NEW YORK (NYT NEWS SERVICE).- Bruce Jay Friedman, whose early novels, short stories and plays were pioneering examples of modern American black humor, making dark but giggle-inducing sport of the deep, if not pathological, insecurities of his white, male, middle-class and often Jewish protagonists, died on Wednesday at his home in Brooklyn. He was 90.

His son Josh said that the cause had not been determined, but that his father had neuropathy.

Friedman, who also wrote the screenplays for the hit film comedies “Stir Crazy” and “Splash,” was an unusual case in American letters: an essentially comic writer whose work skipped back and forth between literature and pop culture and who, after a decade of early literary stardom, seemed almost to vanish in plain sight.

Like his contemporaries Joseph Heller, Stanley Elkin and Thomas Pynchon, he wrote what came to be called black humor, largely because of an anthology by that name that he edited in 1965. His first two novels, “Stern” (1962) and the best-selling “A Mother’s Kisses” (1964) — tales of New York Jews exploring an America outside the five boroughs — and his first play, the 1967 off-Broadway hit “Scuba Duba,” a sendup of race relations that is set in motion when a Jewish man fears his wife is having an affair with a black spear fisherman, made him widely celebrated. The New York Times Magazine in 1968 declared Friedman “The Hottest Writer of the Year.”

Friedman was again on the cultural radar in the 1970s. His play “Steambath,” which posits the titular location as purgatory and a Puerto Rican towel attendant as God, appeared off-Broadway in 1970 and on public television in 1973. Later that decade he wrote “The Lonely Guy’s Book of Life,” a trenchantly uproarious treatise on adult solitude that began as a series of essays for Esquire magazine and that was adapted by Neil Simon for a 1984 film, “The Lonely Guy,” starring Steve Martin and Charles Grodin.

A deadpan prose stylist with a keen ear for the absurdly self-involved dialogue that emanates from neurosis, Friedman was, at his best, a savage social satirist. He took advantage of the social upheaval he lived through in the 1960s and ’70s to write about race and gender relations from the suddenly uncertain perspective of men like, well, himself, gleefully tweaking the white male psyche’s tenderest spots.

In “Black Angels,” a short story often cited as emblematic of his early and most literary work, the main character, Stefano, is a white man left alone, despairing and struggling to keep up the maintenance on his house after his wife takes their young child and runs off with another man, “an assistant director of daytime TV” (a typically arch Friedmanesque detail). He finds salvation in the form of a team of black yard workers, led by a man named Cotten, who labor for bargain prices.

The story, which takes place almost entirely in Stefano’s fevered and guilt-ridden mind, ends when he invites Cotten in for a beer, begins confessing his problems and places the gardener in the role of a shrink — a service, Cotten says, for which he charges $400 an hour.

In his novel “Stern,” an Air Force veteran moves his family from the city to the suburbs, where a brief anti-Semitic and sexually charged encounter between his wife and a neighbor unleashes a virulent stream of neuroses.

“In the Air Force, Stern, recently married and swiftly packing on hip fat, felt isolated, a nonflying officer in a flying service, at a time when jets were coming in and there was no escaping them,” Friedman wrote.

“The air,” he continued, “was full of strange new jet sounds and the ground reverberated with the throb of them. Somehow Stern connected his nonflying status with his Jewishness, as though flying were a golden, crew-cut, gentile thing while Jewishness was a cautious and scholarly quality that crept into engines and prevented planes from lurching off the ground with recklessness.”

“Stern” was almost universally praised as a shrewd and humorous take on the psychic terrors of seemingly serene suburbia. “A Mother’s Kisses” could be thought of as something of a prequel, the story of a 17-year-old Brooklyn boy whose bulldozing mother arranges his admission to an agricultural college in Kansas and then follows him out there.

“A Mother’s Kisses” was adapted into a stage musical that nearly made it to Broadway (it closed out of town). It introduced readers not only to Joseph, Friedman’s portrait of a lonely, perplexed Jew as a young man, but also to the indomitable Meg, a woman whom Haskel Frankel, writing in The New York Times Book Review and sparing no hyperbole, called “the most unforgettable mother since Medea.”

Friedman followed up with two novels that changed milieus, imbuing both an urban detective (in “The Dick,” 1970) and a cocaine-addled screenwriter (“About Harry Towns,” 1974) with the signature qualities of bafflement and self-questioning. And he continued to write short stories, including “A Change of Plan,” a comic tale about brutal selfishness in which a young man goes on a Florida honeymoon, meets another woman at the hotel pool and ditches his new wife for her.

Adapted by Simon, the story became, as the women’s movement was taking hold in 1972, a highly provocative film, “The Heartbreak Kid,” starring Grodin, Cybill Shepherd and Jeannie Berlin, whose mother, Elaine May, directed. (A 2007 remake, starring Ben Stiller, was directed by Bobby and Peter Farrelly.)

