Celebs Who Ruined Their Reputations In Hollywood By Cheating More Than Once

Let's face it, Hollywood is often a breeding ground for debauchery, and some of the industry's most buzzed-about stars have had their dirty laundry aired out for the world to judge. Since its inception, cheating scandals have become run-of-the-mill in Tinseltown, though some celebrities have completely destroyed their reputations with their personal indiscretions. Looking at these famous figures in the same way can be difficult once their illicit relationships have been exposed. Fans often waste no time expressing their disappointment.

While some celebrities learn from their mistakes and attempt to repair their romances, others just can't seem to help themselves and become repeat offenders when it comes to cheating. Even back in the golden age of Hollywood, no affair ever truly stayed hidden, and shutterbugs lurked at every corner in hopes of exposing a juicy scandal. Screen siren Elizabeth Taylor was married a stunning number of times and was infamously vilified for one of her globe-trotting affairs in the '60s. Media scrutiny has only intensified in the decades since.

Nowadays, celebrities are constantly under a microscope thanks to the internet. When a star strays from their romantic partner (especially more than once), there is no place for them to hide in the digital age. 

Charlie Sheen is no stranger to chaos and controversy. For example, the acting veteran famously went on an explosive tirade in 2011 after getting fired from his hit sitcom "Two and a Half Men." Aside from his past public outbursts, Sheen's love life has proved just as messy. He was married to his first wife Donna Peele from 1995 to 1996, though their union was ultimately short-lived. Peele filed for divorce when Sheen's name appeared on an escort service list for Hollywood madam Heidi Fleiss, which revealed he had spent more than $53,000 on call girls.

Sheen was married to fellow actor Denise Richards from 2002 to 2006.His addiction struggles plagued the couple, as did his alleged extramarital affairs. The couple's divorce proceedings were constantly in the tabloids. Richards was six months pregnant at the time, and she claimed in her sworn declaration that Sheen was addicted to prostitutes, pornography, and gambling (via The Smoking Gun). Their divorce was finalized in 2006, and Sheen and Richards had many messy moments in the ensuing years.

Sheen moved on and married his third wife Brooke Mueller in 2008. She too accused him of being unfaithful during their three-year marriage, and the TV star had been caught with escort Angelina Tracy in 2010. The couple divorced the following year. Though Sheen's infidelities didn't completely destroy his Hollywood reputation, they sure didn't do him any favors, and they deeply affected his public persona. 

Elizabeth Taylor was known as a cinema vixen and one of Tinseltown's most revered performers, but her love life was constant tabloid fodder that often overshadowed her many professional achievements. Taylor was married eight times to seven different men throughout her life, and in 1958, she had a high-profile affair with the singer Eddie Fisher following the death of her husband Mike Todd. Their liaison was one of old Hollywood's most scandalous affairs and tarnished Taylor's reputation, in part because Fisher had been married to her close friend Debbie Reynolds.

Taylor and Fisher eventually married in 1959, just three hours after his divorce from Reynolds was finalized, and she was branded a "home-wrecker" by the media. She later claimed she never loved Fisher and had only been with him out of grief. "I never loved Eddie. I liked him. I felt sorry for him. And I liked talking [to him]. But he was not Mike," she said in the documentary "Elizabeth Taylor: The Lost Tapes" (via People).

While filming the 1962 classic "Cleopatra," Taylor famously fell in love with her co-star Richard Burton, and the pair was brazenly open about their affair. They were famously photographed by paparazzi on a yacht in Ischia and attracted intense public scrutiny. The Vatican even condemned them for "erotic vagrancy." As Taylor later revealed in "The Lost Tapes," "My father called me a w***e" in response to her illicit relationship with Burton (via Mirror). 

"That '70s Show" superstar Ashton Kutcher's unexpected romance with leading lady Demi Moore initially caught the world by surprise in 2003, as did their subsequent nuptials in 2005. The two made a love connection when they met at a dinner with mutual friends. At the time, Kutcher was 25 and Moore 40, and the couple's age gap sparked media fascination. "I don't know, it's so silly," Moore told ABC News of the public's intense interest in their age difference.

"I was a 40-year-old who had a big life. And Ashton's adult life was just beginning — I didn't see all that because I was inside of it." After six years of marriage, rumors of Kutcher's alleged infidelity plagued the couple. Moore officially announced their separation in 2011, and their divorce was finalized in 2013. Moore provided insight into their split in her memoir "Inside Out," revealing how she even agreed to Kutcher's desire to open up their marriage intimately; this decision allegedly led to him further straying romantically.

"Because we had brought in a third party into our relationship, Ashton said, that blurred the lines and, to some extent, justified what he's done," she wrote (via People). Kutcher was also accused of cheating on Moore with a 22-year-old woman on their sixth anniversary, an incident that further led to their demise. Kutcher's inappropriate antics messed with his Hollywood image, and he took a big step back from film and TV appearances following the public blowback to his divorce.

