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Dan Greenburg, who gained a national following with his irreverent, mordantly funny books about sex, marriage and Jewish mothers, then reached a far younger audience with chapter books about paranormal adventures and a math-averse superhero named Maximum Boy, died Dec. 18 at a hospice center in the Bronx. He was 87.
The cause was complications of a stroke he had last year, said his son, journalist and author Zack O'Malley Greenburg.
A onetime industrial designer with a fondness for tongue-in-cheek humor, Mr. Greenburg wrote more than 70 books but was probably best known for his first, the 1964 bestseller "How to Be a Jewish Mother: A Very Lovely Training Manual." The satirical self-help guide sought to answer such pressing questions as "How many miles away should you allow your child to move?" (the answer came in the form of a math equation: "Distance = M.P.H. x Lambchop Defrosting Time"), elucidated culinary techniques like the "Proper Form for Administering the Second Helping" and featured a glossary for terms such as "unmarried surgeon: the answer to a mother's prayer."
"Give your son Marvin two sports shirts as a present," Mr. Greenburg advised in one chapter. "The first time he wears one of them, look at him sadly and say in your Basic Tone of Voice: 'The other one you didn't like?' "
While Borscht Belt comedians had long poked fun at the image of the anxious, overbearing Jewish mother, Mr. Greenburg's book reached a wider audience, selling more than 270,000 copies in its first year alone. The book "established the Jewish mother as a nationally and internationally recognized stereotype," according to "You Never Call! You Never Write!: A History of the Jewish Mother," by Joyce Antler. It was adapted into a hit 1965 comedy album by actress Gertrude Berg, and two years later it made its way to Broadway in the form of a short-lived musical revue.
Mr. Greenburg noted that the use of guilt as a parenting device was widespread, or at least not uncommon. "You don't have to be Jewish or a mother to be a 'Jewish mother,' " he said. But his jokes led some detractors to accuse him of promoting misogynistic or antisemitic tropes, and his own mother questioned the book's basic premise. (She did agree to be featured on the back cover, spoon-feeding the 28-year-old author in a photo. "He is still unmarried," the text read, "and does not know how to stand up straight or eat properly.")
The book's success launched Mr. Greenburg on a nearly six-decade writing career, leading to the publication of satirical works such as "How to Make Yourself Miserable" (1966) as well as the occasional crime thriller. Mr. Greenburg adapted one of his madcap comic novels, "Kiss My Firm But Pliant Lips" (1965), into the screenplay for an Elvis Presley musical, "Live a Little, Love a Little" (1968), though he noted that it was probably the worst movie Elvis ever made.
He also did stand-up comedy (he once opened for Bette Midler), appeared on "Late Night With David Letterman," wrote a pair of 1980s sex comedies (the movies "Private Lessons" and "Private School") and penned one-act plays such as "Arf" (1969), which was staged off-Broadway and starred Paula Prentiss as a dog frantically trying to become a human woman.
The reviews were not kind, but later that year he had more success with "Oh! Calcutta!," a nude song-and-dance show created by Kenneth Tynan that featured material from Mr. Greenburg and nearly a dozen other writers, including Sam Shepard and John Lennon. A 1976 revival became one of the longest-running shows in Broadway history.
Mr. Greenburg drew on the chaotic mishegoss of his life for books such as "Scoring" (1972), a cheeky account of his sexual misadventures, including in the years leading up to his 1967 marriage to journalist Nora Ephron, who turned to screenwriting and directing after their divorce. (By all accounts, their separation was amicable; Ephron would later say of Mr. Greenburg, in her autobiographical novel "Heartburn," that he "was so neat he put hospital corners on the newspaper he lined the hamster cage with.")
As he told it, that book and many of his others were fueled in large part by fear. "I'm a coward," he wrote in "True Adventures" (1985), a collection of pieces he wrote for magazines including Life, Playboy and New York. "There is nothing in my life, no matter how benign or banal, whose contemplation cannot, if I'm given sufficient time to brood about it, fill me with dread." That included getting out of bed in the morning and interacting with the opposite sex.
Mr. Greenburg eventually fashioned himself as a literary thrill-seeker, deciding that it would be better for both his personal and professional life if he faced his fears head-on, then wrote about it. To that end, he drove around with New York homicide detectives, followed firefighters into burning buildings, flew upside down with a stunt pilot over the Pacific Ocean, joined a Japanese expedition in search of the Loch Ness monster, spent a week at a tiger ranch in Texas and participated in an orgy for Playboy, an experience he considered genuinely terrifying (and also quite funny).
Many of his adventures served as the basis for his children's books, which became a focus in the mid-1990s after he launched "The Zack Files," a series of fantastical chapter books - including "Dr. Jekyll, Orthodontist" and the Pinocchioesque "Tell a Lie and Your Butt Will Grow" - about a 10-year-old boy modeled after his son.
The books proved popular with young readers and led to other series, including "Dripping Fang," about 10-year-old orphans whose father drowned in a port-a-potty and whose mother was smothered by a colony of angry rabbits. Another series was more autobiographical, following the adventures of Maximum Boy, an 11-year-old with super powers. Mr. Greenburg didn't have the speed or strength of his young protagonist, though he noted that he did grow up as a skinny Jewish boy on the North Side of Chicago, wore glasses, was lactose intolerant and, like his fictional alter ego, seemed to lose all hope when confronted with math problems.
The older of two children, Daniel Greenburg was born in Chicago on June 20, 1936. His parents were Jewish immigrants from Eastern Europe, his mother a schoolteacher from Lithuania and his father an artist from present-day Ukraine.
Mr. Greenburg studied fine arts and industrial design at the University of Illinois, where he began writing after reading J.D. Salinger's "The Catcher in the Rye." One of his first pieces was a parody of "Goldilocks and the Three Bears," written in the style of three different authors: Salinger ("Catch Her in the Oatmeal"), James Joyce ("Portrait of Goldilocks as a Young Girl") and Ernest Hemingway ("A Farewell to Porridge").
The piece was published by Esquire in 1958, shortly before Mr. Greenburg graduated college, and led to a second story for the magazine, this one a reworked version of "Hansel and Gretel" in the style of Samuel Beckett, Jack Kerouac and Vladimir Nabokov.
Mr. Greenburg moved to Los Angeles, where he continued to write while also earning a master's degree in industrial design from UCLA in 1960 and working as a copywriter at advertising firms.
By 1962 he had moved to New York, where he became the managing editor of Eros, a literary quarterly about sex and love that catered to the sort of reader who subscribed to Playboy as well as the Paris Review. He lasted only about six months at the magazine. By the time he left he had gotten the inspiration for his first book, while talking over lunch with his boss, editor and publisher Ralph Ginzburg, about how "we essentially had the same Jewish mother urging us to eat."
After his divorce from Ephron, Mr. Greenburg married writer Suzanne O'Malley in 1980. That marriage also ended in divorce. In 1998, he married children's writer Judith Wilson, with whom he lived in Hastings-on-Hudson, N.Y.
Survivors include his wife; his son, Zack, from his second marriage; and a granddaughter.
Mr. Greenburg admitted that after he began writing children's books, he missed some of the media attention he got for his earlier books for adults. But he said that he had never been happier, and in recent years was working on a new series about famous historical figures, written from the perspective of their cats.
"It's the most fun I ever had in my life," he told the New York Times in 1998, reflecting on his work for children. "There's nothing more fulfilling than hearing that you've turned a kid on to books. That's enough for a career right there."
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