It’s hard to think of an industry that relies more on its employees being beautiful than the entertainment industry. Being super hot is not a requirement for success, but everyone knows that it’s much easier to make it if you already look the part of a Hollywood hottie. And as a result of that, people working in the entertainment industry wind up meeting an endless supply of ridiculously good looking people. And unsurprisingly, hot people tend to be attracted to other hot people, and hot people have an easier time making romantic connections with other hot people.
Given the expectations and requirements of people who live their lives in the public eye it can be hard to say who’s hotter than who. It’s kind of like trying to split hairs between a bunch of tens to figure out who is the super duper hottie and who’s just the super hottie. And of course everyone has their personal preferences and traits that they’re attracted to, but when it comes to celebrities who ditch one partner for another, there is usually something that makes their decision for one over the other more understandable. Sometimes it’s looks, sometimes it’s age, sometimes it’s success, sometimes it’s just that instantaneous chemistry that draws two people together, or sometimes it’s a combination of any or all of these things. But either way, at some point all of these celebs thought they were leaving behind their current significant other for an upgrade, so let’s go through a few of Hollywood’s biggest cheating scandals and the better looking people that these celebs chose to cheat with.
15. Brad Pitt With Angelina Jolie
It’s no surprise to find what is kind of the original ultra famous love triangle of the modern age on this list, and while Jennifer Aniston is clearly no slouch in any department, it is just hard to match the ultimate seductress Angelina Jolie when it comes to snagging a man. Angelina busting up Jennifer’s marriage with fellow superstar Brad Pitt was such a massive scandal that it still makes tabloid headlines over a decade later, and while Brad and Angelina seemed like the ultimate power couple at the time it honestly looks like Aniston may have come out on top. After more than ten years and six children together, Brad and Angelina finally called it quits and seemed to be having a pretty nasty breakup. Aniston, however, still looks nearly identical to how she did in her years with Brad and is now married to multi-talented actor and writer Justin Theroux (who honestly is looking better than Brad these days). She also seems to have much less drama in her life than Brad or Angelina.
14. Billy Crudup With Claire Danes
In one of the uglier entries of Hollywood makeups and breakups, we have the relationship between Billy Crudup and Claire Danes. Crudup had been with actress Mary Louise Parker for seven years when he met Danes, and when he decided to leave Mary Louise for Claire, Mary Louise just happened to be pretty far along in a pregnancy with his child. Mary Louise is certainly a looker on her own, but if you’re panicking at the thought of a long term and settled family life there’s nothing more obvious and stereotypical to go for than a younger woman who doesn’t have all of that inconvenient baggage you’ve saddled her with. Claire and Billy actually lasted for quite a while – more than one would expect for such a messy beginning – but after four years together they decided to call it quits. In the past Danes has talked about how uncomfortable she was with being treated so brutally in the media because of their relationship, but hey, at least her boyfriend didn’t dump her while she was pregnant.
13. Chad Michael Murray With Paris Hilton
To be honest, you can take one look at Sophia Bush and realize that in terms of appearance, Paris Hilton isn’t a huge upgrade. But when Sophia’s husband at the time Chad Michael Murray cheated on Sophia with Paris (and a lot of other women, supposedly) Sophia was just a moderately successful actress on a WB show and Paris Hilton was one of the most famous women in the entertainment scene. After a few months of marriage Chad and Sophia got a divorce, and Chad almost immediately became engaged to a teenage local he had met while filming One Tree Hill. And while Sophia might have been on the lowest rung of the success ladder out of everyone in this trio, it seems like time has done her a lot of favors. She looks great and has been the lead of the NBC hit show Chicago PD for years now, while Paris is a celebrity DJ in Japan or something, and Chad Michael Murray is somewhere out there squinting intensely.
12. Ryan Phillippe With Abbie Cornish
Reese Witherspoon is smart, successful, and beautiful, and honestly it seems like Ryan Phillippe was pretty lucky to land her in the first place, even though he’s also a super attractive guy. However, Reese has always given off a bit of a type A controlling vibe, and honestly, Ryan’s hookup that ended his marriage is a hardcore stunner. Australian actress Abbie Cornish is talented, seems like a pretty relaxed and easygoing girl, and also happens to so smokin’ that modelling would have been a legitimate career option had acting not worked out. After the affair Reese and Ryan got a divorce and Ryan and Abbie made it official for a while, but considering the lack of apparent animosity between Reese and Ryan, it seems like their relationship might have been coming to an end on its own, anyway. And clearly Reese still came out a winner; she remarried and has had a stellar TV and film career ever since the breakup.