Actor and comedian extraordinaire Kevin Hart skyrocketed to fame in 2009 after releasing his stand-up special "I'm a Grown Little Man," which shared stories about his two children (he now has four) and wife Torrei Skipper Hart. Hart and Torrei were married from 2003 to 2011, citing irreconcilable differences in 2010. He admitted to cheating on Torrei in his stand-up show "Kevin Hart: Let Me Explain" in 2013.

"I cheated. Am I ashamed of it? No, I'm not," he told the audience (via People). "Do I wish I could take it back? No, I don't. Let me tell you why. You can't evolve as a man if you don't make a mistake. The only way that you can be perfect is to not f*** up. I did it, I f***ed up. Don't cheat!" Hart must not have taken his own advice because just a few years later, he found himself in yet another cheating scandal. Following his divorce from Torrei, Hart began a romance with Eniko Parrish, whom he married in 2016.

Hart made headlines in 2017 when he was accused of cheating on Parrish while she was pregnant with their son. Following an alleged extortion attempt, he admitted to his affair in an emotional video on Instagram. He apologized to Parrish and his children for his indiscretions, and the couple eventually reconciled, though Hart's everyman, family-friendly reputation was shattered, and he left fans disappointed. 

Action legend-turned-politician Arnold Schwarzenegger and journalist Maria Shriver first met in 1977 at a tennis tournament. The couple struck up a romance and married in 1986. He was living with Shriver when he had an affair with his "Red Sonja" co-star Brigitte Nielsen in 1985, which the actor revealed in his 2012 memoir "Total Recall: My Unbelievably True Life Story." In an interview with "60 Minutes," Schwarzenegger was questioned about whether he felt bad about his fling with Nielsen.

"Actually, you know, I did feel bad about it," Schwarzenegger said (via Entertainment Weekly). "But all of my different things — they were mistakes, and you know, my failure. My screw-ups." The shocking confession came on the heels of Schwarzenegger admitting to an affair with his housekeeper Mildred Baena, which resulted in the birth of their son Joseph in 1997. The couple continued to employ Baena until 2011. 

Schwarzenegger's infidelities severely impacted his standing as a respected public figure. Shriver separated from the movie star in 2011, and the couple divorced after 25 years of marriage. Schwarzenegger remained remorseful about his actions, though the public was outraged. "Everyone had to suffer. Maria had to suffer. The kids had to suffer. Joseph. His mother. Everyone," He said in the Netflix docuseries "Arnold" (via People). "I am going to have to live with it the rest of my life. People will remember my successes and they will also remember my failures. This is a major failure." 

Claire Danes became a household name when she was just a teenager after headlining the '90s sensation "My So-Called Life," a series for which she won a Golden Globe Award and the adoration of millions. In 1997, she began a relationship with musician Ben Lee, and the two remained together until 2003. Danes left Lee to pursue her blossoming romance with Billy Crudup, whom she fell for while filming "Stage Beauty."

Their relationship shocked the world because at the time, Crudup was with Mary-Louise Parker, who was seven months pregnant when he broke up with her. Naturally, a media firestorm ensued given the timing of their romance, and Parker reportedly banned him from the hospital room during the birth of their son William. Danes and Crudup were together until 2006, during which the press largely vilified her alone despite the role both stars played in their affair.

"That was a scary thing," Danes told Howard Stern (via Vanity Fair). "That was really hard. I didn't know how to not do that. I was just in love with him. And needed to explore that, and I was 24 ... I didn't quite know what those consequences would be ... But it's OK ... I went through it." Ironically, rumors spread that Danes left Crudup to be with her "Evening" co-star Hugh Dancy because the two began a relationship shortly after their breakup. Danes remained mum, but the timing was suspicious and raised eyebrows. 

TV actor Eddie Cibrian is perhaps best known for his roles in the soap operas "The Young and the Restless" and "Sunset Beach," and in 2001, he married reality TV star Brandi Glanville. Together, the couple welcomed two sons during their nine-year marriage. In 2006, Cibrian had a fling with "Vanderpump Rules" star Scheana Shay and later made headlines when his affair with his "Northern Lights" co-star, singer LeAnn Rimes, came to light in 2009.

Cibrian and Rimes' romance led them to divorce their respective partners, Glanville and Dean Sheremet, and the couple wed in 2011 despite the ire of the public. "I take responsibility for everything I've done. I hate that people got hurt, but I don't regret the outcome," Rimes told People about the origins of their relationship. "The truth is that we're human beings. We make mistakes and we learn from them, but we're human. We fell in love."

The couple faced intense backlash because of the affair, and both of their careers took massive hits as a result. Cibrian's TV and film opportunities became fewer and farther between, and Rimes' album "Lady & Gentlemen" (her first following their affair) failed to match the success of its predecessor "Family," charting at No. 32 in comparison to No. 4 on the U.S. Billboard 200. Neither star was able to achieve the fame they previously enjoyed prior to their scandalous affair. 

