pinterest-p mail bubble share2 google-plus facebook twitter rss reddit linkedin2 stumbleupon
The Premium The Premium The Premium

14 Hollywood Cheaters Who Upgraded

Most Popular
14 Hollywood Cheaters Who Upgraded

via TheRichest

Celebrities seem to be the worst of us; they never stay faithful for too long.  As fans, it’s hard for us to watch so many celebrity marriages fail due to infidelity- it kind of robs us of the hopes of having a stable relationship ourselves.  However, we can take solace in the knowledge that celebrity marriages are practically otherworldly, with all the added obstacles they face.

There are plenty of cases where infidelities occurred and it didn’t work out too well for the cheater.  Ben Affleck, Jude Law, and Ethan Hawke are just a few of the many celebrities that ruined their marriages by sleeping with the family nanny; some of them are now paying child-support for a baby mama they didn’t even want to stick with in the first place.  So many times, cheaters end up berated by the media and fans, having their wealth divided, and left alone to rebuild their awful reputations- just look at a cheater like Jesse James.

Some of the celebrities on this list have committed several infidelities, seeming to cruise through relationships as if their lives were a Game of Thrones and they were using each romantic partner until a more advantageous match arose.  It’s certainly one way to climb the social and financial ladder, but not really the most admirable or noble way to do it.  Yet plenty get away with it and somehow come out winning!

So here they are, the dirty rotten scoundrels: 14 Hollywood celebrities that cheated and upgraded to a better partner.

14. Jennifer Lopez – From Cris Judd to Ben Affleck

via shutterstock.com

via shutterstock.com

Back in the days of Jennifer’s blossoming music career, she met actor/dancer/director Cris Judd in Spain when he was hired to direct her “Love Don’t Cost a Thing” music video.  The two hit it off and got married in September of 2001.  It was Jennifer’s second marriage (the first was to a Cuban waiter, Ojani Noa), and it seemed like she figured it out the second time around.  Unfortunately, the couple didn’t last very long.

They divorced the following June (not even a full year after marrying), very suddenly and quietly.  She shortly thereafter began a high-profile relationship with Ben Affleck, who was then at a peak of his career with movies like Pearl Harbor and Good Will Hunting under his belt.  Judd remarried years later and has made a career out of guest starring on reality TV shows.  Jennifer certainly traded up from her back-up dancer hubby to the highly successful Ben Affleck.  However, there always seems to be trouble in paradise…

13. Marc Anthony – From Dayanara Torres to Jennifer Lopez

http://i.dailymail.co.uk/i/pix/2014/06/13/article-0-1EB84C9A00000578-25_634x784.jpg

via dailymail.co.uk

It’s hard to say exactly when Jennifer began to stray from Ben Affleck.  Perhaps it was when the romantic comedy they made together, Gigli, bombed in theatres.  Maybe it had something to do with the weird chemistry he had with Jennifer Garner in Daredevil, not to mention that that movie also stank; or maybe they just generally lost interest in each other.  In any case, Jennifer sought comfort in the arms of her longtime friend, singer Marc Anthony, and it certainly paid off for him!

At the time, Marc Anthony was married to actress/beauty queen Dayanara Torres.  The two had an affair and promptly divorced their significant others to pursue a relationship with each other.  In retrospect, Jennifer certainly traded down for Marc, but he certainly traded up for the still highly successful Jennifer Lopez.  The two ended up divorcing after ten years of marriage but, in Hollywood terms, the two had a good run.

12. Mel Gibson – From Robyn Moore to Oksana Grigorieva

via shutterstock.com

via shutterstock.com

Once upon a time, before Mel Gibson was known as a crazy old anti-Semite and was more commonly known as the original Mad Max, he met Robyn Moore, a dental nurse in southern Australia.  They fell in love and were married for 26 years.  Then, suddenly, they weren’t happy anymore.  The two cited “irreconcilable differences” as the cause of the rift in their relationship, however, we all knew the true reason they divorced as photos were leaked of him with Russian pianist Oksana Grigorieva before the divorce was even filed.  Assuredly, Gibson had managed to trade up from a middle-aged housewife to a young artist.

As a side-note, Grigorieva split from Gibson not long after having his child, claiming that he had assaulted her.  This was in 2010, about the same time he was berated for his racism, sexism, and anti-Semitism.  Suffice to say, Gibson traded up but was too crazy to keep the goods.

11. Gwen Stefani – From Gavin Rossdale to Blake Shelton

via shutterstock.com

via shutterstock.com

In 1995, the bands No Doubt, the Goo Goo Dolls, and Bush all went on tour together.  While on tour, No Doubt front-runner Gwen Stefani met and fell in love with Bush guitarist Gavin Rossdale.  After dating on-and-off for many years, the two married in 2002.  The two had three kids together and seemed very happy.  Gavin’s career slowed, though Gwen kept busy with music and then judging on The Voice.  All of a sudden, Gwen demanded a divorce.  So what happened?

It all goes back to The Voice.  While a judge on the show, she met country singer Blake Shelton and the two hit it off.  Gwen and Gavin divorced and, only a month later, Gwen announced she was dating Blake.  The two are already engaged and are planning to wed later this year.  Gwen certainly traded up, from has-been Gavin to country idol Blake Shelton.

