Top 10 Badass Mistresses

They say that behind every powerful man is an even more powerful woman. But throughout history, not every woman standing behind her man was his wife. Some mistresses were confidantes or muses, some became liabilities. But all of them left their mark. Meet the top 10 most badass mistresses in history.

10. Ashley Dupré

Ashley Dupre

Top 10 Badass Mistresses

In 2008 Ashley was 22 years old and working as a high-end call girl in New York when she took the train to Washington DC to meet a new client. He turned out to be New York governor Eliot Spitzer, and when his predilection for prostitutes became public because of an unrelated FBI investigation, he was forced to resign. Dupre, who knew Spitzer as “Client 9” was arrested but never prosecuted and turned her moment in the spotlight as “The Most Famous Hooker in America” into a lucrative media career, appearing on several reality shows, magazine spreads, and as a weekly sex columnist for The New York Post newspaper. In addition to being a columnist for the New York Post, she’s starred on a reality series called Famous Food.  Dupré came in third; first and second prizes were given a partnership stake in the Lemon Basket.  She is also a professional singer. Jerry Cooper, a musician she was living with, heard her singing Aretha Franklin’s “Respect” in the shower.

9. Marion Davies

Marion Davies

Top Ten Badass Mistresses

Silent film actress Davies met William Randolph Hearst, publisher of Hearst magazines and one of the richest, most powerful men in the world when he backed one of her films in 1918. She started getting starring roles and became hugely famous soon after their affair began and by the mid-1920s, their relationship was an open secret in Hollywood. Hearst built San Simeon, the largest privately owned house in the world for Davies. The couple hosted Hollywood stars, politicians and other luminaries for lavish weekend parties that became legendary. Davies and Hearst never married because Hearst’s wife’s divorce settlement demands were too high, but he left half of his fortune to Davies when he died. She married a longtime friend 10 weeks later.

8. Gennifer Flowers

Gennfer Flowers

Top 10 Badass Mistresses

Model and actress Flowers claimed very loudly and very publicly that she had had an affair with then presidential candidate Bill Clinton in 1992. Clinton vehemently denied the affair but rumors were so persistent that he felt compelled to appear with his wife Hillary on 60 Minutes to deny them. By 1998, in the wake of other sexual scandals, Clinton was forced to admit the affair, but not before Flowers had successfully sued members of his White House staff for defamation of character, posed for Penthouse Magazine, and written a memoir about the affair. She has since said that the publicity surrounding her relationship with the 42nd president of the United States netted her about $500,000. When George Stephanopoulos and James Carville tried to defame her character, she sued them for slander, claiming that they created a phony campaign to discredit her. Judicial Watch represented her in the matter.  What a Badass!

7. Lola Montez

Lola Montez

Top Ten Badass Mistresses

Montez, whose real name was Eliza Rosanna Gilbert, was born in Ireland in 1821. Not much is known about her early life, except that as a teenager she became an actress on the European stage. During one of her performances, the beautiful Montez caught the eye of King Ludwig of Bavaria, who made her his mistress. Almost immediately, she became the aging king’s political confidante and she was eventually able to take the reigns of power in the kingdom. Lola ruled Bavaria for over a year, until a coup largely caused by her iron-fisted policies forced Ludwig to abdicate and Lola to flee. She spent the rest of her life as an actress, racking up 2 bigamist marriages and a murder charge along the way. She died in New York at the age of 40.

6. Wallis Simpson

Wallis Simpson

Top 10 Badass Mistresses

It’s not often that mistresses of the rich and famous wind up marrying their paramours, but American divorcee Wallis Simpson did just that…and almost brought down the British monarchy in the process. In 1934, Edward, Prince of Wales became besotted with Simpson and the 2 began an affair, despite the fact that the prince was expected to find a suitable wife. In the eyes of the British monarchy a newly divorced American did not fit the bill. When he became king in 1936, Edward wavered about ending his love affair but finally decided that he would rather have his mistress than the throne of England. On December 11, 1936 he took to the radio to abdicate, announcing that he couldn’t be king “without the help of the woman I love”. England’s monarchy was thrown into a tailspin, but Edward and Wallis’ marriage lasted for 35 years, until Edward’s death in 1972. The Duchess of Windsor died on April 24, 1986. She was buried next to her husband in the Royal Burial Ground, as “Wallis, Duchess of Windsor”.

Throughout her lifetime, Wallis was plagued by rumors of other lovers. The gay American star Jimmy Donahue claimed to have had an affair with the Duchess in the 1950s, but Donahue was known for his inventive pranks and rumor spreading ways. Although she never had children,  rumors were floating around about her being pregnancy and having abortions, most notably involving Count Ciano in China. However, there’s no solid evidence to prove this.