Oscar-nominee Ralph Fiennes established himself as one of the industry's most dynamic actors thanks to performances in acclaimed films like "Schindler's List," "The English Patient," and the blockbuster "Harry Potter" series. Despite being a force on the screen, Fiennes' personal life garnered less-than-desirable attention. The English star married Alex Kingston in 1993 after dating for a decade, but their relationship came to a screeching halt following his affair with Francesca Annis, who was 18 years his senior.

Fiennes and Annis met while starring in a production of "Hamlet" in 1995, and their illicit romance sent shockwaves through the industry, leading to Fiennes' divorce from Kingston in 1997. Kingston has spoken out about the emotional trauma she experienced and how she had even become suicidal during that harrowing time. "I can't imagine being that person at all," she told the London Evening Standard (via "Today"). "You don't know where life is going to take you. You think you know and then all of a sudden you realize it's all completely wrong."

The actor and Annis broke up in 2006, when Fiennes allegedly strayed once again and had an affair with singer Cornelia Crișan. In fact, Crisan also accused Fiennes of seeing someone else during their own affair. "'He was a cheat," she told The Mail (via The Standard). "Playing hot and cold with a woman gave something to his ego. Knowing that there was someone maybe crying for him, maybe suffering, made him feel better about himself."  

Hollywood triple threat Justin Timberlake is known for topping the charts with hit songs like "Cry Me a River" and "SexyBack," though the Grammy winner's reputation was dragged through the coals over his romantic transgressions. From 1999 to 2002, Timberlake was in a high-profile relationship with pop princess Britney Spears, and in her memoir "The Woman in Me," she accused him of having a wandering eye. "There were a couple of times during our relationship when I knew Justin had cheated on me," she wrote (via Business Insider).

"Especially because I was so infatuated and so in love, I let it go, even though the tabloids seemed determined to rub my face in it." This wasn't the first time Timberlake had been accused of cheating. He was allegedly also unfaithful to Cameron Diaz with Playboy model Zoe Gregory. Fast-forward to 2019, and the singer once again found himself in hot water after photos began circulating of him holding hands with his "Palmer" co-star Alisha Wainwright.

"A few weeks ago I displayed a strong lapse in judgment — but let me be clear — nothing happened between me and my co-star," Timberlake wrote in a since-deleted Instagram post (via HuffPost). "I drank way too much that night and I regret my behavior. I should have known better." He apologized to his wife Jessica Biel, though the internet relentlessly mocked him for his behavior in the aftermath of his cheating scandal.

Breaking up with America's sweetheart is never easy, and Ryan Phillippe learned this lesson the hard way after he divorced his longtime love Reese Witherspoon in 2007. The two met in 1997 at her 21st birthday party, and the couple shared the screen in "Cruel Intentions" in 1999. They tied the knot that same year, when Witherspoon was six months pregnant. They swiftly became a Hollywood gold couple, and Phillippe supported Witherspoon when she won an Oscar in 2006 for her role in "Walk the Line."

The pair's love story came to a shocking end shortly afterward. They announced their separation later that year, after seven years of marriage, and Witherspoon cited irreconcilable differences. Soon after, rumors swirled that Phillippe had cheated on Witherspoon with Abbie Cornish, his co-star in the film "Stop Loss," and also had been involved with two other women during production. Though he denied the rumors, Phillippe and Cornish began publicly dating in 2006, further fueling the allegations.

In another twist, Phillippe and Cornish split in 2010 amid reports that he had been getting cozy with other women; when asked about the infidelity rumors, Cornish's publicist replied, "No comment" (via People). In an interview with Howard Stern, a fired-up Phillippe voiced his frustration over the endless media scrutiny. "I've been dumped on in the press for relationship stuff since Reese and I divorced. ... I'm tired of getting s*** on. I don't feel like I deserve it," he said (via Us Weekly).

Dean McDermott is largely known as the ex-husband of "Beverly Hills, 90210" alum Tori Spelling, though before his romance with the star, he had appeared in the 2003 Kevin Costner film "Open Range" and shows like "Due South" and "Earth: Final Conflict." McDermott had been married to his first wife Mary Jo Eustace since 1993, when he met Spelling on the set of their Lifetime movie "Mind Over Murder," and the two began an affair in 2005.

Spelling was married to Charlie Shanian at the time, and she confessed in her memoir "sTori Telling" that their attraction was instant. "It was love at first sight. I fell so hard ... Then I noticed he had a wedding ring. And — oh, yeah — I had a husband too," she wrote (via Us Weekly). McDermott and Spelling married less than a month after his divorce from Eustace was finalized in 2006. Alas, their wedded bliss did not last, and McDermott confessed to cheating on Spelling with Emily Goodhand in 2013.

Though the couple eventually worked through the infidelity, they were plagued by trust issues and constant media ridicule, separating in 2023. Spelling filed for divorce the following year and eventually took to her podcast "misSPELLINg" in November 2025 to describe her divorce from McDermott in an unexpected way. "I am officially divorced ... I gotta say, you guys, this is something never said — this was one of the easiest divorces in Hollywood. You can quote me there. Screw it, take 'Hollywood' out."