The one thing all celebrity breakups have in common is that they are rarely quiet. Add to that a new partner, a confusing timeline, a few suspicious “we’re just friends” comments, and suddenly the whole hubbub becomes a feast for the tabloids.
Some of these relationships turned into solid marriages. Others were as fleeting as a Wi-Fi signal in an elevator. But regardless of that, here are some of the most famously controversial relationships where actors decided to switch to a newer model.
Eddie Cibrian and LeAnn Rimes
Eddie Cibrian and Brandi Glanville were married with two kids when he filmed Northern Lights with LeAnn Rimes in 2009. At the time, she was also in a relationship, which made the whole thing extra messy. At first, Cibrian was in full denial, but eventually, photos and reports started coming in, telling a very different story. Naturally, neither of the couples wanted to stay together, so both marriages ended. This also meant that Cibrian and Rimes could finally be together. Despite the 9-year age difference, they appear to be thriving.
Kelsey Grammer and Kayte Walsh
Kelsey Grammer dumped Camille Grammer around the time she was on The Real Housewives of Beverly Hills, but then he quickly moved on to courting Kayte Walsh, a British flight attendant more than 20 years younger than him. The couple got married just weeks after finalizing his divorce from Camille. That is not even long enough for a rebound, let alone a marriage. Camille didn’t seem to mind, as she received a huge settlement, and Kayte later admitted she was dating Kelsey while he was still married. Still, the marriage lasted, and they went on to have children together.
Billy Crudup and Claire Danes
Billy Crudup’s breakup with Mary-Louise Parker was quite scandalous because Parker was pregnant when he left. Instead of being a father, he chose to start a relationship with Claire Danes, his 24-year-old Stage Beauty co-star, and the whole thing became a tabloid nightmare. Danes later said she didn’t fully understand the consequences at the time, but that’s not an excuse. Despite lasting several years, Crudup and Danes’ relationship ultimately came to an end.
Ewan McGregor and Mary Elizabeth Winstead
Ewan McGregor had been married to Eve Mavrakis for more than two decades when he met Mary Elizabeth Winstead while working on Fargo. After McGregor was caught kissing Winstead, everything just went downhill for him. He claimed that his marriage was dead in the water, but that’s why you have this option called “divorce.” Granted, having a kid together would make it more awkward, but anything’s better than sneaking around with a young hottie. Eventually, McGregor and Winstead got married and had a child, but the past drama still lingers.
Ben Affleck and Lindsay Shookus
Ben Affleck and Jennifer Garner were once one of Hollywood’s most likable couples, but then they separated in 2015, and Affleck laid his eyes on the Saturday Night Live producer Lindsay Shookus. Their relationship did not last, and Affleck eventually returned to Jennifer Lopez (no, not Garner) years later. That marriage also ended, because, apparently, the Bennifer cinematic universe refuses to stop producing sequels.
Marilyn Manson and Evan Rachel Wood
Dita Von Teese’s marriage to Marilyn Manson ended after less than a year due to the artist’s fling with Evan Rachel Wood, who was only 19 at the time. This case is different from the others because Wood later publicly accused Manson of abuse. Manson denied those allegations and pursued legal action, though he eventually dropped the lawsuit. This story is less about the “messy celebrity romance” and more about scandals growing into something more serious than just rumors.
Johnny Depp and Amber Heard
Johnny Depp had been with Vanessa Paradis for 14 years when he met Amber Heard. In 2012, Depp and Paradis went their separate ways, and in 2015, Depp made one of the biggest mistakes of his life—he married Heard. This unholy union collapsed quickly, and the divorce became one of the most public, hostile celebrity breakups of the modern era. Then came the defamation trial, which turned private info and courtroom testimony into entertainment. The internet treated it like a sporting event, only in the end, there were no winners, as both of them had taken major hits to their public images and careers.
Jason Aldean and Brittany Kerr
Jason Aldean was married to his high-school sweetheart, Jessica Ussery, when he was spotted by the paparazzi flirting with Brittany Kerr, a former American Idol contestant. He claimed to be intoxicated and offered an apology, but it proved insufficient, leading to the collapse of their marriage. Aldean and Kerr later confirmed they were dating, then married in 2015. They now have children together and live a very lavish country-star lifestyle.
Brad Pitt and Angelina Jolie
Brad Pitt and Jennifer Aniston’s breakup remains one of the most talked-about celebrity splits ever, mostly because they met while filming Mr. & Mrs. Smith. Pitt and Jolie became a global power couple and eventually married. Then their own relationship ended in 2016, leading to years of legal fights. Their divorce dragged on for so long that it should have gotten its own HBO show. Pitt later moved on with Ines de Ramon, while Jolie has largely kept her love life private.
