Sex On The Side: Hollywood’s Hottest Mistresses

Brad Pitt, in black, poses on the red carpet with Angelina Jolie who wears a silvery top.
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Feb. 6 2020, Updated 6:03 p.m. ET

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Affairs are so common these days, and Hollywood is no stranger to them. But who are the most famous celebrity mistresses ... the women who had affairs with married men and, in some cases, replaced the wife?

MORE: HOOKING UP WITH THE HELP: CELEBRITIES CAUGHT IN NANNY CHEATING SCANDALS

They come in all shapes and sizes. Gisele Bundchen supposedly moved in on Tom Brady when he was still with Bridget Moynahan. Ryan Shawhughes had an alleged affair with Ethan Hawke that wound up destroying his marriage to Uma Thurman.

MORE: WENDY SLAMS MISTRESSES AFTER CHEATING SCANDAL: 'THERE'S A HOT PLACE IN HELL FOR YOU!'

Dive into the gallery to see who slept with whom — and who was left to pick up the shattered pieces.

1. Rachel Uchitel/Tiger Woods.

Rachel Uchitel, in blue jeans, leather jacket, and beige top, gets into a car.
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It appears that Tiger Woods was cheating on then-wife Elin Nordegren with a series of women, one of whom was Rachel Uchitel. Nordegren found out when she discovered a lot of inappropriate text messages on Woods’ phone. “People have called me all sorts of names, but they don’t know me,” Uchitel said. Interestingly, after divorcing Woods, Nordegren dated a man who had had a prior business relationship with Uchitel.

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2. Miranda Lambert/Blake Shelton.

Blake Shelton, in a black suit, poses on the red carpet with Miranda Lambert who wears a black dress with pink trim.
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These two country stars had a relationship that was the stuff of Country music gold. Blake Shelton was married to Kaynette Williams when he sang a duet with Miranda Lambert at CMT’s 100 Greatest Duets concert in 2005, and the chemistry was too strong. Shelton divorced Williams a year later and married Lambert in 2011. Lambert said, “It was just like this draw to each other. It was just sort of this inevitable chemistry." That chemistry fizzled out and they divorced in 2015.

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3. Evan Rachel Wood/Marilyn Manson.

Marilyn Manson, in black, walks hand in hand with Evan Rachel Wood who wears a purple dress.
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Rocker Marilyn Manson was married to Dita Von Teese when he met Evan Rachel Wood in 2006. She was just 18, but the attraction was so strong that Manson divorced Von Teese the following year. Wood got engaged to Manson in 2010, but it ended a year later. “I was craving danger and excitement,” Wood told Us Weekly. “Then you’re demonized for figuring it out and getting messy. People would call me a whore when I walked down the street, and you can’t not be hurt by that.”

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4. Soon-Yi Previn/Woody Allen.

Soon-Yi Previn wears a black dress with gold accents and stands next to Woody Allen who wears beige pants, a white shirt, and olve jacket.
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Woody Allen’s relationship with Mia Farrow fell apart after a decade because of a younger woman. The person was Soon-Yi Previn, Farrow’s 21-year-old adopted daughter. Allen and Previn then married in 1997. Allen told NPR, “I've been married now for 20 years, and it's been good. I think that was probably the odd factor that I'm so much older than the girl I married. I'm 35 years older, and somehow, through no fault of mine or hers, the dynamic worked.”

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5. LeAnn Rimes/Eddie Cibrian.

LeAnn Rimes, in a leopard print top, poses alongside Eddie Cibrian and their two kids on the red carpet.
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Singer LeAnn Rimes allegedly began an affair with her costar Eddie Cibrian when they appeared together in the Lifetime movie Northern Lights in 2009. At the time, each was married to other people, but by 2011 they’d divorced their respective partners and married each other. Rimes said, "I take responsibility for everything I've done. I hate that people got hurt, but I don't regret the outcome."

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6. Gisele Bündchen/Tom Brady.

Tom Brady, in a black tux, hugs wife Giselle Bundchen who wears a patterned black dress.
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In December 2006, football starTom Brady broke up with actress Bridget Moynahan and began dating Gisele Bündchen — but not in that order. In February 2007, Moynahan announced she was pregnant with Brady’s first child, Jack Moynahan. Brady and Bündchen got married in 2009 and went on to have two children together. But surprisingly, it appears the two women now have a friendly relationship because, as Bündchen puts it, “I want him to have a great relationship with his mom because that's important, but I love him the same way as if he were mine."