10. Leann Rimes – From Dean Sheremet to Eddie Cibrian

via shutterstock.com

via shutterstock.com

Country singer/songwriter Leann Rimes met backup dancer Dean Sheremet at the 2001 Country Music Awards.  She instantly knew that he was the love of her life and the two got married only a year later.  However, the two weren’t together forever; their marriage ended only eight years later.  What happened?

Northern Lights, a Lifetime made-for-TV-movie, happened.  Leann did film work when it was presented to her, meaning she did a lot of low end and made-for-TV movies, and she always enjoyed the process; but she never enjoyed it as much as she did on Northern Lights.  There, she met co-star Eddie Cibrian, a small time TV actor best known for his small roles in Baywatch Nights, Sunset Beach, and The Cave.  Leann left Dean Sheremet in a messy and unilateral divorce and she pursued Eddie.  They married in 2011 and have been together ever since.  She upgraded from backup dancer to small time TV actor; it was a small upgrade, but an upgrade nevertheless.

9. Eddie Cibrian – From Brandi Glanville to Leann Rimes

via shutterstock.com

via shutterstock.com

Oh, did we forget to mention?  Eddie Cibrian was married with children when he had his 2009 extramarital affair with Leann Rimes.  He’d married model and Real Housewife of Beverly Hills Brandi Glanville back in 2001 and the couple had two sons.  The family unit seemed secure and safe and happy, until that damn Northern Lights (Lifetime Network ruins everything).

Perhaps what is most unfortunate is that Brandi didn’t learn of his infidelity by hearing it from Eddie; oh no, she found out through media coverage of romantic encounters Leann and Eddie thought were private and secret.  Brandi divorced Eddie, taking a good portion of his estate.  Leann publicly apologized for ruining the marriage but added, “I don’t regret the outcome.”  Brandi has since focused on raising the children Eddie left her with.  Eddie certainly traded up for a wealthier wife and more exhilarating life.

8. Billy Bob Thornton – From Laura Dern to Angelina Jolie

via shutterstock.com

via shutterstock.com

Billy Bob Thornton, an American actor made popular from films like Armageddon, Sling Blade, and Princess Mononoke, had been married four times before he thought he had finally gotten it right with his marriage to American actress Laura Dern, who is popular from her roles in Jurassic Park, Blue Velvet, and The Fault in Our Stars.  The two started dating in 1998, but Billy Bob had another surprise in store for him.  Only a year later, he became close with Angelina Jolie when they made the movie Pushing Tin.  Billy Bob left the girl-next-door type, Laura Dern, for the ultimate babe, Angelina Jolie.

The two were grossly affectionate, even going so far as to wear vials of each other’s blood around their necks (ummm, ewww).  They married in 2000 and even adopted a Cambodian child together in 2002.  However, it apparently wasn’t all green pastures and sunshine for the couple.  They officially divorced in 2003, admitting they brought out weird sides in each other.

7. Brad Pitt – From Jennifer Aniston to Angelina Jolie

via shutterstock.com

via shutterstock.com

Billy Bob wasn’t the only one that realized he could cash in for a better prize in Angelina Jolie.  Heartthrob Brad Pitt started dating Friends star Jennifer Aniston back in 1998.  They were a hot-ticket item; everyone gushed over seeing the adorable couple in tabloids and on red carpets.  They married in 2000, and everyone thought this crazy couple would be the ones that got it right.  Well, we were wrong.

In 2005, Brad Pitt made the movie Mr. & Mrs. Smith, a romantic action movie about a super spy couple, with Angelina Jolie.  The two took their roles a little too personally and fell for each other – hard.  Brad divorced Jennifer in 2005 and immediately started a relationship with Angelina Jolie, whom he is still married to and has three natural and three adopted children with.  To this day, there are those that debate “Team Angelina” versus “Team Jennifer,” but it’s hard to argue that Brad didn’t upgrade. Jennifer’s great, but she’s not UN ambassador, world’s sexiest woman great.

6. Madonna – From Guy Ritchie to Alex Rodriguez

via shutterstock.com

via shutterstock.com

Singer/songwriter Madonna met director Guy Ritchie, who was then popular for directing and writing Lock, Stock and Two Smoking Barrels, back in 1998.  The two had a child together in 2000 and then married the day after their newborn son was christened.  Thought they were happily married, they spent most of their time focused on their careers: Madonna went on her Drowned World Tour, and Guy directed some of his most popular films, including Snatch and Swept Away (in which Madonna starred).

Unfortunately, in 2008, Madonna strayed from Guy Ritchie with famous Yankees baseball player Alex Rodriguez (though they never admitted the relationship was romantic, what else could they be doing during all those late night meetings at her NYC loft?).  She realized how discontented she was in her marriage to Guy and the two divorced over “irreconcilable differences.”  She thought she was trading up from then small time director to famous MLB player, however, she realized Rodriguez wasn’t interested in pursuing a serious relationship.  She then ended her fling with Rodriguez and adopted a child from Malawi.

