They say you should never mix business with pleasure, and that phrase couldn't be more true in Hollywood. Quite a few of our favorite celebrity couples split after working together in film, television or music. In celebration of the 20th anniversary of "Eyes Wide Shut," which hit theaters on July 16, 1999, Wonderwall.com is taking a look back at Hollywood lovers who called it quits after working together, starting with the erotic film's stars, Nicole Kidman and Tom Cruise. The couple met making their first movie together, 1990's "Days of Thunder," and immediately hit it off. After marrying in 1990 and starring in 1992's "Far and Away," Tom and Nicole teamed up again for Stanley Kubrick's "Eyes Wide Shut." Less than two years later, however, Tom ended their decade-long marriage. Keep reading for more…
Angelina Jolie and Brad Pitt's chemistry jumped off the screen when they starred in "Mr. & Mrs. Smith" together in 2005. Unfortunately, the second time around didn't go so smoothly. Brad and Angie filmed 2015's "By the Sea," which Angelina also directed, right after marrying in 2014. The movie bombed at the box office and Angelina left Brad less than a year later.
Aw, young love. Miley Cyrus and Liam Hemsworth met on the set of "The Last Song" in 2009 and fell head over heels for each other. They were soon engaged but their relationship hit a rough patch and they called it quits in 2013 after nearly four years of dating. But they rekindled their love more than two years later and tied the knot in 2018.
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Love blossomed between Robert Pattinson and Kristen Stewart while the pair were filming the "Twilight" film series. After several years together and an unexpected cheating scandal — Kristen was photographed hooking up with one of her directors — the two parted ways in May 2013 just a few months after the release of their final film together, "The Twilight Saga: Breaking Dawn Part II."
Nicholas Hoult and Jennifer Lawrence found love on the set of 2011's "X-Men: First Class" and went on to work together in 2014's "X-Men: Days of Future Past" too. However, after wrapping their second "X-Men" flick, the couple broke up. They went on to become close friends and work together again in 2016's "X-Men: Apocalypse" and 2019's "Dark Phoenix."
Like their characters, Jess and Rory, "Gilmore Girls" co-stars Milo Ventimiglia and Alexis Bledel cozied up together in 2002. The lovebirds split in 2006 as the show was filming its final season but had no issue reuniting on screen in 2016's "Gilmore Girls: A Year in the Life."
Rihanna and Drake's relationship first made headlines in 2009 about a year before the release of their No. 1 hit "What's My Name." The duo went on to have an off-and-on romance over the years and record three chart-topping songs together, "Take Care," "Work" and "Too Good." Their romantic finally came to end in 2017. RiRi revealed in a 2018 Vogue interview that the two "don't have a friendship now, but we're not enemies either. It is what it is."
Rachel Bilson and Hayden Christensen "jumped" head first into a relationship after meeting on the set of "Jumper" in 2007. They went on to have a 10-year relationship and even got engaged. They welcomed daughter Briar Rose in 2014 and split in 2017.
Life imitated art when Al Pacino and Diane Keaton began dating while filming "The Godfather" in 1972. The couple saw one another romantically — and worked together — off and on throughout the '70s and '80s before finally calling it quits for good in 1990 after filming "The Godfather Part III."
Sparks flew when Sean Penn began directing Charlize Theron on the set of "The Last Face" in 2014. By the end of the year, the couple were reportedly engaged. They abruptly ended their romance in June 2015, however, one year after filming their drama flick.
Jennifer Lopez and Marc Anthony were Latin music's hottest couple during their seven-year marriage. The duo starred in the 2006 biopic "El Cantante" together, toured the world together and worked on J.Lo's fifth album, "Como Ama una Mujer," together. All that work wasn't enough to keep their marriage alive, however, and the pair split in 2011 and divorced in 2014.
Cameron Diaz and Justin Timberlake hit it off in 2003 and filmed "Shrek the Third" together in early 2006. By January 2007, they were through. They still, however, managed to remain good friends and filmed the comedy "Bad Teacher" together in 2011.
Ben Affleck and Gwyneth Paltrow began dating in late 1997 after developing a relationship on the set of "Shakespeare in Love." The couple broke up in 1999, only to rekindle their romance on the set of "Bounce." By the time the movie was released in 2000, the pair had split for good.
Chris Evans and Jenny Slate met on the set of "Gifted" in 2015 and soon fell in love. By the time the movie premiered in 2017, however, the couple had split. Chris later told People magazine that Jenny was his "favorite human" and the pair got back together briefly before breaking up again in 2018.
Vanessa Hudgens and Josh Hutcherson sparked a romance while filming "Journey 2: The Mysterious Island" in 2011 but their relationship was short-lived and the pair broke up in 2012. Nevertheless, Vanessa and Josh remained "really good friends," according to an interview they gave on the "Today" show.
Drew Barrymore and Justin Long hit it off in 2007 after connecting on the set of "He's Just Not That Into You." The pair broke up shortly after filming — only to get back together while filming "Going the Distance" in 2009. Drew and Justin ended things for good one year later.
Cher and Sonny Bono were one of Hollywood's most celebrated supercouples. Throughout the 1960s and '70s, the pair dated, married, welcomed a child together, starred in four television shows and specials together, appeared in two movies and released five albums together! Their romance eventually ran its course and they divorced in 1976.
Gwen Stefani began dating bassist Tony Kanal shortly after joining No Doubt in 1987. The bandmates-turned-lovers recorded three albums together, "No Doubt," "The Beacon Street Collection" and "Tragic Kingdom," before breaking up in 1994. Luckily, the two were still connected musically and went on to release three more albums with No Doubt. In fact, Gwen's 2004 hit "Cool" is about her friendship with Tony.
Dominic Sherwood and Sarah Hyland were a match made in heaven — that is, until they worked together. The duo began dating in 2015 and even got matching tattoos before Sarah guest starred on two episodes of Dominic's show, "Shadowhunters," in 2017. Within weeks of the episodes' release, Sarah and Dominic went their separate ways.
Lily Collins and Taylor Lautner sparked a romance on the set of "Abduction" in 2010 but their love only lasted a short while. The couple parted ways in 2011 just a few months before they launched a press tour for the action-thriller film.