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7. Angelina Jolie/Brad Pitt.

Brad Pitt, in black, poses on the red carpet with Angelina Jolie who wears a silvery top.
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Jennifer Aniston was very happily married to Brad Pitt until he met Angelina Jolie. Jolie moved in on Pitt and shortly after replaced Aniston. Pitt and Jolie have since separated.

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8. Ryan Shawhughes/Ethan Hawke.

Ethan Hawke, in a grey suit and white shirt, poses with Ryan Shawhughes who wears a green dress.
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Ethan Hawke was married to Uma Thurman and had children together. But the end of their relationship was inside their home with them. Ryan Shawhughes was the kids’ nanny. Now she is the caregiver and mother to children she and Hawke had together. They married a few years after Hawke and Thurman divorced.

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9. Alicia Keys/Swiss Beatz.

Alicia Keys wears a white jacket and glittery top and poses alongside Swizz Beatz, who wears a black suit, on the red carpet.
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Rapper and producer Swizz Beatz was married to singer Mashonda when they gave birth to their son. But shortly thereafter, Beatz struck up a relationship with Alicia Keys. That led to a divorce for Beatz (who later married Keys) and led Mashonda to write, "If you are reading this Alicia, let me start by saying, you know what you did. You know the role you played and you know how you contributed to the ending of my marriage. You know that I asked you to step back and let me handle my family issues. Issues that you helped to create.”

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10. Elizabeth Taylor/Eddie Fisher.

Eddie Fisher, in a black suit and blue tie, looks at photos alongside Elizabeth Taylor who wears a big black choker, a prominent diamond necklace, and a black dress.
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Back in the day, Eddie Fisher was married to Debbie Reynolds. They had two kids (including the late Carrie Fisher), and Elizabeth Taylor was amongst Reynolds’ best friends. So it was all that more shocking when Taylor stole Fisher away, ending the marriage. In 1964, Taylor left him for Richard Burton. Before her death Reynolds said, "I was just like Jennifer Aniston with Brad Pitt when he fell in love with Angelina Jolie."

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11. Julia Roberts/Danny Moder.

Juliet Roberts, in a black jacket, white shirt, and red tie, sits at a dinner table next to Danny Moder who wears black.
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In 2000, Julia Roberts was dating actor Benjamin Bratt when she signed up to shoot The Mexican with Brad Pitt. But she soon moved in on one of the cameramen, Danny Moder, who was married at the time. Both relationships exploded leaving Roberts and Moder married and with three kids together.

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12. Britney Spears/Kevin Federline.

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In 2004, Britney Spears had her eyes on her backup dancer, Kevin Federline. Federline was engaged to actress Shar Jackson, and they were expecting their second child. That wasn’t enough to keep them together though. Federline ended things with Jackson and married Spears later that same year. They had two children together but split in 2006.

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13. Patti Scialfa/Bruce Springsteen.

Bruce Springsteen, in a black suit, stands next to daughter Jessica who wears a black dress, and wife Patti Scialfa, who wears a white coat over a black top and white pants.
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Patti Scialfa joined Bruce Springsteen’s E Street Band in 1984, but even though it was alleged that they dated briefly, they were happy just making music together. Springsteen even married actress Julianne Phillips in 1985, but it didn’t last as he and Scialfa moved past just making music together on stage. The Boss and Scialfa married in 1991 and have had three kids together.

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14. Kayte Walsh/Kelsey Grammer.

Kelsey Grammer, in a black tux and white shirt, has his arm around Katye Walsh who wears a peach-colored dress on the red carpet.
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Actor Kelsey Grammer was married to ex-MTV dancer and Real Housewife Camille Grammer when he met British flight attendant Kayte Walsh. They had an affair for six months until Camille found out and filed for divorce. Just two weeks after that divorce was finalized, Kelsey Grammer married Walsh, and they now have three kids together.

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15. Brittany Kerr/Jason Aldean.

Jason Aldean, in cowboy hat, jacket and jeans, poses alongside Brittany Kerr who wears a white pant suit with golden embellishments.
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Country singer Jason Aldean embraced the country song lyric in style when he had an affair with a former American Idol contestant. He was married to his high school sweetheart, Jessica Ussery, and father of their two kids when he was shot kissing Brittany Kerr in a bar. The marriage imploded, and seven months later Aldean began publicly dating Kerr. They eventually married in 2015.

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