Unlike others who inherit great wealth, "Rob wasn't ashamed of being filthy rich," says a friend, though he loathed the artifice and dishonesty of the upper-crust social set in which he was reared. "One story that Rob loved to tell was about a friend who was driving a cab, " says a college pal. "A socialite friend of his mom's got in and asked to be driven to her apartment but said she needed to make another stop. The cabdriver waited for a half hour, and she came out and walked off without a look in his direction. Robbie just loved that, the hypocrisy of it. How this major socialite would screw the little guy without a second thought."

Bingham started writing as a child, and published his first short story in The New Yorker when he was just 26. Much of his fiction focuses on the young disillusioned elite of his world, men and women who move detachedly through their Manhattan duplexes and Nantucket homes and Greek-island cruises. His favorite writer was the globe-trotting existentialist Robert Stone; he also admired Graham Greene, Denis Johnson, and of course, Hemingway, whom he referred to as "Papa." Bingham's best-known story, "The Other Family," which was included in his collection, Pure Slaughter Value, centers on the funeral of a cousin who died of an overdose. "The story didn't come to me in any insider-ish way -- I just found it in a pile of 'Dear Editor' letters," recalls Deb Garrison, at the time a 27-year-old assistant editor at The New Yorker. "I was proud to bring it to senior editors and say, 'This is us -- this is my generation speaking up with a really interesting voice.' "

The Binghams have always been a liberal, philanthropic family, and Rob didn't break from tradition. His generosity was legendary, and he helped many people over the years, often anonymously. He quietly bankrolled endeavors such as the Thread Waxing Space gallery, a photographic archive of Cambodian civil-war victims, the Southern lit-zine The Minus Times. He funded indie movies by promising young directors and collected work by painters just launching their careers. "Rob never asked to look at proposals or budgets or outlines," says conceptual artist Alix Lambert, for whom Bingham funded a documentary about the tattooing practices of Russian prisoners. "One day, he decided to call in a limit order on a stock he had been holding. If the stock hit the order, he said he would sell it all and give the money to my film company. It did, and he did."

Brash, fun-loving, and magnanimous, Bingham was often the life of the party, surrounded by friends, acolytes, and hangers-on who listened attentively as he regaled them with outrageous stories and smiled gratefully when he picked up the tab at Odeon dinners for ten. When friends needed money, he lent them large sums and didn't embarrass them by asking for it back.

Yet as charming as he was, Bingham could also be a loaded gun, a cynic who sprayed bullets indiscriminately when impulse struck. He was thrown out of bars for acting up, had a tendency to comment loudly and crudely on a woman's anatomy, and viciously ridiculed people who didn't meet his standards. "The life Rob spent was perplexing but inspiring, because what he was wrestling with was the truth about society and himself," the writer Thomas Beller observed at his memorial. "Love and fury could surface at any moment."

Much of his fury, friends say, had to do with his family. Like the Kennedys, to whom they are often likened, the Binghams had suffered more than their share of tragedy, and Rob would joke nervously about carrying on the "family curse." In 1964 his uncle John, a Harvard disciple of Timothy Leary's, was electrocuted at the age of 36 while wiring a Kentucky barn. Two years later, his father, Worth, died in a freak accident when Rob was just 3 months old.

Worth was the Bingham family's prodigal son, a good-looking football star with a pronounced party-boy streak who was kicked out of Exeter for drinking when he was 16. One summer morning, while vacationing with his family in Nantucket, he decided to drive to the beach to surf, placing his board horizontally across the backseat of his convertible. When one protruding end hit a parked car, the whole surfboard swung around and crushed his neck.

Following Worth's death, his brother reluctantly took over the family business, an empire that included the Louisville Courier-Journal, the now-defunct Louisville Times, television and radio stations, and a printing house. In a messy, highly publicized battle over the family fortune, the remaining daughter of the family patriarch forced the sale of the newspaper empire in 1986.

Though she remained on the board of the Louisville-based company, Rob's mother, Joan, took her young son and his sister and moved into an apartment in the attic of the Dakota after Worth's death. A well-regarded photographer who is now executive editor of Grove Atlantic Press, Joan tried to stay close to her in-laws, and the entire brood spent summers in Patmos and gathered each Christmas in Louisville at the estate they called the Big House. Joan watched proudly as Mary Bingham, the family matriarch, held recitation contests for her grandchildren: Rob once won $350 for his rendition of "Once More Unto the Breach," from Henry V.

Rob was affected by Worth's death, though he never knew his father. "Men tend to die early, freakish deaths in my family," he wrote in an essay for the online magazine Word. "Being the only male with the last name of Bingham left in my generation, I have some seed-planting issues with which to wrestle. If I am found impotent or die before impregnating someone, there goes the family name."

Joan Bingham was determined to have Robbie take over the newspaper empire, a relative told journalist Marie Brenner in House of Dreams, Brenner's 1988 book on the Bingham family. And though he never got that opportunity, Bingham retained a lifelong interest in journalism. He interned at the Courier-Journal over summers in high school: "I learned how to write my first news story soon after my first ejaculation," he told New York in 1997.