Cheating is a huge and usually unfixable mistake that has ended the love lives of couples, even those that love each other so fervently and have been together for decades. Unfortunately for Hollywood, it’s a very common occurrence that anyone can confirm just by following news of stars. Some get together and marry, but they are seen with someone else despite already having a partner. They eventually break up or divorce who they’re with, confirm the rumors, announce that they’re madly in love with the new guy or girl, and finally announce that they will be tying the knot.
From the outside looking in, it seems like the rich and famous lead chaotic, messy and painful love lives with all this infidelity happening. But that’s not always the case, as some relationships that came from less-than-ideal beginnings lead to a happily ever after. At the same time, there are also those that crash and burn, much like the first. And regardless of how these true Hollywood affairs end up, the fact remains that cheating is a huge no-no whether you’re a star or an ordinary person, as it hurts and damages people. Here are fifteen former celebrity mistresses, whose unconventional romances made waves.
15. Britney Spears (Kevin Federline)
Britney’s life is every paparazzi’s dream—from her shot to stardom, her good girl to bad girl image, her sexual explorations, her downfall and comeback and of course, her crazy love life. How crazy? Well, Britney’s first marriage with childhood friend Jason Alexander lasted only 55 hours. Nine months later, she married aspiring rapper and back-up dancer Kevin Federline. That’s K-Fed if you’re cool. Not deterred by her first and unbelievably short-lived first marriage, Britney shacked up with Kevin. She was also not deterred by the fact that K-Fed was, at the time, still with his girlfriend Shar Jackson. As if that’s not bad enough, Shar Jackson was also pregnant with Kevin’s second child when he left her for Britney. That should’ve already been a red flag for Brit, but oh well.
14. Mary Elizabeth Winstead (Ewan McGregor)
Scottish actor Ewan McGregor and Eve Mavrakis’ marriage headed to Splitsville after photos of Ewan and Fargo co-star Mary Elizabeth Winstead getting cozy at The Good Life Eatery in London’s St. John Wood was leaked to the public.
The Trainspotting actor was later seen moving out his beloved artwork from his LA home, which he previously shared with wife Eve and their four children. The couple split quietly over the summer despite the efforts of Eve in fighting through the ordeal. Friends of the couple speculated that Ewan’s mid-life crisis is the reason why he’s pushing through on dating Mary at the expense of his family. Mary, on the other hand, announced her split from husband of seven years the same month that Ewan left Eve.
13. Angelina Jolie (Brad Pitt)
Hollywood’s most famous power couple and once everyone’s one true pairing, Angelina Jolie and Brad Pitt started out in the most unconventional and scandalous way possible, spanning a rift between fans of Pitt, Jolie and Aniston. The high-profile drama that ensued is every tabloid’s dream: A-list starlet snagging the hottest hunk from another beautiful actress.
Pitt and Jolie met on the set of Mr. and Mrs. Smith in 2004, and while both of them denied any on-going romance during that time, the two later admitted that they fell in love on the set. A year later, Friends star Jennifer Aniston divorced Brad Pitt due to irreconcilable differences while Jolie and Brad Pitt did a controversial “Domestic Bliss” photo shoot just six months after the announcement of Pitt’s divorce. A controversial relationship, indeed. And you all know how that ended.
12. Amber Heard (Johnny Depp)
Amber Heard and Johnny Depp’s marriage was short-lived and filled with controversy. To some people, however, the messy split wasn’t much of a surprise, given the fact that the two started with an affair. It has never been confirmed nor denied by the couple, but Amber and Johnny might have had a hook-up while filming The Rum Diary in 2009, despite the fact that Johnny was still with model Vanessa Paradis, his partner of 14 years. Three years later, Vanessa and Johnny announced their split, and Johnny started dating Amber. Come 2015, the two got married, but they filed for divorce a year later, as Amber claimed that the Pirates of the Caribbean star, for the duration of their relationship, had been abusive towards her. Just why, Captain Jack?
11. Jennifer Aniston (Justin Theroux)
Wanderlust stars Jennifer Aniston and Justin Theroux are happily married now, but the start of their relationship might have been not that ideal. Because ironically—or fittingly, perhaps—Justin and Brad Pitt’s ex-wife (and now Justin’s current wife) started the way Brangelina did. Justin Theroux was very much involved with his girlfriend of 14 years, Heidi Bivens, when dating rumors of him and Jen began. The two first met on the set of Tropic Thunder, co-written by Justin with Jen’s closest pal Ben Stiller. It wasn’t until 2010, while filming Wanderlust that the two really got close to each other. After months of dodging rumors about their affair, along with a bitter unofficial ex in tow, the two finally made their relationship public at the MTV Movie Awards after party.
10. Gisele Bundchen (Tom Brady)
Hollywood’s dreamy couple and hottest relationship goals right now – NFL superstar Tom Brady and supermodel Gisele Bundchen’s marriage is a teen movie come to life: varsity jock ends up with cheerleader captain. Even at 40, Tom is still leading his team to championships, while Gisele is still one of the highest paid models in the industry at the age of 37. However, while the two may have the fairy tale romance right now, their dating phase was marred by rumors of infidelity on Tom’s side, as he was in a relationship with actress Bridget Moynahan at the time. Gisele and Tom’s romance overlaps with the end of Tom and Bridget’s relationship, with Bridget announcing her 3-month pregnancy with Tom’s child after she and Tom split.
