10+ Times Hollywood Couples Were Truly Chaotic

Making a relationship work in Hollywood isn't easy.

There is a lot of public scrutiny, with fans watching your every move. Things either go in an upward direction or they go south, fast.

Nine times out of ten, it's the latter. Ready for some craziness? Here are 10+ times Hollywood couples were truly chaotic!

1. Demi Moore and Ashton Kutcher

When the actress released her memoir, Inside Out, in 2019, a lot was revealed about her former high-profile marriage to Ashton Kutcher.

One thing that stood out is Ashton allegedly asking Demi for threesomes.

Engaging in these acts caused the *Ghost* actress a lot of shame, as well as leading her to believe that it's what caused Ashton to allegedly cheat twice during their marriage.

She also wrote that she blames him for breaking her 20 years of sobriety.


2. Johnny Depp and Amber Heard

Their 15-month marriage was filled with strife. After announcing their divorce, allegations of emotional and physical abuse were tossed from both sides.

For instance, Heard wrote in court documents that she "endured excessive emotional, verbal and physical abuse from Johnny."

3. Tori Spelling and Dean McDermott

Their relationship has been drama-filled since the very start.

That's because they were both married to other people when they got involved after meeting on the set of a Lifetime movie.

On Tori’s show, *True Tori*, she even revealed that she and Dean had sex the night they met.

As if that wasn't chaotic enough, Dean went on to cheat on Tori. When this happened, she saw it as karma.

4. Mel Gibson and Oksana Grigorieva

In 2010, audio obtained from RadarOnline was released of Gibson having a heated argument with his ex-girlfriend, Oksana Grigorieva.

In it, he launched into a racist and sexist rant against her.

Around that same time, a domestic violence dispute investigation on the couple had been opened by the Malibu Hills Police Department.

They were also dealing with a custody dispute over their daughter and a restraining order that Grigorieva filed against Gibson for allegedly striking her in the face.

5. Billy Bob Thornton and Angelina Jolie

Angelina's three-year marriage to Billy Bob can be summed up with one word: weird.

When they were together, they thought it would be "romantic" to slice their fingers and store each other's blood in vials around their necks...

6. Sandra Bullock and Jesse James

Back in 2010, reports surfaced that Bullock's husband at the time, Jesse James, had been cheating on her with not one, but five women.

A month later, Bullock divorced him and went on to adopt her first child.

7. Lindsay Lohan and Samantha Ronson

In case you forgot, Lindsay dated DJ Samantha Ronson for a while back in 2008.

After the relationship ended, Lindsay later called it "toxic." She also issued out several disparaging tweets against Sam and her family.

8. Khloé Kardashian and Tristan Thompson

There has been a lot of Kardashian drama over the years, but this one really takes the cake.

In 2018, it was revealed that Khloé found out about Tristan cheating on her just two days before she gave birth to their daughter, True.

Sadly, that wasn't all.

A year later, Thompson was accused of cheating on Khloé with none other than close family friend, Jordyn Woods.

This led Khloé to break up with Thompson while Kylie Jenner had a friend breakup with Jordyn.

9. John Mayer and Jessica Simpson

After dating in secret for a while, John offered up a little too much information by calling her "sexual napalm" during his 2010 Playboy interview.

“A woman and how they are in bed is not something that is ever talked about,” Simpson told People. “It was shocking.”

10. Woody Allen and Soon-Yi

This might be the weirdest love triangle yet. Soon-Yi is the adopted daughter of Mia Farrow, the director's ex.

The couple had been dating for 12 years when Farrow found naked photos of Yi in Woody's apartment.

11. Tom Cruise and Katie Holmes

Remember when Tom Cruise jumped on Oprah's couch over his love for Katie Holmes?

You can't stop a man in love! But sometimes, someone really should. While the pair eventually got married, they divorced a few years later.

12. Emma Roberts and Evan Peters

The former pair's relationship turned physical in July 2013. And not the good kind of physical.

When police arrived at the couple's hotel in Montreal, Evan had a bloody nose and a bite mark. This led to Roberts being arrested.