11. Jennifer Lopez With Ben Affleck
Jennifer Lopez definitely doesn’t seem like the kind of girl who likes to be single for long, but sometimes it seems like her relationships have a bit of overlap to them, which is more than a little sketchy. One of those instances was during the end of her marriage to backup dancer Cris Judd. Jennifer married Judd not long after her relationship with P. Diddy fell apart, but about a year after marrying Judd, Jennifer began a whirlwind romance with Academy Award winning actor and writer Ben Affleck. And while there isn’t a lot known about Cris Judd personally, I mean come on… she went from her backup dancer to one of the handsomest most successful actors on the planet. The couple, dubbed “Bennifer” by the tabloid media, became the constant hot topic of entertainment media and that only intensified after they became engaged, but ultimately the pair wound up pulling the ultimate soap opera move and called off the wedding the day before they were set to wed.
10. LeAnn Rimes With Eddie Cibrian
Cheating is always a scumbag move in any circumstance, but to be honest, in the coupling of LeAnn Rimes and Eddie Cibrian it seems like both of them made an upgrade in partners. When LeAnn and Eddie’s affair began, both of them were married. LeAnn was married to Dean Sheremet and Eddie was married to Real Housewife Brandi Glanville. Dean Sheremet wasn’t much of a public figure during his marriage to LeAnn, but someone who looks like Eddie Cibrian is pretty hard to compete with, especially a few years ago when he was really at the top of his game. And Brandi certainly isn’t bad to look at, but she has gone way too far overboard with the plastic surgery while LeAnn has stuck to her more natural beauty. Also, Brandi doesn’t seem like the most pleasant person to be around. Like, when you can distinguish yourself as an exceptionally unpleasant person when you’re on a Real Housewives show, I think that says a lot about your personality.
9. Billy Bob Thornton With Angelina Jolie
Like I said before, when it comes to the art of seduction, it’s pretty much impossible to top Angelina Jolie’s skills. It’s honestly a bit of a surprise that she decided to focus her romantic prowess on someone like Billy Bob Thornton, but she did, and in the process of making one of the kookier couplings in recent Hollywood history Angie also managed to convince her newly found hubby to ditch his fiancée without a word. Billy Bob’s fiancée at the time was actress Laura Dern, and according to her, Billy Bob left their home to film a movie for a few weeks and just never came back. She purportedly found out about her own fiancé’s marriage to another woman through the media and she and Billy Bob never spoke to each other again. Ironically, Angelina’s next relationship after the dissolution of her marriage to Billy Bob was with Brad Pitt, but supposedly it was Billy Bob’s feelings that he wasn’t good enough for Angelina that led to the split.
8. Kevin Federline With Britney Spears
Kevin Federline is pretty much never going to do any better than Britney Spears, but at least the dude seems to understand that, since he has supposedly cheated on his partners twice with her: once before they were married and once after. When Britney and Kevin first hooked up, Kevin was in a long term relationship with Moesha actress Shar Jackson, with whom he shared two children, Kaleb and Kori. But despite sharing two children together, Jackson and Federline remained unmarried, so when an opportunity arose for backup dancer Federline to snag Miss Spears, Kevin didn’t seem to hesitate. Britney and Kevin married pretty quickly after their relationship began and had two kids, Sean and Jayden, pretty much back-to-back. But then the relationship fell apart and Britney went through some rough times. Kevin moved on and became engaged to another woman after their divorce, but supposedly he cheated on his then fiancée with Britney too.
7. Sienna Miller With Daniel Craig
When it comes to the looks department, English actors Jude Law and Daniel Craig are probably pretty evenly matched, but when it comes to personal behavior, it seems like solid relationship guy Craig might be a pretty significant improvement on serial womanizer Law. Actress Sienna Miller came into the spotlight when she and Jude Law began dating, and considering that they met on the set of their film Alfie, it actually looks like their relationship may have started as an affair, because Jude Law divorced his wife around the same time of their filming. If that was the case, then old habits die hard, because after a few years of dating as well as an engagement, it was revealed that Jude cheated on Sienna with his children’s nanny, Daisy Wright. But apparently not one to be outdone, Sienna decided to have a dalliance with Daniel Craig in retaliation for the betrayal.
