Is it fair to call these 15 celebrities ‘serial cheaters’?

Tiger Woods

Tiger Woods cheated on his now-ex-wife Elin Nordegren with over 120 women, according to reports. Following the messy end to their marriage in 2010, Woods then started another relationship with Olympic skier Lindsey Vonn. That relationship also ended amid rumors that Woods cheated once again, though he denied it.

Hugh Grant

The first of Grant’s public indiscretions started all the way back in 1995 when he was arrested for lewd conduct when he was caught in his car in Hollywood with a prostitute named Divine Brown. He was dating Elizabeth Hurley at the time.

More recently, Grant said in a 2016 interview with Howard Stern that he is all for infidelity in marriages. “I’ve always admired the French and the Italians, who are very devoted to their marriages and take them extremely seriously, but it is understood that there may be other visitors at 5 o’clock in the afternoon. You never boast about it, you never say anything, but it keeps you together.”

Elizabeth Taylor

Elizabeth Taylor was notorious for going through men. She was married eight times, after all. But none of her dalliances were so scandalous as her relationship with Richard Burton. When Taylor met Burton, she was married to Eddie Fisher, whom she’d stolen from Debbie Reynolds. She quickly left Fisher, however, for Burton, which was a big scandal at the time. 

Jesse James

Jesse James has a history of cheating on his spouses, most notably Sandra Bullock and Kat Von D. Just a few days after Bullock gushed about her husband at the 2010 Academy Awards, reports of her hubby’s affairs broke. After Bullock and James ended their marriage, he started a relationship with Von D. They quickly got engaged, but the relationship was over by the end of Septemeber when Von D revealed James had cheated on her with at least 19 other women.

Ashton Kutcher

When Ashton Kutcher was married to Demi Moore back in 2012, he reportedly wasn’t faithful at all. Scott Eastwood even outted Kutcher on Watch What Happens Live, saying that Kutcher cheated on Moore with Eastwood’s girlfriend at the time. Ouch! Now, Kutcher is married to Mila Kunis and the two have started a family. Kunis is pregnant with the couple’s second child.

Jude Law

Jude Law was married to fellow actor Sienna Miller for less than a year before it was revealed he’d been having an affair with the nanny in 2005. The nanny, Daisy Wright, went on to do a tell-all interview in which she gave sordid and intimate details of the affair. Miller and Law separated in 2006. 

Brad Pitt

Everyone who knows anything about Hollywood A-listers knows the rumors surrounding the Brad Pitt, Jennifer Aniston, Angelina Jolie love triangle. Pitt and Aniston were married until Pitt started working on 2005’s Mr. and Mrs. Smith with Jolie. Though Jolie and Pitt maintained they didn’t do anything until after Pitt was divorced, no one’s ever been too convinced. That’s all come back to the surface now that Pitt and Jolie have announced their divorce. Rumors swirled that Pitt had an affair with Marion Cotillard, though she shot down those rumors real quick.

Jack Nicholson

That raspy voice isn’t the only thing Jack Nicholson is known for. Nicholson had a long-term relationship with actress Anjelica Huston until Nicholson broke the news to her that he had gotten another woman pregnant in 1990. There are even reports that Nicholson romanced Meryl Streep back on their 1986 film Heartburn.

David Letterman

David Letterman came clean about his affairs during a 2009 interview with Oprah. He admitted that he had sex with women who worked for him on The Late Show, including his assistant Stephanie Birkitt. Birkitt then threatened to write a screenplay about Letterman’s affairs. Letterman’s wife Regina Lasko stuck by his side despite the scandals, and the two are still married. 

Arnold Schwarzenegger

Oh Arnold… The governator’s affairs were revealed in 2011 after the LA Times reported that he’d had a long-term affair with his housekeeper, Mildred Baena. He was also the father of her child, which she had all the way back in 1997. This sordid love affair wasn’t the first time Schwarzenegger cheated either. He admitted in his memoir, Total Recall, that he had a “hot affair” with Brigitte Nielsen in 1985.

Ingrid Bergman

Ingrid Bergman ruined her Hollywood image when it was revealed that she had an affair in the early 1950s with director Roberto Rossellini. Both were married to other people at the time. Bergman got pregnant with Rossellini’s love child and the two left their respective spouses to marry one another. The scandal was so heated that Bergman left America for Europe until 1956, when she came back with her Oscar nomination for the film Anastasia.

Charlie Sheen

It’s hard to remember, but there was a time before Charlie Sheen was known for his scandals. Sheen reportedly cheated on wife Denise Richards with his assistant. The two divorced in 2006. He then went on to marry Brooke Mueller, who he also reportedly cheated on with multiple prostitutes. Their marriage ended in 2011.

Josh Duggar

Of course Josh Duggar made this list. Josh broke the Duggar family’s image as the perfect, conservative Christian family that starred on TLC’s reality show 19 Kids and Counting. He was on the dating website Ashley Madison and was reportedly addicted to pornography. He also inappropriately touched his sisters as a teen. Though Josh and his wife Anna Duggar are now on the road to piecing their lives back together, many aren’t certain Josh will ever be the good husband Anna thought she married.

Scott Disick

Scott Disick and Kourtney Kardashian have always had their ups and downs throughout their long-term relationship, but all hell broke loose when he was caught cheating on Kardashian with Chloé Bartoli while vacationing. Kardashian ended the relationship and Disick checked himself into rehab. Now, it seems like Disick has moved on to a better place in his life, but can it last?

Kristen Stewart

Kristen Stewart seemed to have a real life fairy tale with boyfriend Robert Pattinson. Unfortunately, it wasn’t to have a happy ending. Stewart was caught kissing her Snow White and the Huntsman director Rupert Sanders in 2012, and her relationship with Pattinson crumbled from there. Kristen Stewart has now moved on to dating women, which she says is more her speed. 

Woody Allen

Woody Allen had probably the strangest affair in the history of Hollywood affairs, and that’s saying something. In 1992, Allen was in a relationship with actress Mia Farrow, but it crumbled when it was revealed that Allen was having an affair with Farrow’s 21-year-old adopted daughter Soon-Yi Previn. The creepy part is that Allen and Farrow had been together since 1979, when Previn was just a little girl. Allen had been like a father figure to her as she grew, though Allen insisted that was never his role. Whatever the case, Allen and Previn married in 1997 and have been together ever since.

Claire Danes

You might not have expected to see Homeland actress Claire Danes on this list, but it turns out she has a history of cheating. It first started back in 2003, when Danes and her then-boyfriend Ben Lee split among rumors that she had started an affair with her Stage Beauty co-star Billy Crudup. She and Crudup dated until 2007, when she met her now-husband Hugh Dancy. She reportedly started something with Dancy before things had ended with Crudup. Now that she and Dancy are married and settled down, perhaps Danes has moved on from her cheating past. 

John F. Kennedy

Who can forget the rumors that Marilyn Monroe and John F. Kennedy had a secret love affair? Happy birthday, Mr. President, indeed. In fact, this is a picture of Monroe singing to Kennedy at his birthday party in 1962. There are even rumors to this day that Jackie Kennedy was so fed up with John’s affairs that she was ready to divorce him.