The Most Scandalous Affairs In Pop Culture History

The world was rocked by each and every one.
Loading the player...

Over the years, we’ve seen several celebrity couples fall in love and get married. However, if Hollywood has taught us anything, it’s that relationships don’t always mean happily ever after.

So, although for many Tinseltown brings fame, fortune and long hours on set have proven to provoke all kinds of scandals throughout the years—and we’d be lying if we said weren’t often fascinated by the compelling details of celebrity relationship breakdowns.

From Marilyn Monroe and John F. Kennedy, to David Beckham and Rebecca Loos, there’s been a fair amount of outrageous affairs in pop culture history—which have often ended in bitter divorce and ignominy.

Here, the most scandalous celebrity affairs which shook the entertainment industry.

Ashton Kutcher, Sara Leal and Demi Moore

Ashton Kutcher and Demi Moore had been married for six years when administrative assistant Sara Leal alleged she had intimate relations with Kutcher in an interview with Us Weekly.

According to Moore’s 2019 memoir Inside Out, she found out about the alleged cheating via Google alert, prompting her to confront Kutcher who, in her words, “admitted it right away”. The scandal was the catalyst for the breakdown of their marriage, with the pair finalising their divorce in 2013.

Kutcher has never directly addressed the scandal, except for a 2017 speech he gave when accepting a ‘Role Model Award For Good Character’. “I’m also probably the first person to get this award for character who had, like, his name splashed across every gossip magazine as an adulterer like five years ago,” he said, according to PEOPLE.


Marilyn Monroe and John F. Kennedy

Rumours first circulated that the two had an affair when the President was married to Jackie Kennedy, which were further spurred by Marilyn Monroe’s sultry performance of “Happy Birthday” to the president. It was also rumoured that Monroe had an affair with JFK’s brother, Attorney General Robert F. Kennedy.

john f kennedy

David Beckham and Rebecca Loos

In 2004, David Beckham’s personal assistant Rebecca Loos claimed they had sexual relations, referring to herself as the soccer player’s “second wife.”

This led Beckham to issue a statement whereby he said “the simple truth is that I am very happily married. I have a wonderful wife and two very special kids. There is nothing any third party can do to change these facts.” Although causing a strain in his relationship with former Spice Girl Victoria Beckham, the fashion designer told [V Magazine] that “there have been bumps along the road. But the fact is we’ve come out of everything we’ve been through stronger and happier.”

Loos went on to appear in TV shows including Celebrity Love Island and The Farm.

david beckham

Elizabeth Taylor and Eddie Fisher

One of the biggest scandals of the 1950s was the affair between Elizabeth Taylor and Eddie Fisher. Fisher, who was married to Debbie Reynolds at the time, comforted Taylor when her husband Mike Todd died—and later fell for the actress. He divorced Reynolds and married Taylor in 1959. However, just five years later Taylor divorced Fisher for her Cleopatra co-star Richard Burton. They were married in 1964.

elizabth taylor

Brad Pitt and Angelina Jolie

Brad Pitt was married to Jennifer Aniston when sparks flew on set while filming Mr. & Mrs. Smith with co-star Angelina Jolie. Aniston filed for divorce in 2005, and Jolie later caused a stir in 2008, when she said in an interview that she that she and Pitt were looking forward to their children seeing Mr. & Mrs Smith one day: “Not a lot of people get to see a movie where their parents fell in love.” The couple split in 2016 after a 10-year relationship.


Billy Bob Thornton, Laura Dern and Angelina Jolie

Before her affair with Brad Pitt, Angelina Jolie was involved in a celebrity love triangle of sorts with Big Little Lies star Laura Dern and actor Billy Bob Thornton (who Jolie later married). Dern and Thornton had been together for around two years in the late ’90s when things between them ended rather abruptly, with Thornton reportedly leaving Dern to marry Jolie before properly ending things with the Marriage Story actress.

In a 2000 interview with the now-defunct Talk magazine, Dern explained that Thornton left her while she was away for work.

“I left our home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again. It’s like a sudden death. For no one has there been any closure or clarity,” she said.

laura dern

Humphrey Bogart and Lauren Bacall

Humphrey Bogart met Lauren Bacall while filming To Have and Have Not in 1944. He was 44 and married at the time, and she was just 19. Despite their 25-year age gap, a romance began between them.

When their director Howard Hawks (who reportedly also fancied Bacall) caught wind of their relationship, he reportedly tried to put an end to their liaison by telling the actress that Bogart would dump her by the end of filming, and allegedly even threatened to destroy her career, bluffing that he would send her to the “lowest” studios in Hollywood. Despite Hawks’ meddling, Bogart and Bacall’s relationship continued, and the pair wed in 1945. They went on to have two children together and remained married until Bogart passed away in 1957.

billy bob

Prince Charles, Camilla Parker Bowles and Princess Diana

It was the affair that shook the monarchy and sparked tabloid headlines around the world. Prince Charles and Princess Diana, who wed in 1981, had been married for five years when he began secretly seeing his former girlfriend, Camilla, who he dated prior to his marriage. Camilla was also married at the time.

In 1992, the late princess reportedly admitted to confronting Camilla at a 1989 party, where she said:

“I know what’s going on between you and Charles and I just want you to know that. She said to me: ‘You’ve got everything you ever wanted. You’ve got all the men in the world fall in love with you and you’ve got two beautiful children, what more do you want?’ So I said, ‘I want my husband.'”

It was not until 1994, that Prince Charles gave a bombshell interview for a TV documentary that the rumours were officially confirmed, with the royal admitting that he’d stayed faithful to Diana, “until it became irretrievably broken down, us both having tried.”


