10 of the Richest Cheapskates of All Time

(1889 – 1977)

The great silent movie comic was never quieter than when the time came to buy another round or the waiter appeared with the check. This despite the fact that he was reportedly earning $10,000 a week by 1916, the equivalent of $219,000 a week today. “Even after he had millions in the bank,” biographer Kenneth S. Lynn observed, “Chaplin never seemed to have any money on him, and when dining out with friends he always allowed someone else to pick up the tab.“

Actor Marlon Brando called him “an egotistical tyrant and a penny-pincher,” while Orson Welles upped the ante to “cheapest man who ever lived.” According to Hollywood lore, Chaplin borrowed movie-set carpenters to build his home in Beverly Hills in order to save money, resulting in a structure so flimsy and prone to falling apart that it was soon nicknamed Breakaway House.

(1892 – 1976)

Believed to be the world’s richest private citizen in his day, the oft-married and oft-divorced billionaire oilman loved hanging with the international jet set but hated paying for his ticket. Biographer Robert Lenzer reports that while Getty stayed in fashionable hotels, he typically booked the smallest and cheapest rooms available, and could be found “living out of a suitcase and conducting his business out of shoeboxes.”

When he acquired a mansion outside London, observers might have thought he was loosening up a bit, but papers soon reported that he had installed a payphone for the use of guests, while also putting locks on all the other phones. Getty didn’t deny it, but instead devoted pages of his autobiography to a spirited but less than convincing defense.

Among his excuses: He didn’t personally own the home. His company did, so he was really just looking after the interests of shareholders. He dismissed the tale as “a story to warm the hearts of all who take orgiastic delight in picturing the rich as inhospitable, ungracious penny-pinchers,” adding with perhaps uncharacteristic generosity, “I can’t really bring myself to begrudge them their pleasure.”

(1904 – 1986)

Suave, funny, good-looking and cheap, cheap, cheap, Cary Grant (born Archibald Leach) grew up in modest circumstances in England before coming to the U.S. in his teens. By the 1930s he was not only one of the highest paid actors in Hollywood but married to one of the richest women in the world, Woolworth dime store heiress Barbara Hutton. (Inevitably, the press dubbed them Cash & Cary. The marriage lasted three years.) Frugal habits can die hard, though, and in Grant’s case they seem to have been immortal.

Among other tales, he supposedly marked the milk bottles in his refrigerator to keep servants from helping themselves to a swig, billed his houseguests for laundry and other expenses, and charged 25 cents apiece for autographs—pocketing the money while claiming it would go to charity, according to biographer Marc Eliot. Grant himself happily admitted to the gossip that he liked to cut off and save the buttons from his worn-out shirts: “It seemed like a sensible thing to do,” he told a reporter.

In any case, it all seems have paid off. Late in Grant’s long career, Time magazine reported that the actor still had “virtually every nickel he has ever earned.” Not to mention a lot of buttons.

(1834 – 1916)

An investing genius who built a fortune worth more than $2 billion in today’s dollars, Hetty Green was considered the richest woman in the U.S. in her day. But she was even better known as the Witch of Wall Street, a nickname that fit both her icy-hearted business practices and her habit of dressing entirely in black. Green was also a notorious skinflint.

When she needed to see a doctor, she would don the shabbiest of her black garb and head to a free clinic, signing in under a false name to avoid paying. A widely circulated story held that her son lost a leg because Green was unwilling to pay for proper treatment, although biographer Charles Slack says that seems over the top even for her.

Despite her huge real-estate holdings in New York, Boston, Chicago, and St. Louis, Green lived in a series of cheap rental apartments and rooming houses. In restaurants, she was known to haggle with waiters over the menu prices before ordering some inexpensive item. But she preferred to avoid restaurants altogether and often carried a bucket of dry oatmeal, which she would mix with water and heat on the nearest radiator.

(1920 – 2007)

The New York hotel baroness popularly known as the Queen of Mean might just as well have been called the Princess of Penuriousness. Once quoted as saying, “We don't pay taxes. Only the little people pay taxes,” she seems to have applied that philosophy to bills in general. At one time she was being sued by eight separate contractors she’d stiffed on work at her Greenwich, Conn., mansion.

Helmsley reportedly demanded kickbacks from suppliers, cheated on her sales and income taxes, and billed any personal expenses she could think of to her hotels. She eventually crossed so many lines and antagonized so many people that she found herself on trial for tax evasion and spent 18 months in the slammer.

