There’s an old saying about love and relationships when it comes to men, which is that a man is only as faithful as his options. And while I would like to think that most men don’t look at the world that way, there are admittedly quite a few people in the world who prove this statement to be true, but that is not just limited to men. Men might be known as the ones that are more likely to cheat, but there are plenty of women in the world who want to have their cake and eat it too, and some of them are actually incredibly shameless in their game.
Of course, when it comes to having options, beautiful and famous women are obviously going to have a lot more appealing offers for anything and everything than most other people would have, so it’s not a huge surprise that at least some of them choose to sample a whole variety of dudes (or even the occasional woman, if you’re Angelina Jolie) without really concerning themselves with their current relationship or the relationships of their cheating partners. But out of all of the famous cheating women in the world, who are the worst offenders? Who seems to like cheating the most, who likes to go after married men the most, and who just sucks at covering their tracks the most? There are plenty of cheaters and affairs to choose from, but let’s take a look at a few of the most legendary.
15. Angelina Jolie
Angelina Jolie has a reputation as being one of Hollywood’s biggest man-eaters, which is interesting considering that she has only ever had a handful of public relationships. However, that’s not to say that she hasn’t earned that reputation, either. Jolie’s two most famous conquests are Billy Bob Thornton and Brad Pitt, both of whom were in very serious relationships when they took up with Angie. Angelina met her ex-husband Billy Bob Thornton on the set of their movie Pushing Tin, and after a few weeks of playing an imaginary couple the pair decided to tie the knot for real. The only thing was that Billy Bob was actually already engaged to actress Laura Dern. To hear her describe it, she went off to film a movie and came back to find her fiancé married to another woman. Apparently the two never even spoke again after that. And then of course there is the legendary Brangelina and Jennifer Aniston situation, where Angelina and Brad fell for each other during the filming of Mr. And Mrs. Smith and busted up the most famous marriage at that time.
14. Britney Spears
Britney Spears has certainly had some ups and downs when it comes to her dating life, but her late teens and early 20s were probably her wildest times when it comes to relationships and cheating. Of course, Britney’s most famous ex is fellow pop superstar Justin Timberlake, who she dated from 1999 to 2002. However, Spears seemed to have some trouble staying faithful in that relationship, as she was rumored to hook up with dance choreographer Wade Robson, Eminem, and Fred Durst towards the end of her relationship with Justin. And while no one can say for sure if these are true, or which ones might be true, but considering the Britney doppelgänger who starred in Justin’s video for “Cry Me A River,” I think it’s safe to assume that at least some of the rumors are true. Britney then married Kevin Federline, and supposedly had a few dalliances with some other men during that relationship too.
13. Gabrielle Union
Gabrielle Union is a successful actress who recently married basketball superstar Dwayne Wade and looks like she ages in reverse, so by all appearances you’d think she has it really made in the shade. However the actress has a bit of a rumored reputation for going after men who aren’t single, and if the old adage “once a cheater always a cheater” is true then it seems like a pretty likely scenario. Union has been married twice, once to football player Chris Howard and currently to Dwayne Wade, but she has publicly discussed the fact that both partners have cheated on her before (with one of Wade’s cheating episodes actually resulting in a baby). Union also admitted openly to cheating on Howard multiple times, but said that their marriage was a bad idea from the start and she knew she shouldn’t have gone through with it. Wade and Union seem to have worked through the cheating issues for now, but whether or not they can keep it together remains to be seen.
12. Jessica Simpson
Jessica Simpson has actually gone on to have a pretty long and diverse career considering where she came from. In the early 2000s she was just a middling hot pop singer in a market that was already oversaturated with hot pop singers, and honestly, one of her biggest claims to fame was that she was the only performer in her genre who was loudly, genuinely dedicated to remaining “inexperienced” until marriage. Revolving your professional persona around this is a little creepy, but she was the daughter of a pastor and seemed to be legitimately very religious, so at least it seemed genuine, and she married fellow singer Nick Lachey in her early 20s so it wasn’t an abnormally long wait anyway. However, once she got the ball rolling it seemed like she really wanted to make up for lost time. In the years following her marriage to Lachey she reportedly hooked up with Johnny Knoxville, Bam Margera, John Mayer, Jared Leto, Dane Cook, Fred Durst, and Adam Levine. And those are just the guys she was rumored to hook up with before her marriage to Lachey ended.