13. Kanye West and Kim Kardashian

Early in 2020, they both made headlines after Kanye tweeted that wife Kim and her family were trying to "lock him up" following his shocking comments made at a political rally.

These comments included how he had wanted to abort their daughter, North...

14. Miley Cyrus and Liam Hemsworth

Miley raised some eyebrows when she was spotted kissing a girl the same day her divorce to Liam Hemsworth was announced.

Then, as their divorce got underway, Miley's song, "Slide Away," led people to believe that Liam had addictions to drugs and alcohol.

15. Tom Cruise and Nicole Kidman

Nicole and Tom were once one of the most powerful couples in all of Hollywood. But after they both said "I do," their real troubles began.

While nothing has been confirmed, rumors have persisted that the Church of Scientology forced Tom to end the marriage after Nicole refused to join.

16. Ariana Grande and Pete Davidson

Pete Davidson has been open about his struggles with mental health and BPD. After Ariana and Pete's engagement was abruptly called off, the SNL mainstay began posting what many interpreted to be a suicidal threat.

Pete said that during his relationship with Ariana, he was the victim of cyber bullying.

He assured his fans that no matter how hard times got, he'd never be the one to end his own life. Since then, Pete continues to take things one day at a time.

17. Madonna and Sean Penn

Sean Penn has a reputation for being volatile. While he was married to Madonna, the tabloids began circulating a story that Penn tied his estranged wife to a chair and assaulted her with a baseball bat.

18. Renee Zellweger and Kenny Chesney

Kenny and Renee's turbulent marriage ended just four months after it began. Instead of a divorce, the couple chose to get an annulment and cited fraud.

This led many at the time to question Chesney's sexual orientation.

19. Pamela Anderson and Tommy Lee

You'd be hard-pressed to find a moment in the relationship timeline of Pam and Tommy Lee that wasn't rife with chaos and controversy.

The pinnacle of which came when the couple's infamous sex tape was leaked to the public.

20. Denise Richards and Charlie Sheen

Denise has accused Charlie of both emotional and physical abuse, and of being a compulsive gambler and an addict.

Charlie in-turn took to Twitter to call his ex-wife an [expletive] as well as a liar and dog thief.

21. Selena Gomez and Justin Bieber

Over the course of the six-year off-and-on relationship between Justin and Selena, there were allegations of cheating, a fake pregnancy, one trip to rehab, and god only knows what else.

Justin and Selena were easily one of the worst couples of the 2010s.

22. Jessica Simpson and Nick Lachey

While watching their short-lived reality TV show, Newlyweds: Nick & Jessica, fans started to see early on that the binds of love and happiness were starting to unravel.

After three seasons, the show was canceled — as was their marriage.

23. Ozzy and Sharon Osbourne

In more than 34 years of marriage, Ozzy and Sharon have been through everything from substance addiction to physical abuse and infidelity.

The couple split up briefly in 2016 but have since reunited and are determined to make their marriage work.

25. Jack Nicholson and Anjelica Huston

Jack and Anjelica were together for 17 years. For their entire relationship, Nicholson was unapologetically cheating on Anjelica.

He wound up getting another woman pregnant, which led Anjelica to physically attack him one day while on set.

26. Courtney Love and Kurt Cobain

There are many people who believe that Kurt Cobain didn't kill himself. A popular conspiracy theory suggests that the suicide was a ruse to conceal the fact that Courtney herself had killed him.

These two were the '90s version of Sid and Nancy.

27. Jay-Z and Beyoncé

Solange Knowles is living proof that blood is thicker than water. When the news broke of Jay's alleged affair, Solange went to bat for her older sister.

She brutally assaulted Jay while the two of them were in an elevator.

28. Nic Cage and Erika Koike

Nic and Erika's marriage sounds like something out of a National Lampoon film.

These two got so wildly drunk that they wound up at the altar standing across from one another. Their wedding was annulled just four days later.

29. Kevin Federline and Britney Spears

Just how chaotic was Britney and Kevin's relationship? So chaotic that they actually made a mini-series dubbed Chaotic about their relationship. It lasted five episodes before being swiftly taken off the air.

Sometimes life imitates art in the most ironic ways.