare change. We're talking serious understatement. We're talking about a comic who has achieved considerable success (31 appearances on David Letterman's show; named to one magazine's list of "the most influential American humorists in the 20th century") by constantly mourning his misspent life. His clothes mark the man: Lewis hardly owns a single garment that isn't black. One closet in his Los Angeles penthouse apartment holds 15—count them—15 black overcoats. There are also a black TV in the house, a black exercise bike, black desk, black easy chair, two black sofas—and a black Jaguar in the garage.

If they dare, cable audiences can take a full-scale tour of Lewis' tenebrous psyche starting this Saturday, June 18, when his I'm Exhausted special debuts on HBO. Featuring about 50 minutes of stand-up comedy—though onstage Lewis always looks like he's trying to lie down, preferably on a therapist's couch—the hour-long show climaxes when Richard suffers a nervous breakdown on-camera and is carted off to a mental institution, where he's visited by Larry King, Garry Shandling, Steve Allen, Jackie Collins, a contortionist and the Savior. "I worked really hard on the show," says Lewis. "Particularly the nervous breakdown. It was 17 years in the making."

Oh, longer, much longer. Such fine whine is well aged, and, to hear Lewis, 39, tell it, he was a prime candidate for psychiatric intervention from the cradle. Born two months prematurely, he says he was "thrown against my will into an incubator. I had to share it with these two neurotic babies who were revolving around on this spit along with me to get done."

Soon after Lewis, the youngest of three, was "done," his family moved from Brooklyn to Englewood, N.J., where his father, Bill, ran a catering service. "He was the greatest caterer who ever lived, the Babe Ruth of caterers," says Richard, who speaks of his father with teary-eyed reverence. Lewis was so distraught at his father's death in 1971 that he made his first, and by no means his last, foray into therapy. Since then, he estimates, he has spent a Woody Allenesque fortune—he estimates $200,000—on analysis. "I don't really know how much therapy he's been through," says his mother, Blanche, a regional-theater actress for the last 13 years who now lives in Hackensack, N.J. "But I think he'll be able to cut loose from it if he ever meets the right girl."

On his way to becoming a comic, Lewis passed through some oft-traveled stages: a guilt-ridden childhood, years as an unspectacular student and recidivism as a disciplinary problem in high school. After graduating from Ohio State University in 1970 with a marketing degree, he got a job as an advertising copywriter in New Jersey. Out of boredom, he started slipping jokes into his ad copy, then began driving into New York to hang out at the Improvisation with the likes of Freddie Prinze and David Brenner. After juggling the two interests, it was goodbye ad biz, hello showbiz.

"Richard was unbelievably neurotic," says his friend Jay Leno, whose Boston apartment was Lewis' crash pad when he played Beantown in those early days. "Admittedly my apartment was not the cleanest in the world," says Leno, "but he would come for a weekend and bring cleaning supplies—Lysol and tile cleaner."

Lewis had little success burnishing Leno's apartment, but he's cleaning up with his act. After a long tour of the comedy-club circuit, he now plays approximately 50 concert dates a year, earning an income in the mid-six figures. His performance always features a finely timed crescendo of pain and paranoia. Dressed in trademark black, Lewis stalks the stage, hunched over, one hand clutching the microphone, the other brushing back his long black hair as he regales the audience with tales of his "dates from hell," his endless physical ailments and traumatic family encounters.

"My grandparents were depressed-again Jews," begins one such routine. "They had a bumper sticker that said, 'I'd rather be weeping.' They had one of the first satellite dishes over their condo—it picked up problems from other families. My grandfather would take home movies and edit out the joy. Then he'd put in a cry track. Our favorite party game at home was 'Pin the Blame on the Donkey.' "

Lewis suffers at least as much angst offstage as he does on. His life has been an endless succession of bad relationships with women, a situation he attributes partly to his tendency to get involved with actresses ("I'm seduced by people who are narcissistic. I'm in the Fool Hall of Fame"), partly to a belief that he's too short (for the record, he's 5'9½"). "I'm 5'10" when I feel good," he says, "but I've sunk below 4' with some women. I was 3'11" in my last relationship. Maybe it's just my bad posture." His notoriety as a troubled lover has led to two appearances on Dr. Ruth's show. "The last time I was on, she said I cared too much about what people thought," says Lewis, "and that she was against me going out with narcissistic women and that I would never find anybody because I was looking for people who would abandon me. I started weeping when she said that."

Though it sounds unlikely, he might be crying a little less lately. For the past five months, Lewis has been going out with a 27-year-old actress (of course) whom he met on a club date in Manhattan. If the current relationship hits the skids, however, Lewis will keep on looking. "I feel the ideal woman is me in drag," he says. "I'm the only one I can get along with. If I could figure out how to marry myself, I would." Good idea. After all, why make two people miserable?

—By Joanne Kaufman, with Michael Alexander in Los Angeles