5. Anne Boleyn

Anne Boleyn

Top Ten Rebellious Mistresses

Until 1534 the official religion of Britain was Catholicism. In that year, King Henry the Eighth created a new religion so that he could marry his mistress, Anne Boleyn. Boleyn was a lady-in-waiting to Henry’s wife, Queen Catherine, and Henry became obsessed with the idea that Anne could produce the male heir that his wife had not. When the Catholic church refused to grant an annulment of Henry’s marriage he left the church and took all of England with him, creating The Church of England….which grants divorces. Anne and Henry married but the king soon became suspicious of other affairs and had Anne executed. Henry went on to marry 4 more times and never did father a son who lived to become king, but he and Anne were parents to perhaps the most famous queen in history: Elizabeth I. Her sister Mary Boleyn was also a lover of King Henry, but that is a topic of the next discussion.

4. Elizabeth Taylor


Top 10 Coolest Mistresses

The legendary actress was known for her beauty, her glamor, her violet eyes and her 8 marriages. But she was also a notorious mistress. Twice. In 1959, Taylor began a torrid romance with her recently-deceased husband’s best friend, singer Eddie Fisher. Fisher was married to sugary-sweet actress Debbie Reynolds and when news of the affair became public, Taylor was nearly blacklisted in Hollywood and abandoned by fans. In 1964, long after she had divorced Fisher, Elizabeth became involved with actor Richard Burton. Both were married and the movie-going public was outraged. The relationship garnered so much attention that the Vatican condemned it as “erotic vagrancy”. The 2 went on to marry each other, divorce, then remarry and divorce each other again. The Taylor/Burton relationship is considered by many to be one of the greatest romances of the 20th century.

3. Carrie Fulton Phillips

Carrie Fulton Phillips

Top 10 Badass Mistresses

Born in 1873, Phillips became the mistress of Ohio senator Warren G. Harding in 1906. Even after Harding became a U.S. Senator, the affair was kept secret. But when Harding became the Republican nominee for U.S. President, rumors began to circulate and Carrie, who by now had broken with Harding, made an unprecedented move. She blackmailed the Republican party, asking for hush money in return for not revealing hundreds of Harding’s love letters. The party, feeling it had no choice, paid her and Harding went on to become the 23rd president of the United States. Carrie Fulton Phillips died in 1960. At the time of her death she was still receiving a yearly ‘stipend’ from the Republican party.

2. Cleopatra


Top 10 Coolest Mistresses

Queen of Egypt, mistress of both Julius Caesar and his lieutenant Mark Antony, Cleopatra’s fame has not diminished in the 2000 years since she died. Though no record of what she looked like exists, her name has become synonymous with female beauty. She became a deity in Egypt after her suicide (supposedly by allowing herself to be bitten by a poisonous snake) and is still celebrated for her wit, political acumen and loyalty to Egypt. Cleopatra’s relationships with the 2 famous Romans were ones of necessity. Her loyalty was to Egypt and when her attempts to stop Roman invasion militarily failed she used the only means she had left: sex.

1. Marilyn Monroe

Marilyn Monroe

Top 10 Badass Mistresses

Considered the most desirable woman of her generation (or perhaps of any generation) actress Marilyn Monroe’s extra-marital relationships with both President John F. Kennedy and his Attorney General brother Bobby have been the subject of tabloid gossip for the past 50 years. Director of the FBI and Kennedy enemy J. Edgar Hoover knew about the affair and spent years trying unsuccessfully to get hard evidence that would ruin the Kennedy brothers’ political careers. Eventually Monroe’s fame and what was seen as her emotional instability became liabilities to the president and his brother, and the affairs were ended. She died at the age of 36 from an overdose of sleeping pills and rumors about the Kennedy brothers’ involvement in her death persist even to this day. Marilyn was only one of many of the Kennedy brothers’ mistresses, but she tops the list because of her fame, beauty, and influence on popular culture.

Honorable Mention: Catherine the Great


The Most Powerful Badass Mistresses

Shocking?! I bet. The Russian Empress was a mistress of many men throughout her “Golden Era” reign. When her husband Peter the Great failed to pay attention to her and cheated on her, she went on to find a man who would impregnate her. When she dethroned and assassinated her husband, she continued to take advantage of the everyday men for her own satisfaction. One of them was Count Grigory Grigoryevich Orlov who had fathered two of her children. She definitely is worth examining in this Top 10 List of Badass Mistresses.