5. Meg Ryan – From Dennis Quaid to Russell Crowe

via shutterstock.com

via shutterstock.com

Meg Ryan, most popular from her roles in romantic movies like Sleepless in Seattle, You’ve Got Mail, and When Harry Met Sally, married Dennis Quaid, who was then most popular for his roles in Jaws 3-D, The Long Riders, and The Big Easy. They met while filming the movie D.O.A. together and they fell for each other.  The two were good for each other; they eased into their relationship, she got him to end his cocaine addiction, and they had a child together.  They married in 1991, then divorced in 2001 because of an extramarital affair with Russell Crowe.

In 2000, Russell and Meg were filming Proof of Life and were unable to separate their personal feelings from the feelings of their characters.  Meg thought she was in love, and traded away the (then) moderately successful Dennis for the wildly successful gladiator, Russell.  Though she had every intention of staying serious with Russell, she noticed her relationship was just as unhealthy with him as it was with Dennis.  She’s single now, unable to hold on to the upgrade that was Russell Crowe.

4. Billy Crudup – From Mary Louise Parker to Claire Danes

via nydailynews.com

via nydailynews.com

“Who the hell is Billy Crudup?” you may ask.  Billy is an American actor best known for his roles in Watchmen (Dr. Manhattan), Almost Famous (Russell Hammond), and Big Fish (Will Bloom).  Though he’s had a very expansive and successful career, he’s rarely featured in tabloids and media.

Billy Crudup dated Mary Louise Parker, who is famous for her roles in Weeds, RED, and Angels in America, for three years.  In 2003, Mary became pregnant with Billy’s son.  Yet, this somehow didn’t deter him from straying from Mary and sleeping with actress Claire Danes, when Mary was SEVEN MONTHS PREGNANT!  At the time, Mary Louise Parker didn’t have a ton of notable work behind her and it seemed he was upgrading to the more prolific actress, who had at that point been in Terminator 3: Rise of the Machines and Romeo and Juliet.  However, Claire doesn’t have a reputation for staying with the same guy for too long…

3. Claire Danes – From Billy Crudup to Hugh Dancy

via huffpost.com

via huffpost.com

Yes, that’s right: the cheater got cheated on, and it’s hard to say he didn’t have it coming.  While dating Billy Crudup, Danes met Hugh Dancy on the set of Evening in 2006, and the two fell for each other.  Yet, Claire didn’t feel the need to break up with Billy before starting a relationship with Hugh!  They dated in secret while filming the movie in Rhode Island, and only when the movie was done filming and she had to return to Billy did she leave him to date Hugh on a more permanent basis.

It seems like Claire might have finally stopped climbing the relationship ladder: she married Hugh (her first and only marriage, to note) in a private/secret ceremony in France in 2009.  They have one child together, whom they shelter from the pressing eyes of the tabloids and, though she still acts, she focuses more on philanthropic work with her husband.  She finally traded in for the ultimate model: Hugh!

2. Millie Mackintosh – From Hugo Taylor to Professor Green

via wordpress.com

via wordpress.com

If you’re an American reader, you’re probably thinking, “wait, who are any of these people?”  Millie is heir to the Mackintosh Confectionary fortune, and was a star of the popular UK reality-show Made in Chelsea, which follows the affluent lives of upper class young people in West London (she’s kind of the UK’s version of Kourtney Kardashian).  Hugo Taylor happened to be her costar on the show, as he is co-founder of Taylor-Morris Eyewear and heir to a sizable fortune himself.  The two dated whilst on the show, but Millie is used to getting what she wants when she wants it – and she wanted Professor Green.

Professor Green is one of the hottest UK rappers on the market right now.  The two disregarded Millie’s relationship with Hugo and got to business.  When Hugo discovered the infidelity, their relationship came to a brief halt.  However, Millie definitely upgraded with Professor Green: not only was he eager to marry her, but the two live a wild and exotic lifestyle that only entertainment celebrities can provide.

1. Tori Spelling – From Charlie Shanian to Dean McDermott

via shutterstock.com

via shutterstock.com

Tori Spelling was once an actress, famous for her roles in Beverly Hills, 90210, Trick, and Scary Movie 2, and maintains her fame through reality shows and guest star appearances.  Back in 2004, Tori married playwright and actor Charlie Shanian in a lavish, expensive wedding; they then filed for divorce a little over a year later.  So what happened?  The official report cites “irreconcilable differences,” but it’s pretty clear what was up since she married Dean McDermott less than a month later in Fiji.  Dean, if you don’t recognize the name, is best known for his roles in Open Range, Power Play, and, of course, the reality show Tori & Dean: Inn Love.  Perhaps shockingly, Dean was married with a son before he began his affair with Tori.  He told his wife of the infidelity and she left him, leaving him free to marry Tori.  Though it was another small upgrade, from small-time actor to slightly less small-time actor, the two definitely made a great life and career together.

  • Ad Free Browsing
  • Over 10,000 Videos!
  • All in 1 Access
  • Join For Free!
GO PREMIUM WITH THERICHEST
Go Premium!

Videos