The developer Donald Trump, who’d had ample experience dealing with Helmsley, was among those who found little cause for sympathy. “I can feel sorry for my worst enemy, but I can’t feel sorry for Leona Helmsley,” he was quoted as saying. “She deserves whatever she gets.”

Helmsley died in 2007 and, in a rare act of generosity, left $12 million to her dog.

(1889 – 1974)

Another billionaire oilman, H.L. Hunt was often reported to be a model for J.R. Ewing, the scheming patriarch on the television series Dallas. Unlike J.R., however, H.L. was renowned for his rumpled frugality—buying his suits off the rack, brown-bagging his lunch, cutting his own hair, and driving himself to work in an old Plymouth. He reportedly parked blocks from his office to avoid a 50-cent parking fee and enjoyed a reputation as a meager tipper.

He outdid even J.R., however, in the messiness of his private life, which Texas Monthly later characterized as “one of the most scandalous familial relationships in American history.” As the magazine explained it, “H.L. had three families, and two of them were a secret, at least for a while. Over one eight-year period in the late twenties and early thirties, he had seven children by two wives, none of whom knew of the others’ existence. As if that weren’t enough, he later had a third secret family.”

Hunt himself once observed that, “a millionaire who throws his money around is stupid.” Especially if he has three households to support.

(1917 – 1963)

Despite his image as a rich, carefree playboy, our 35th president was also a serious tightwad. Kennedy had no shortage of cash—his father had given him a trust fund worth $170 million in today’s dollars—but he rarely, if ever, carried any. Instead he allowed his friends, flunkies, Secret Service agents, and even dates to pick up the tab wherever he went. His frugality continued into the presidency, where he and First Lady Jacqueline Kennedy reportedly clashed over her spending on clothes and even the White House grocery bill.

Barely two months after his assassination, the government rushed out a half-dollar coin bearing his likeness, an unusual honor for someone to whom cash meant so little.

A man of many contradictions, Kennedy may also have been among the most generous of presidents in at least one respect: He reportedly donated his entire salary to charity.

(1906 to 1975)

Jacqueline Bouvier Kennedy may have thought her days of living with a cheapskate were over when she married the billionaire shipping tycoon Aristotle Onassis. But au contraire.

While Onassis seems to have been generous with his new bride—she went on a clothes-shopping spree that caused one magazine to label her “the retailer’s best friend"—he also had some habits that must have made her wonder what she’d gotten herself into.

Biographer Stephen Birmingham tells of Onassis making a surprise visit to the crew’s kitchen aboard his yacht: “Yanking the lids from the garbage pails, [he] plunged his hands deep into their unlovely contents. Coming up with handfuls of uneaten spaghetti, he cried angrily, ‘Why has this food been thrown away?’”

Onassis was not only renowned for his miserly tips but for avoiding the practice whenever possible. For example, he refused to wear a coat when he went to nightclubs, even in the dead of winter. “Since I am known as a rich person, I feel I have to tip at least $5 each time I check my coat,” he once explained. “On top of that, I would have to wear a very expensive coat, and it would have to be insured.”

(1894 – 1972; 1896 – 1986)

When King Edward VIII famously gave up the British throne in 1936 to marry American divorcée Wallis Simpson, he didn’t give up much else. Though demoted to Duke of Windsor, he still possessed a royal fortune; estimates range from $80 million to $250 million in today’s dollars. Even so, he would soon earn a reputation as a serious shilling-pincher.

Windsor was notorious for rarely, if ever, picking up a dinner check, preferring instead to wait his guests out. According to biographers J. Bryan III and Charles J. V. Murphy, “His dillydallying tactics included staring into the middle distance, whistling a light tune, and drumming his fingers on the table, until one of the guests finally picked up the bill and paid it, as his only hope of getting home before dawn.”

The duke and duchess had homes around the world but spent much of their time traveling, typically at highly discounted prices. Their favorite ocean liner became the S.S. United States, which provided a three-room suite—one room for the duke, one for the duchess, and one for their pugs—at about 70% off the fare for commoners. (In return the duke would hold a shipboard press conference at the end of the voyage, and he and the Mrs. would occasionally show up for bingo.)

As for the duchess, she seems to have been her husband’s willing co-conspirator in getting others to pick up the tab, which left more money to indulge her expensive tastes in clothes and jewelry. The bills for her clothing alone routinely topped $800,000 a year in today’s dollars.