15 Celebrities Who Were Caught Cheating...More Than Once
It shouldn't be that surprising. It's all over your newsfeed. Celebrities are allegedly cheating...again and again.
What's really shocking are the ones who were caught stepping out, not once — but TWICE, and sometimes even more!
Warner Bros Pictures / Via giphy.com
Here are 15 celebs who were involved in cheating scandals more than once.
1.Tiger Woods, one of the greatest golfers of all time, is also known as one of the biggest serial cheaters of all time.
In 2009, it was reported that Tiger Woods allegedly had a months-long affair with New York City nightclub host Rachel Uchitel. When discovered, his wife at the time, Elin Nordegren, attacked him. The following reports revealed porn stars, strippers, and escorts claiming to have had sex with Tiger. Tiger confessed to sleeping with 120 women while he was married.
2.Jesse James allegedly had multiple affairs while he was married to actor Sandra Bullock, and then followed that up by cheating on his fiancé, Kat Von D.
TV personality and famous mechanic Jesse James most famously cheated on his then-wife, Academy Award–winning actor Sandra Bullock. Just days after she won the Oscar for Best Actress in 2010, rumors of multiple affairs surfaced. After his marriage to Sandra, he dated L.A. Ink star Kat Von D and had to call off the engagement after it was revealed that he cheated on Kat with 19 women.
3.Throughout their complicated relationship, Tristan Thompson was caught cheating on Khloé Kardashian more than once.
In 2018, he was caught on camera allegedly cheating on Khloé at a hookah lounge only days before the birth of his daughter, True. He was allegedly caught cheating once again months later with Kylie Jenner's former bestie, Jordyn Woods. This wouldn't be the last of Thompson's highly publicized scandals — as everyone discovered recently, he fathered another baby while in the surrogacy process with Khloé for the birth of their second child together.
4.Chris Rock has been very candid in his comedy special about his serial cheating habits.
Comedian Chris Rock confessed to cheating on his wife, Malaak, with three different women. One of the women was allegedly identified as his I Think I Love My Wife (2007) costar Kerry Washington. The affair allegedly began around 2007 while Kerry was with actor David Moscow. When referring to the matter, Chris would jokingly promote his tour, saying, “It’s the alimony tour. I’ve got to make some money first."
5.Scott Disick allegedly wasn't the most faithful to the mother of his children, Kourtney Kardashian, on multiple occasions.
The former couple once broke up when pictures surfaced of Scott with his ex-girlfriend Chloe Bartoli in Monte Carlo. In 2017, Kim Kardashian also made a scene when she found a woman hiding in Scott's bathroom after the pair was caught hooking up in Dubai. Scott was caught another time flying a woman out during a family vacation in Costa Rica while trying to maintain a relationship with Kourtney. Technically, the on-again, off-again couple was not always "officially" together, but they continued to co-parent their children together during this time.
6.Rolling Stones frontman Mick Jagger reportedly had a robust history with different women throughout his decades-long music career.
Mick's relationship with model and actor Jerry Hall allegedly overlapped with his previous marriage to Bianca Pérez-Mora Macias. Years later, while his then-partner Melanie Hamrick was pregnant, he allegedly had an affair with a 23-year-old woman. He was also rumored to be linked to Kuwaiti American heiress Noor Alfallah during this time.
7.Lamar Odom admitted to cheating multiple times during his marriage to Khloé Kardashian.
Basketball player Lamar Odom opened up about having numerous affairs throughout his marriage to Khloé Kardashian. He confessed to being a sex addict and claimed that he has slept with "more than 2,000 women in his life." In his memoir, he explained that his marriage to Khloé began to spiral out of control. He "could not handle the lethal cocktail of the spotlight, addiction, a diminishing career, and infidelity."
8.Elizabeth Taylor was infamously rumored to have cheated on multiple husbands, including one who was initially married to her best friend, Debbie Reynolds.
According to the book Elizabeth Taylor: There Is Nothing Like a Dame, she had multiple high-profile affairs during her marriages to many famous men. The most publicized romance is when Elizabeth had an affair with Eddie Fisher. He was married to actor Debbie Reynolds when their relationship began. Elizabeth would go on to allegedly have an affair with her future husband, Richard Burton, while she was still married to Eddie.
9.Jude Law allegedly stepped out on the mother of his three children for his costar, only to have an affair with his family's nanny during the new relationship.
Amid a tumultuous divorce from a six-year marriage to Sadie Frost, Jude Law began a relationship with his Alfie (2004) costar Sienna Miller. In 2005, it was reported that Jude allegedly had an affair with Daisy Wright, the nanny of his three children with Sadie. Jude and Sienna attempted to rekindle their relationship in 2009 but officially called it quits and moved on.
10.Dean McDermott left his TV personality wife for another costar, only to later cheat on his new wife after they were married with four children.
Reality star Dean McDermott was married to Canadian TV personality Mary Jo Eustace for 12 years before he started filming the Lifetime TV movie Mind Over Murder with married costar Tori Spelling. Dean and Tori fell in love, and he filed for divorce during filming. They married each other the next year. After starring in multiple reality shows together and sharing four children, Dean reportedly cheated on Tori while in Canada.
11.Ozzy Osbourne's reps claim he had a sex addiction when it was revealed he cheated on his wife, Sharon Osbourne, multiple times.
In 2016, English singer Ozzy Osbourne was caught cheating on Sharon with their family hairstylist, Michelle Pugh. While Pugh felt the relationship was serious, Ozzy's reps claimed that he was struggling with sex addiction and it was a mistake. Sharon has claimed there were more affairs, including catching Ozzy in bed with two nannies.
12.Kristen Stewart's highly publicized affair while dating Robert Pattinson was only the beginning of her infidelity rumors.
While dating Twilight (2009) costar Robert Pattinson, Kristen Stewart had an affair with Snow White and the Huntsman (2012) director Rupert Sanders. Rupert was married to Liberty Ross, who also starred in the film. Following the end of their relationship, US Magazine reported that Kristen left her new partner, Alicia Cargile, for French singer Stephanie "Soko" Sokolinski and allegedly cheated on Soko with Alicia. It was also rumored that while she dated Stella Maxwell, Kristen was allegedly caught with Alicia again.
13.Eddie Cibrian had two affairs while married to a Real Housewives star, one of which resulted in his marriage to the famous country singer LeAnn Rimes.
Actor Eddie Cibrian is known for cheating on his then-wife, Real Housewives of Beverly Hills star Brandi Glanville, with country singer LeAnn Rimes. Eddie also cheated on Brandi with Vanderpump Rules star Scheana Marie Shay while he was married. Eddie and Brandi divorced, and he married LeAnn in 2011.
14.Ben Affleck left one actor named Jennifer for the next, only to allegedly have an affair with an SNL producer.
While he was with then-fiancée Jennifer Lopez, Ben Affleck began a relationship with Jennifer Garner on the set of Daredevil (2003). Garner was married to actor Scott Foley at the time. In 2017, Ben and Jennifer Garner filed for divorce. During this time, he reportedly had an affair with Saturday Night Live producer Lindsay Shookus while she was married to her SNL colleague, Kevin Miller.
15.Claire Danes fell for not one, but two, of her costars while she was already in a relationship.
Actor Claire Danes and singer Ben Lee were together for years when the rumor that she became involved with actor Billy Crudup surfaced. Billy was with Weeds star Mary-Louise Parker, who was pregnant at the time. A few years later, Claire quickly moved on from Billy to her Evening costar Hugh Dancy. She also admitted to having another affair while courting Hugh Dancy, which helped her decide she was going to marry him. The pair were married a couple of years later.