11. Sienna Miller
Sienna Miller is a moderately successful English actress who has managed to stay out of the tabloids for a few years running now. However, when she first burst on to the scene her public profile was more about who she was dating than about her actual acting and performances. Her first super high profile relationship was with fellow English actor Jude Law, who was still married to his wife Sadie Frost when their relationship began. And as the saying goes, once a cheater always a cheater. While Jude and Sienna were together Jude cheated on her with his children’s nanny, which led to their relationship becoming very on and off, with Miller dating a few guys in between. Miller’s romantic life made headlines again a few years later when she was photographed without a top on a boat and getting cozy with actor Balthazar Getty, who was also married at the time that the photographs were taken.
10. Jennifer Lopez
Jennifer Lopez has admitted herself that she’s in love with the idea of being in love, and her dating history certainly shows that. Not only is her ex list littered with some very famous and completely unknown names, but a few of those relationships seem to overlap or seem to have come about when her new partners still hadn’t ditched their old partners quite yet. J-Lo’s most famous string of relationship overlaps probably started when she was dating Sean Combs, a.k.a. Puff Daddy. She and Combs were pretty serious for quite a while, that is until Jenny abruptly married her backup dancer Cris Judd. Lopez and Judd lived in wedded bliss for a bit, before Jennifer entered into one of her most famous relationships with Ben Affleck, and the duo was affectionately dubbed Bennifer. But it looks like Bennifer began before Lopez’s marriage to Judd was over. Then, of course, Jen dumped Ben and moved on to Marc Anthony, who she was married to for 10 years. However Anthony was married to former Miss Universe Dayonara Torres until June 1st 2004, a whopping 4 days before Anthony married Lopez.
9. Katharine McPhee
Katharine McPhee is most known for her appearance on the reality show singing competition American Idol, but since her appearance on the show she has actually carved out a pretty decent acting career for herself. And while she hasn’t been one to be very public about her personal relationships, McPhee was actually married to a man named Nick Cokas for quite a few years after her American Idol rocket to fame. And as Katharine’s acting career found its legs she wound up landing a lead role on the NBC drama Smash, which seemed to be a pretty solid step up from where she had been before. Through that job she met series director Michael Morris, and the pair actually started a relationship on the set of the show. McPhee and her now ex-husband Cokas differ on what exactly happened, though. Katharine claims that she and Cokas were already split up when the relationship with Morris began and they just hadn’t filed the paperwork yet, whereas Cokas claims that they were together at the time and the affair was the direct cause of their separation.
8. Kris Jenner
Unlike a lot of other entries on this list, Kris Jenner is actually a self-admitted serial cheater. The reality TV star talked in detail about the multiple affairs she had while married to lawyer Robert Kardashian, and some of the more interesting entries on the list were an affair with her tennis instructor Todd Waterman, one with her hairstylist Alex Roldan, and even one with super famous football player and murderer OJ Simpson (and if that weren’t strange enough, Robert Kardashian was also one of OJ’s defence lawyers for the Nicole Simpson murder trial). One of the nastier side effects of Kris’ marital infidelity is the constant speculation that Khloe Kardashian might not be the biological daughter of Robert (both Roldan and Simpson have been theorized to be her real biological parent). However, given Khloe’s facial similarities with Robert it seems unlikely. And interestingly, despite the cheating and eventual divorce between the Kardashians, Kris says that one of her greatest regrets in life was divorcing Robert.
7. Leann Rimes
Leann Rimes actually hasn’t had many high profile relationships during her career in entertainment, which began when she was extremely young. However, her relationship with Eddie Cibrian has gotten the most press coverage out of any of her relationships, and that’s not just because he’s the most well known person she’s been in a relationship with. Leann met Eddie when they were filming a TV movie together, and they began their relationship almost as soon as they met because they hit it off so well. However, both the singer and the actor were married to other people at the time. Cibrian was married to Real Housewives star Brandi Glanville (who he had two children with) and Rimes was married to Dean Sheremet. But after Leann and Eddie were busted by some snooping paparazzi, their affair became national news, and both of their marriages ended soon afterwards. The couple wound up getting married themselves, but both of their former flames seem to have some pretty understandable sour grapes feelings over the whole situation.
When it comes to stars who have cheated on their spouses, Snooki is kind of in a league of her own, because she actually committed at least a few of her cheats while she knew she was being filmed for Jersey Shore. Nicole “Snooki” Polizzi is currently married to the sweetheart she met while filming Jersey Shore, Jionni LaValle, but their road to the altar was not a smooth or easy one. On the show Jionni was visibly upset by Nicole’s party girl behavior and the couple went through a few on and off periods during filming before finally getting together for good after the show ended. But Snooks didn’t cope with her relationship problems very well, and she seemed to have a habit of turning to fellow Jersey Shore star and housemate Vinny Guadagnino when she was feeling down about Jionni. Nicole ultimately came clean with her cheating shortly after each hookup, but she also didn’t have much choice since the hookups were going to air on TV.