Princess Diana, James Hewitt and Prince Charles

James Hewitt, a polo player and British cavalry officer, first met Princess Diana at a party in 1986, where he apparently offered to help get over her fear of horses. Eventually, horse riding lessons led to an affair. Diana admitted to the affair with Hewitt in a 1995 interview, saying: “Yes, I adored him. Yes, I was in love with him. But I was very let down.”

Hewitt also spoke about their five-year liaison to writer Anna Pasternak, who penned the book Princess In Love following his stories. Speculation has long been rife that James is Prince Harry’s real father as the pair do share a resemblance, but the polo player has stated that there’s “no possibility whatsoever” of that being the case, as Harry was born in 1984.

“I have never encouraged these comparisons and although I was with Diana for a long time, I must state once and for all that I’m not Harry’s father,” he said. “When I met Diana, he was already a toddler.”

The pair were forced apart when he was deployed to serve in the Gulf War, with their affair officially ending after it was exposed in the media.

james charles

Hugh Grant and Elizabeth Hurley

In 1995, Grant was arrested in Los Angeles for misdemeanour lewd conduct in a public place, with Hollywood prostitute Divine Brown—he was in a relationship with Hurley at the time. The actor pleaded no contest and paid a fine. Some days later he appeared on The Tonight Show, where he said, “I did a bad thing,” which saved his career and saw public forgiveness. Although Hurley forgave Grant initially, they later split in 2000.


Frank Sinatra and Ava Gardner

Considered one of the ’40s and ’50s most infamous Hollywood couples, jazz crooner Frank Sinatra began dating actress Ava Gardner while still married to his wife Nancy, with whom he shared three children. He eventually left Nancy for Gardner, who he married in 1951 (pictured here on their wedding day). But that wasn’t the end of the drama. Sinatra’s affairs (of which he had many throughout his life) did not end there. The singer was also unfaithful to Gardner in their marriage, and the ultimately divorced in 1957.


Jude Law and Sienna Miller

In 2005, Jude Law admitted that he had cheated on his fiancée Sienna Miller with his children’s nanny. Law soon made a public apology, which stated, “I’m deeply ashamed and upset that I’ve hurt Sienna.”

The nanny, Daisy Wright, did a tell-all interview where she said that Law was a “great lover.” Law and Miller soon split. However, years later Miller was photographed topless and kissing actor Balthazar Getty, a married man with four children.

In a new interview in December 2020 with The Daily Beast, the actress reflected on her split Law over a decade ago. 

“It was really hard,” she said of the scandal. “And the other thing was, it was at the height of all that paparazzi madness, and in London where there was an epidemic of bad behaviour. They knew where I would be every night.”

“That was one of the most challenging moments I hope I’ll ever have to experience. Because with that level of public heartbreak, to have to get out of a bed let alone stand in front of 800 people every night, it’s just the last thing you want to do,” added the actress, who was starring in a production of the Shakespeare play As You Like It at the time.

Miller went on to state that she blocked out most of that time period from her memory. “There’s a whole six weeks of that experience that I don’t remember. I have no recollection of it,” she said.

“People who came to see me said we had dinner, and I don’t remember,” the actress added. “I was in so much shock over it all. And I’d really just begun. I was only 23. But if you get through that, you feel like you can get through anything.”

sienna miller

Sophia Loren and Cary Grant

The old Hollywood heartthrob first shared the silver screen with the Italian siren in 1958’s Houseboat. Cary Grant’s wife at the time, actress Betsy Drake, wrote the original script for Houseboat, in which she was cast alongside her husband in the film. As the story goes, after Grant, who was 54 at the time, and Loren, 23, commenced their affair, Grant had a new script commissioned to cut his wife out of the role and replaced her with Loren. Drake never received credit for writing the movie, and Loren eventually left Grant to marry Carlo Ponti. In 2014, the Italian actress admitted to the affair, which she insists was “unconsummated”.


Arnold Schwarzenegger and Maria Shriver

Danish actress Brigitte Nielsen revealed she and Schwarzenegger had an affair while he was married to Maria Shriver, in a memoir published in 2011. Schwarzenegger later admitted to the affair, which prompted the end of his 25-year marriage to the Kennedy family daughter and newswoman.


Sandra Bullock and Jesse James

Several years after Sandra Bullock married Jesse James, a motorcycle customiser, many women claimed to have affairs with James during his relationship with Bullock. Michelle McGee, a dancer, revealed that she had sex with James on the couch in his office behind Bullock’s back. As a result of the rumours, James soon confessed and issued a public apology asking for forgiveness. Bullock filed for divorce in April, 2010 and then adopted a baby boy as a single mother.


Kristen Stewart, Rupert Sanders and Robert Pattinson

In July 2012, Kristen Stewart made headlines for cheating on her boyfriend and co-star Robert Pattinson with her Snow White and the Huntsman director, Rupert Sanders—he was married at the time. Stewart later publicly apologised to Pattinson and they resumed their relationship, however, later that year split. Stewart is now dating screenwriter Dylan Meyer.


David Letterman and Regina Lasko

In 2009, six months after marrying longtime girlfriend Regina Lasko, The Late Show host admitted to being involved in a sex scandal. He admitted on the show that he “had sex with women who work for me on this show.” He later spoke to Oprah about dealing with the fallout from cheating on his wife and mother of his son: “I’m still trying to fix it.”

david letterman

Elin Nordegren and Tiger Woods

In 2009, the National Enquirer reported that Woods cheated on his wife with nightclub manager Rachel Uchitel. Rumours soon emerged that Nordegren attacked Woods with a golf club, and he responded by naming the issue a “private matter.” More than 12 women soon claimed to have flings with Woods, sharing texts and voice mails as proof, which finally led Woods to admit to infidelity and apologise. As a result of this, Woods lost several endorsements, had to take a break from tournaments and divorced his wife in 2010.

tiger woods

Related stories