9. Jennifer Lopez (Marc Anthony)
Grammy award-winning Jennifer Lopez and record producer Marc Anthony first met while Marc was performing in the musical The Capeman. Nothing romantic came out of their first meeting, but according to J-Lo’s memoir, True Love, Anthony’s first words to her were, “ One day you’re going to be my wife.” Before—or rather, during—Jlo, Marc Anthony was married to former Miss Universe Dayanara Torres. But in 2004, the two split, while Jennifer and Marc Anthony got married in secret at Jennifer’s Beverly Hills home. It was never confirmed nor denied that Marc and Jennifer were having an affair while the former was still married to Dayanara, but the timeline of the events leading up to Lopez and Anthony’s nuptials pretty much confirms the rumors of infidelity.
8. Alicia Keys (Swiss Beatz)
We all know Alicia Keys through her bittersweet ballads about love and its many complications. Among her many songs, tracks like “You Don’t Know My Name”, “If I Ain’t Got You”, and “My Boo” come to mind first when people think of Alicia. Her song, “Karma”, on the other hand, not so much. It’s a good song, but it’s a bit ironic for her to be singing about a lover returning after cheating, when she’s the one who Swiss Beatz was dating while he was still married to singer Mashonda. And what goes around doesn’t always come around, because the two eventually tied the knot and had two kids. We guess no one could get in the way of Alicia’s feelings for Swizz—not even his previous marriage.
7. Julia Roberts
Notting Hill was a classy, funny (in a very British way) and sweet romantic comedy, if not a bit too unrealistic. Like, why would the highest-paid, most popular and most beautiful Hollywood actress fall in love with an ordinary guy? Well, it did happen in real life, and fittingly, with Julia Roberts, the very actress that played Anna Scott, the movie’s female lead. She fell in love with cameraman Danny Moder, whom she met on the set of the movie The Mexican. At that time, Julia had a celebrity boyfriend Benjamin Bratt, and Danny was married to makeup artist Vera Steimberg. Six months later, Danny filed for divorce, and was wed to Julia shortly after. Man, It’s Complicated should’ve been Miss Roberts’s movie, not Miss Streep’s.
6. Tori Spelling
One of the biggest names in TV entertainment is Tori Spelling who was in popular series like Saved by the Bell and Melrose Place. She’s well-known for being Canadian-American actor Dean McDermott’s other girl, whom she met on the set of Mind Over Murder in 2005. At the time, Tori was married to playwright Charlie Shanian, which means both sides were having an affair. A year later, due to both of their infidelities, their respective spouses filed for divorce, so the two were finally free to marry each other. However, the grass wasn’t green enough on the other side, as Dean cheated on Tori, and had to go to rehab. Nevertheless, the two are still together, but we can’t help but wonder if Tori regrets marrying Dean or not.
5. LeAnn Rimes
“Can’t fight the moonlight,” so says LeAnn Rimes. The singer, who’s known for songs like “How Do I Live”, “I Need You” and “Life Goes On”, also couldn’t fight the feelings she had for Eddie Cibrian, even though she was already married at the time to backup dancer Dean Sheremet. To make things more complicated (as if they already weren’t), Eddie was also married at the time to TV star Brandi Glanville. The couple’s respective spouses (what a strange thing to say) filed for divorce in 2009, and the next year they were already engaged. The two got married in 2011, and now live in California—a rather happy end after all those twists and turns. Well, hopefully this time it’s truly a happily ever after for her.
4. Ryan Shawhughes
The title of the article can be interpreted in two ways: celebrities who are mistresses, and mistresses of celebrities. For this particular entry, it’s the latter, because Ryan Shawhughes is neither a singer nor actress in Hollywood or of any other country. Rather, she’s the former nanny of Ethan Hawke, Hollywood actor known for movies such as Before Sunrise, Gattaca and The Purge. After Ethan denying many times the allegations of him having an affair with Ryan, he then went on to marry her in 2008—five years after his wife Uma Thurman, who’s famous for movies like Pulp Fiction, Kill Bill and, well, Gattaca. Lots of Hollywood actors have cheated on their spouses with the nanny, but Ethan is one of the few who tied the knot with one.
3. Miranda Lambert
You know how it goes: new girl comes into a married man’s life, the new girl becomes the wife and then the wife eventually cheats on her divorcee husband with another guy. That is exactly what country singer Miranda Lambert to then-husband Blake Shelton, Grammy Award-winning country singer. The two first worked together when they performed “You’re The Reason God Made Oklahoma” during CMT’s 100 Greatest Duets concert back in 2005. Since then, sparks were flying for the pair, and later on the two got married in 2011, five years after Blake and Kaynette split back in 2006. Unfortunately, Blake and Miranda split in 2015 amid rumors about her cheating on Blake. Today, Miranda is with singer Anderson East, and Blake is now with No Doubt frontwoman Gwen Stefani.
2. Brittany Kerr
While most on the list are celebrities who used to be mistresses and Ryan Shawhughes is a mistress of a celebrity, Brittany Kerr is a bit of an in-between. She’s an American Idol contestant, making her a bit of a celebrity. At the same time, let’s be honest: she’s not very well-known, making her not so much of a celebrity as others on the list. More to the point, it was country singer Jason Aldean—famous for surviving the Las Vegas shooting—who had her as his other girl. Previously, Jason was married to his high school sweetheart Jessica Ussery, until he was caught kissing Brittany back in 2012. A few months after the incident, he filed for divorce and started dating Brittany. In 2015, they finally got married.
1. Patti Scialfa
Patti Scialfa met Bruce Springsteen in the early ’80s in a bar in New Jersey before The Boss’s musical career took off. The two almost became a couple after she joined Bruce’s band The E Street Band, until Bruce got introduced to model and actress Julianne Philips, whom he married in 1985. In the same year, Bruce wrote his next album Tunnel of Love, which was mostly about his unhappy marriage. In 1988, he had the Tunnel of Love Express tour with Patti, where the two fell further in love. And when Bruce and Julianne split, the bad timing of it all drew negative press to the two. Despite all that, the two were perfect for each other and as of today they’ve been together for 26 years.
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