The 20 Most Scandalous Hollywood Hookups

Love is a beautiful thing but sometimes it's also scandalous as these couples prove!

Brad Pitt and Angelina Jolie are one of Hollywood’s most scandalous hookups ever! The couple met on the set of Mr. And Mrs. Smith, when Brad was still married to Jennifer Aniston. Rumors of their on-and-off screen chemistry started floating around Hollywood, and though they both denied anything more than a professional relationship, it wasn’t long after Brad and Jen announced their divorce that Brad was snapped frolicking on the beach in Africa with Angie and her son Maddox.

But Brad Pitt wasn’t Angelina Jolie’s first scandalous romance! When the actress first hooked up with former husband Billy Bob Thornton, he was previously engaged to Laura Dern. “I left our home to go and make a movie and while I was away, my boyfriend got married and I never heard from him again,” Dern said about the bizarre love triangle.

Jennifer Aniston successfully maintained a good girl reputation in Hollywood, until she fell for her Wanderlust costar Justin Theroux, who was reportedly living with his stylist girlfriend Heidi Bivens at the time. Justin and Heidi quickly split, and although the fashionista remained tight-lipped about the incident, Jen was accused of being a home wrecker.

Tiger Woods shed his squeaky clean image of the picture perfect husband when his affair with New York party girl Rachel Uchitel was revealed. Several other mistresses came forward in the aftermath of the scandal, leaving his now ex-wife Elin Nordegren in utter shock.

Jesse James didn’t waste much time moving on after his cheating scandal destroyed his marriage to Sandra Bullock, getting into a romance with Kat Von D. Needless to say, the leopard didn't change his spots, and the tattoo princess and the motorcycle man never made it to the altar due to his philandering ways.

Age wasn’t an issue for The Green Mile star Doug Hutchison, who fell for 16-year-old Courtney Stodden when he was 51 and married the blonde bombshell in Las Vegas. Instead of keeping a low profile with their love, the couple flaunted it all over the media and have even starred on the reality show Couple’s Therapy.

Heidi Klum and Seal seemed totally in love, renewing their wedding vows every year, so it came a surprise when they suddenly split. It wasn’t long before Klum was linked to her totally hot bodyguard Martin Kristen, who she recently traded gold rings with.

On the hit show Smash, Debra Messing’s character cheats on her husband with Will Chase’s character. Reports say that life imitated art with the onscreen lovers, and that the Will and Grace star left her husband of several years for her hunky costar.

Britney Spears is no stranger to scandal when it comes to her love life, but the pop star went to the extreme when she started a less-than-professional relationship with paparazzo Adnan Ghalib.

Claire Danes has always kept a low profile when it comes to her love life, but she got a lot of heat in 2003 when Billy Crudup left his longtime girlfriend, Mary-Louise Parker, who was pregnant with their child, and immediately started dating Danes. They continued their scandalous romance for three years before both of them moved on.

LeAnn Rimes was a country star with a squeaky clean reputation until she cheated on her husband Dean Shermet with her married costar Eddie Cibrian. LeAnn soon left Dean and Eddie left his wife and the mother of his two kids, Brandi Glanville, and the couple went on to get married after both their divorces were finalized.

Though Jon Gosselin swears he didn’t cheat on Kate with Deanna Hummel, shortly after their marriage broke up he hooked up with his former wife’s plastic surgeon’s daughter, Hailey Glassman.

Woody Allen took scandal to the extreme, when he hooked up with his former partner, Mia Farrow’s, adopted daughter Soon-Yi Previn. They are still together 20 years later, and even have a child.

Heather Locklear and Richie Sambora called it quits after twelve years of marriage in 2007, and her close friend and neighbor Denise Richards didn’t waste any time before moving in on the Bon Jovi rocker. Months after the split, Denise, who was in the midst of a divorce herself, was already romancing Sambora.

Meg Ryan and Dennis Quaid appeared to be happily married for nine years, but their union was rocked when Meg met Aussie actor Russell Crowe on the set of the 2000 film Proof of Life. After announcing their separation, Ryan and Crowe went public with their romance, which fizzled shortly after.

Jude Law and Sienna Miller were one of Hollywood’s most beautiful couples, but after getting engaged, Law was caught red-handed cheating on his gorgeous fiancée with his nanny! Sienna later forgave him and they got back together, but the duo never made it to I Do.

Ashton Kutcher and Demi Moore’s marriage was rocked when the cub was caught hooking up with San Diego waitress Sara Leal, leaving his cougar wife devastated. The couple soon split, and while Kutcher moved on to his sexy That 70s Show costar Mila Kunis quite quickly, Moore went on a downward spiral and ended up in a treatment center.

Kristen Stewart and Robert Pattinson were young Hollywood’s most treasured couple, until Kristen was caught hooking up with her marriedSnow White and the Huntsman director Rupert Sanders! Though Robsten managed to patch things up, Sanders and his wife Liberty Ross are going through with adivorce.

The world was stunned when Ethan Hawke divorced his gorgeous wife Uma Thurman, but even more so when he started dating his nanny Ryan Shawhughes, who he was rumored to have been cheating with. It wasn’t long before Ethan and Shawhughes started making babies of their own and headed to the altar.

Don’t date your friend’s former boyfriend unless you want to make things awkward! After Kate Hudson dated baseball stud Alex Rodriguez in 2009, Cameron Diaz scooped up her sloppy seconds and Kate was less than pleased about the pairing. Years later, the friends have managed to patch things up.