6. Tiger Woods With A Thousand Women
Tiger Woods really rose to prominence in the sports world not just because of his mad golf skills, but also because he made an incredibly old and stuffy feeling sport seem a little younger and hipper, even if he seemed like a bit of a dork himself. But Woods really struck gold when he hooked up with insanely pretty Swedish nanny Elin Nordegren, with whom he eventually married and had two children. And honestly, I don’t think I’m overstating things when I say that it would be pretty much impossible to find a woman that you could actually say was significantly better looking than Elin Nordegren. However, she is just one woman. And apparently Tiger does not just like having one woman. Tiger seems to have cheated on her with every woman he could, really, and while none of them on their own can really rival Elin’s looks, if someone is more interested than quantity over quality, it’s hard for one woman to beat a hundred others.
5. Tori Spelling With Dean McDermott
To be honest, the relationship between Tori Spelling and Dean McDermott seems to be a bit of a mess, and apparently the old adage “once a cheater, always a cheater” is true (at least in this case) because McDermott has admittedly cheated on Tori in the past, in addition to the fact that both of them cheated on their current spouses when their relationship just began. But from a purely aesthetic perspective, McDermott was a bit of an upgrade from Tori’s first husband Charlie Shanian. However looks aren’t everything, and by all accounts Shanian was a nice guy and a good husband to Tori (not to mention, Tori isn’t much of a stunner herself). But I guess it all tends to come out in the wash anyway, because while Shanian may have been a good partner, it’s obvious that Tori was not, so aside from being a bit of an upgrade in the looks department it also seems like Tori and Dean are a better match because they’re both jerks.
4. Shania Twain With Frederic Thiebaud
You might not be familiar with this whole weird love trapezoid scandal, but it sure is a doozy. Canadian country music superstar Shania Twain was married to music producer Robert “Mutt” Lange since 1993, and the pair had one child together. But apparently at some point in 2010 Shania discovered that her husband was having an affair, with none other than Twain’s long time best friend Marie Anne Thiebaud. The revelation of the affair busted up the marriage between Lange and Twain as well as the marriage between Marie Anne and her husband Frederic, and obviously put a quick end to the former friendship between Shania and Marie Anne. But apparently Shania and Frederic really knew how to make lemonade out of lemons, and the singer and the Swiss Nestle executive leaned on each other throughout the ordeal and obviously connected because of their identical betrayal experiences. And apparently the pair REALLY hit it off, because the pair got married on January 1st of 2011. And it sounds like they both definitely upgraded.
3. Ashton Kutcher With Sara Leal
Ashton Kutcher and Demi Moore seemed like a pretty odd pairing from the start. Aside from the age difference, Kutcher seemed like an exceptionally immature guy for his age while Demi had already had a long marriage to Bruce Willis, and her children with him were teenagers by the time she and Ashton hooked up. But the couple stuck it out for the relatively long haul, and eventually Ashton and Demi wound up getting married, and Ashton actually seemed like a pretty solid husband who cared a lot for Demi’s children. But apparently appearances can be deceiving, because it was revealed that Ashton was cheating on Demi with young blonde Sara Leal. Leal was definitely a regulation hottie, but she also seemed more in line with what most people would be expecting someone like Ashton Kutcher to be with at the time. Their relationship didn’t last, but his marriage to Demi didn’t either.
2. Jason Aldean With Brittany Kerr
It’s no surprise that country music star Jason Aldean had the hots for the cute American Idol alum Brittany Kerr, but unfortunately Aldean was married to his high school sweetheart Jessica Ussery when Aldean first started hooking up with Kerr. After a few tepid denials about their behavior, both Jason and Brittany admitted that their behavior was inappropriate and apologized for any pain it had caused anyone, but the damage was done and Aldean filed for divorce from Jessica after two children and twelve years of marriage. Apparently Aldean’s feelings for Kerr were more than legitimate, though. After divorcing Jessica Aldean and Kerr became engaged, and got married in 2015. The couple welcomed their first child, a baby boy named Memphis, on December 1st of 2017. Clearly the situation should have been handled better, but at the very least both were apologetic about their actions and recognized that they had made a mistake.
1. Jeremy Meeks With Chloe Green
Jeremy Meeks, most commonly known as “prison bae”, appeared on the entertainment scene literally out of nowhere when his jail mugshot went viral and people began commenting on his exceptional good looks and how strange it was that he could take a mugshot that made him look like a model. Apparently some people in the modelling business took notice of that, and once Meeks was released from prison he actually started booking modelling jobs and became a pretty successful male model. But before the meme became a meme and before Meeks became a model, he had been married for eight years to Melissa Meeks, with whom he shared one child. After his meteoric rise to modelling, he said that he wanted to stay with his wife and family, but was later caught smooching Topshop brand heiress Chloe Green on a yacht in Europe. After being exposed, his relationship with Melissa fell apart, and things got serious with Green.
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