It seems like every relationship in Hollywood is dramatic. From partners stepping out and work schedules getting in the way to wild party habits, there’s a lot that can go wrong between a couple when their whole life is played out in the spotlight.
The 15 couples who made this list have all become known for their drama and toxicity. As much as these pairs may have loved each other at one point, most fans would agree they’re better off apart. While some of these couples remain on-again, off-again and are likely to reunite sometime in the future, for others it’s safe to say they’ve learned their lesson and have called it quits for good.
Keep reading to discover the worst Hollywood couples.
15 Khloe Kardashian & Lamar Odom
Khloe Kardashian’s only marriage was to Lamar Odom - and we can see why she wouldn’t be itching to walk down the aisle again.
The two got married after only a few months, and not only did Lamar have a serious substance problem but he’s admitted to stepping out on her with countless women. The couple divorced shortly after he was found unconscious in a brothel.
14 Chris Brown & Rihanna
Chris Brown and Rihanna seemed like the music industry’s perfect power couple - that is until one fateful night in 2009. The couple was on their way to the MTV Music Awards when Chris mistreated the singer.
RiRi even testified against him in court, which made fans even more surprised when they tried to give their romance another go a few years later.
13 Jenelle Evans & David Eason
For a brief time, Teen Mom 2 fans thought Jenelle Evans had finally found herself a stable, caring man in David Eason after years of baby daddy drama. Now that they’ve been married for two years, that façade has been broken.
Not only has Jenelle called 911 on her man, but he made headlines last month for taking the life of the family dog, which resulted in the custody of their children being taken away.
12 Selena Gomez & Justin Bieber
During their infamous on-again-off-again relationship, which lasted for over six years, Selena and Justin faced rumors of stepping out, trips to rehab, and even a fake story that she was pregnant with Justin’s baby.
Justin married his wife Hailey Baldwin only months after reconciling with Selena following her health issues. Despite The Biebs being off the market, some sources say the two still have feelings for each other.
11 Britney Spears & Kevin Federline
Fans knew the marriage wouldn’t end well between Britney Spears and her back-up dancer K-Fed when they wed after only a few short months together. And welcoming their sons back-to-back sure didn’t help.
The singer quickly went into a downward spiral, which climaxed with her damaging a paparazzi car and shaving her head. Kevin had full custody of their sons for a while.
10 Rob Kardashian & Blac Chyna
Fans were convinced that Blac Chyna only got with Rob Kardashian because her baby daddy was said to have left her to date Rob’s half-sister, Kylie Jenner. The two had a whirlwind relationship, as they got engaged within months and announced their pregnancy shortly afterward.
Rob went on a social media tirade after she moved out of their home. They’re still negotiating custody of their daughter, Dream.
9 Lindsay Lohan & Samantha Ronson
Lindsay Lohan dated Samantha Ronson during the height of her downfall. The couple seemed to reinforce their hard-partying ways and Lindsay sought treatment at various facilities during their relationship.
Their eventual 2009 break-up was filled with arguments, talk of stepping out, and even rumors about restraining orders.
8 Johnny Depp & Amber Heard
Many fans were surprised when Johnny Depp and Amber Heard rushed to the altar, despite him never marrying his ex-partner Vanessa Paradis during their two-decades-long romance.
However, the unlikely couple divorced in 2017 after Amber said that Johnny had mistreated her. Leaked court documents have since revealed the extent of that, and just confirmed how toxic this couple was.
7 Amy Winehouse & Blake Fielder-Civil
Amy Winehouse got with her future husband Blake Fielder-Civil as she was rising to fame. But unfortunately, the tumultuous couple only reinforced each other’s bad habits and substance issues (he’s admitted to introducing her to substances).
Though they were divorced at the time of her passing, Blake went on record claiming she was the love of his life - even though he’d already remarried and welcomed two children.
6 Eminem & Kim Mathers
Eminem and his ex-wife Kim Mathers were actually married twice, once from 1999 to 2001 and then briefly in 2006. It’s public knowledge that the two were not only disloyal to one another, but they also reinforced their bad habits and substance problems.
Eminem wrote the dark song “Kim” in which he describes what he wishes he could do to his ex.
5 Kourtney Kardashian & Scott Disick
It was no secret that Scott Disick had trouble remaining committed to Kourtney Kardashian during their decade-long romance - and that she had a problem with his hard-partying ways.
Kourtney eventually called things off for good after Scott went on another party binge weeks after the birth of their third child and photos of him getting cozy with other women surfaced.
4 Mel Gibson & Oksana Grigorieva
Fans were not impressed when Mel Gibson left his wife of 30 years (and the mother of his seven children) to pursue a relationship with the much younger Oksana Grigorieva, who became pregnant with their daughter shortly afterward.
However, things ended badly between the pair after Oksana released a recording of Mel speaking badly to both her and her mother.
3 Madonna & Sean Penn
It was practically another lifetime ago, but Madonna and Sean Penn had an unlikely marriage from 1985 to 1989. Things ended dramatically when reports surfaced that Sean had been treating the singer badly.
If this seems like the latest news, it's because Sean has denied the stories, while Madonna refuses to speak about her experiences.
2 Kurt Cobain & Courtney Love
The most toxic celebrity pairing of the '90s was between Nirvana’s Kurt Cobain and Courtney Love. Both seemed to be bad influences for each other. Things got worse after they welcomed their only daughter, Frances.
Even after Kurt took his life, Courtney struggled to maintain a relationship with her only child.
1 Pamela Anderson & Tommy Lee
Baywatch star Pamela Anderson was only married to Mötley Crüe’s Tommy Lee from 1995 to 1998, but during their brief union, things were less than ideal. Pam has said that her ex-husband mistreated her and their two sons, and that includes an incident involving a vicious dog.
These two were always better off alone, although they have maintained a friendship over the years.
Sources: Cheat Sheet, Ranker, Radar Online