Huntington Hartford began life as one of the richest men in America but he wanted to be remembered for more than his money. In this he succeeded only insofar as he became celebrated for the ways he lost it — an extravagantly glamorous life with the stars of Hollywood’s golden age, a disastrous investment in the Bahamas and a much mocked attempt, through his own magazine and museum, to establish himself as a leader of the American art world.

George Huntington Hartford II was named after his grandfather, who co-founded the Great Atlantic & Pacific Tea Co in 1869. By the time of Hartford’s birth in 1911, A&P was one of the most successful retailers in America. Hartford’s two uncles took over the business, opening supermarkets across the US, but his father, Edward, refused to join them, playing the violin and making his own patented shock absorbers instead.

When his grandfather died in 1917, Hartford inherited an estimated $90 million. His gilded childhood was ruled over by his domineering mother, who was determined that Hartford take his place in high society. He was packed off to board at St Paul’s in New Hampshire, a school modelled on Eton where the Wasp establishment disdained his new wealth — even eighty years later he railed against those “six horrible years”.

After Harvard — where, to his mother’s horror, he eloped with a dentist’s daughter from West Virginia — he decided to join the family business. He expected to walk in at the top, but his uncles decided he needed discipline and sent him to count sales of bread and pound cake. He was appalled. “I had an income of over a million dollars a year,” he said in 1991. “Can you imagine me sitting out with a bunch of clerks?” After six months he was fired for skipping work to watch the Harvard-Yale football game.

For the rest of the 1930s he devoted himself to sailing, nightclubs and the pursuit of women. He had a son with a chorus girl, and his wife left him for Douglas Fairbanks Jr. In 1940 he invested $100,000 in the New York newspaper PM on the condition that he was allowed to write for it. Briefly, he tried living on his reporter’s salary, wanting “to inject the element of struggle in my life”, but soon resumed arriving at work in a chauffeur-driven Rolls-Royce. He claimed to have once missed a deadline, returning from an assignment, because there was nowhere to moor his yacht.

During the war he donated the yacht to the Coast Guard and was given command of a supply ship. He ran it aground twice. Afterwards he moved to Los Angeles, founded a modelling agency, was linked to Lana Turner and Marilyn Monroe, and married a young actress, Marjorie Steele (not necessarily in that order). He produced a film for his wife to star in, Face to Face, which garnered decent reviews. He opened Hollywood’s only theatre in 1954, naming it after himself, and founded an artists’ colony in California.

In 1958 he brought to the New York stage his own adaptation of Jane Eyre, starring Errol Flynn. It was savaged by critics, and Flynn walked out saying: “Hartford thinks the lines are immortal and unchangeable. But they’re unspeakable. The play’s a fiasco.”

Though his attention span was notoriously brief, Hartford fancied himself as a thinker. “If I hadn’t had money there is no doubt I would have been a writer,” he said in 1967. “Writing and philosophy have always been my first loves.”

He was certainly consistent in his artistic vision, which reviled Modernism in all its forms, from Picasso to Pollock. He published a pamphlet attacking these trends in 1951, called Has God Been Insulted Here?, and in 1955 paid newspapers to run an editorial, “The public be damned”, equating abstract art with communism. Art or Anarchy? How the Extremists and Exploiters Have Reduced the Fine Arts to Chaos and Commercialism followed in 1964. That year he opened the Huntington Hartford Gallery of Modern Art in Manhattan in an attempt to take on the cultural establishment by promoting realist art. His crusade let to him being dubbed “a new Luther” by a young Tom Wolfe. But, unlike Luther, Hartford made few converts. The gallery cost $7.4 million before he abandoned it in 1969. His arts magazine Show folded in 1973 after losing a similar amount.

By this stage his finances were suffering badly. Investments in shale oil and an automated parking garage came to little. An institute for graphology came and went. His biggest single loss came in the Bahamas, where he bought a deserted island in 1959 and set about building an opulent resort. He renamed it Paradise island, built a splendid hotel, a golf course and gardens modelled on Versailles, and imported a 12th-century cloister from France. But he had neglected to secure a gambling licence, and was outnegotiated by much smarter operators. His $30 million investment became $1 million in seven years.

By the 1970s he had lost his third wife, Diane, to incessant philandering and another slice of his fortune to mismanagement at A&P. In 1974 he married Elaine Kay, a hairdresser 40 years his junior. Although even in his playboy years he never drank alcohol, he now drifted into drug addiction and squalor. In 1982 he was evicted from his Manhattan apartment after Elaine — by now his fourth ex-wife — was charged with tying up his 17-year-old secretary and shaving her head.

In 1989 his biographer, Lisa Rebecca Gubernick, found him living, in and out of consciousness, in a filthy Manhattan townhouse. Her Squandered Fortune (1991) was based on the idea that “how fortunes are lost is just as interesting as how they are made”. By then he had burnt through an estimated $400 million at 1990s prices.

“I spent most of it. I wasted some of it,” he said in his last interview four years ago. “I had a lot of money and now I have enough.” Hartford lived out his last few years in the Bahamas after re-establishing contact with his daughter Juliet in 2004. His first son, whom he never formally acknowledged, committed suicide in 1967. The daughter of his second marriage developed a drug addiction and died in 1988. A son of that marriage survives him, with a daughter from his third.

Huntington Hartford, grocery business heir, was born on April 18, 1911. He died on May 19, 2008, aged 97