5. Kristen Stewart
Kristen Stewart and Robert Pattinson were probably the most famous couple in the world for a while, since they were both the leads in the most successful film franchise at the time, Twilight. But their relationship ended not long after the franchise did, and it wasn’t just because the couple had grown apart or didn’t want to be together anymore. Stewart was in the process of filming another movie called Snow White and the Huntsman with Charlize Theron and Chris Hemsworth, and apparently she took a liking to the film’s director, Rupert Sanders. But Stewart didn’t bother breaking up with Pattinson before starting up with Sanders, and Sanders was actually married with two children at the time too. The pair wound up getting outed because a photographer caught them snuggling on an outing, and the affair abruptly ended both other relationships while getting a lot of ire from the public. But Sanders and Stewart didn’t stay together either.
4. Tori Spelling
Tori Spelling has been pretty open with the public about a lot of aspects of her personal life, so it’s no surprise that she has been open about her relationship with now husband Dean McDermott. When Spelling and McDermott first met (while filming a movie together, which seems to be a popular place for entertainment industry affairs to start) Tori was married to her first husband Charlie Shanian and McDermott was also married to his first wife Mary Jo Eustace, but neither marriage stopped the pair from starting their own relationship together. Of course, the couple was discovered not long after the affair began, and both Spelling and McDermott decided to divorce their current spouses and planned on getting married to each other. Their relationship was met with some hostility though, and not just from their current partners. Tori’s mom Candy strongly discouraged Tori from divorcing Charlie (who she apparently liked a lot) and even vowed to cut off a lot of Tori’s money supply from the Spelling estate if she went through with it. But she did go through with it, and Tori and Dean have been married and near broke ever since.
Madonna is pretty well known for her outrageous behavior, so it’s no surprise that her romantic life would include some pretty outrageous behavior as well. Madonna has been in quite a few famous relationships too, and rumor has it the beginning and end of some of these relationships wasn’t totally on the up and up. One of Madonna’s most obvious cheating relationships was with baseball player Alex Rodriguez, because A-Rod was married when their relationship began and his wife cited an affair as one of their reasons for the divorce when she filed the paperwork. And Madonna’s longest relationship was with English film director Guy Ritchie, but rumor has it that Madonna’s issues with infidelity may have been a contributing factor to that breakup as well. Ritchie was a tad vague on the reasons behind their split. However, he did say that living with her was like living in a soap opera and that her strict, controlling nature was very hard to deal with.
2. Whoopi Goldberg
When you think of famous Hollywood vixens, Whoopi Goldberg probably isn’t the first entertainer who comes to mind. However, Whoopi is actually another self-admitted serial cheater. Whoopi has actually been married a whopping four times between the early 70s and early 90s, and has said that she had “messed around” behind her husbands’ backs around half a dozen times during her marriages. She declined to discuss the affairs further, but was pretty flippant about the admission and seemed to think that the occasional cheat was a pretty normal thing to be doing. Whoopi’s former husbands were not men who are well known in the entertainment community, but some of her more famous former flames include people like Ted Danson, Danny Glover, former James Bond star Timothy Dalton, and surprisingly even famously reclusive comic book writer Alan Moore. But since Whoopi hasn’t made any legal vows of faithfulness to a man since the 90s, perhaps she realized that fidelity isn’t one of her strong suits.
1. Elizabeth Taylor
When it comes to legendary Hollywood femme fatales, no one can really top Elizabeth Taylor. She’s such a legend when it comes to Hollywood romance that most people still know about what a man eater she was even though her most famous romantic exploits took place over 50 years ago. The stunning actress was married a shocking seven times, mostly to fellow actors or other obscenely rich men like Conrad Hilton or Richard Burton (twice), but her most legendary affair was probably with singer Eddie Fisher. When Elizabeth first took up with Fisher he was already married to Debbie Reynolds and they had two children together (one of them being Princess Leia herself, Carrie Fisher), and Taylor and Reynolds were actually best friends before the affair was discovered. Fisher decided to divorce Reynolds and marry Taylor, and the trio essentially became the Brad, Angelina, and Jennifer Aniston love triangle of the 1950s.
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