“It hit some kind of chord,” Friedman said to a Key West, Florida, audience in 2005 after reading the story aloud. “I guess maybe it’s not unusual when people are walking down the aisle for an instant to flash on the possibility that maybe they’re making a mistake. Maybe there’s someone else. I know it happened to me.

“People ask where do stories come from,” he continued. “Well, they come from a lot of places. Very often it’s your life, and then you extrapolate from a personal experience. In my case, yeah, OK, I got married, went down to Florida, we were exhausted, my wife fell asleep, I went down to the pool and I saw a very pretty girl. And I said, ‘Oh, God.’ And I did tell her I was a little married, and she just splashed some water at me. That pretty much ended it. I went back into the marriage, had three children. And then got divorced.

“But that’s how a story will happen. You have a fragment of an experience and ask yourself, ‘What if?’”

Bruce Jay Friedman was born on April 26, 1930, and grew up, along with his sister, Dollie, in a three-room apartment in the Bronx, much like the crowded one in Brooklyn he described in “A Mother’s Kisses.” His father, Irving, worked for a women’s apparel company; his mother, Molly, a confident woman with a feisty patter and a devoted theatergoer who was described by a friend of Bruce’s as “someone looking like a middle-aged Jewish Rita Hayworth,” was evidently the model for Meg.

(Sample dialogue from “Lucky Bruce,” his 2011 memoir: When a teenage Bruce Friedman contracted gangrene in his left arm, a doctor who had amputated the limbs of soldiers during World War II wanted to saw it off. “I have a better idea,” Molly Friedman said. “I’ll saw off your head.”)

After graduating from DeWitt Clinton High School and, like Joseph, failing to get into Columbia University, he went to the University of Missouri, where he studied journalism. He spent two years in the Air Force, during which he wrote for a military publication called Air Training.

Shortly after returning to the Bronx, Friedman sold his first short story, “Wonderful Golden Rule Days,” about a boy making his discomforting way in a new school, to The New Yorker. He took a job with a company called Magazine Management and rose to become editor of somewhat cheesy men’s adventure publications with names like Male, Men’s World, Men and True Action.

Among the dozens of freelance writers he hired was Mario Puzo, who became a lifelong friend. As Puzo was writing “The Godfather,” Friedman recalled, he asked Friedman what he thought of the title.

“Not much,” Friedman told him. “Sounds domestic. I’d give it another try.”

Friedman’s first marriage, to Ginger Howard, ended in divorce. In addition to his son Josh, he is survived by their two other sons, Kipp and Drew, the cartoonist; his wife, Patricia O’Donohue; their daughter, Molly Stout; and three grandchildren. His sister, Dolly, died a few years ago.

After the 1970s, Friedman turned much of his attention to the movies. “Stir Crazy,” a buddy comedy set primarily in a prison, starring Gene Wilder and Richard Pryor and directed by Sidney Poitier, became the third-highest domestically grossing film of 1980. He later wrote the first draft of “Splash,” the 1984 romantic comedy about a love affair between a man (Tom Hanks) and a mermaid (Daryl Hannah), eventually sharing screen credit and an Academy Award nomination with Brian Grazer, Lowell Ganz and Babaloo Mandel.

Friedman wrote several more novels, including “Tokyo Woes” (1985), about an American gadabout’s adventures in Japan; “The Current Climate” (1989), a revisit to Harry Towns; and “A Father’s Kisses” (1996), about an unemployed poultry distributor who becomes a hit man. Though they all received respectful reviews, critics failed to find in them the freshness of his early work. He also had small roles in several films, including three directed by Woody Allen: “Another Woman” (1988), “Husbands and Wives” (1992) and “Celebrity” (1998).

Friedman had a wide circle of celebrity friends and acquaintances from both the literary and movie worlds; his name-dropping but good-natured and often self-deprecating memoir is dotted with anecdotes about Warren Beatty, Natalie Wood, Norman Mailer, Isaac Bashevis Singer, Joseph Heller (who was an especially close friend) and many others. Friedman often spoke in interviews about the conflict between writing screenplays for the money and the fun of it, and the higher calling of writing novels.

“The truth is, I tortured myself by moving back and forth, from one to the other,” he wrote in “Lucky Bruce,” in which he also acknowledged the career arc that started at the top and declined.

“Stories, quite a few of them, got written and published,” he wrote of the later years of his writing life. “If they lacked energy (were less frantic?) I assured myself they were more ‘dimensional.’ Once I discovered that comforting description, I clung to it like life itself. There were a few books, some plays that still need attention. And quite a few pieces about me in the literary journals, wondering what had happened to me.

“Where had I gone? I began to feel like the most (fondly) remembered forgotten writer in America.”

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