18 Most Bitter Breakups in Hollywood History

Some breakups are pretty amicable and the two parties remain friends.

Then there"s the ones that just don"t go down well and both parties throw jabs at one another on social media. 

It can get pretty tiring. 

We"ve compiled a list of some of the most bitter celebrity breakups in Hollywood history below:

1. Taylor Swift & Calvin Harris

Their breakup was a shocker and it obviously hurt Calvin just how quickly she moved on from him with Tom Hiddleston.

2. Johnny Depp & Amber Heard

This relationship came to a conclusion when Johnny allegedly struck Amber with a cell phone.

3. Kailyn Lory & Javi Marroquin

There were constant arguments between this couple on Teen Mom 2, but Javi being deployed seemed to be the final straw.

4. Madonna & Sean Penn

You know your relationship isn’t going well when there’s a nickname for it. The Poison Penns was a hilarious one.

5. Matt Damon & Minnie Driver

Remember Matt Damon announced in an interview that he was single and he failed to let Minnie Driver know? Talk about awkward.

6. Kim Kardashian & Kris Humphries

After a 72-day marriage, Kris Humphries felt that Kim had exploited their relationship for money and ratings. Was he right?

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18 Celebrity Break-Ups We Did NOT See Coming

We find it very difficult to talk about the following celebrity break-ups.

We"re still in shock that they happened. We"re still wishing the stars at the center of them give it another go with one another. But we"re not hopeful.

Here is a rundown of the splits that took us most aback when they went down…

1. Ian Somerhalder and Nina Dobrev

Did you ever see these two back when they were dating and promoting The Vampire Diaries together? It was like they were the only people in the room. We still can’t believe Ian married someone else.

2. Demi Lovato and Wilmer Valderrama

They were together for six years! They packed on the PDA on social media! They talked marriage mere weeks before their demise. We remain stunned.

3. Taylor Swift and Calvin Harris

They made it work for 15 months. That’s a very long time for Swift. We really thought she had found The One.

4. Robert Pattinson and Kristen Stewart

The most shocking cheating scandal in Hollywood history? Maybe, right? Stewart put the stunning nail in the coffin of this relationship when she made out with director Rupert Sanders.

5. Jon Hamm and Jennifer Westfeldt

They never married. But they were together for 18 years and they barely made any gossip pages during that time.

6. Kim Kardashian and Reggie Bush

It’s easy to forget now, what with the whole Kanye thing, but Kim and Reggie seemed totally in love back in the day. He seemed like the perfect man for the sex tape star.

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Kardashian Breakups and Makeups: A Romantic Rewind

Some Kardashian and Jenner family members have found true love.

Others are still looking.

As we outline below, however, one thing is certain: nearly all these reality star relatives have dated (and sometimes married!) around quite often in their quest for eternal happiness…

1. Damon Thomas

It’s true! Kim Kardashian was married to this music producer way back in the day! They were wed in 2004 and divorced in 2004.

2. RAY J!

Sorry. We always get excited about him. He dated Kim from 2004-2006 and made a sex tape with her that you may or may not have watched… 129 times.

3. Nick Lachey

Yup, before he took Jessica Simpson’s virginity, Lachey took a romantic chance on a then-relatively-unknown Kim Kardashian in 2006.

4. Nick Cannon

Cannon dated Kim from September 2006 through January 2007 and says the relationship ended because Kim lied about the existence of her sex tape.

5. Reggie Bush

Ah, the Bush and the Tush. Kim and Reggie dated from 2007-2010 and it really did seem like the professional running back would be The One. Alas.

6. Kris Humphries

The union may have only lasted 72 days, but it did exist. Kim really did marry this professional basketball player in 2011.

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Kylie Jenner: Singing About Breakups & Cheating on Snapchat!

When I was a teenager, if you wanted to give your ex a message, you"d tell a friend or stick a note on his car.

These days, the kids do it passive-aggressively on social media.

Fresh off her breakup with Tyga, Kylie Jenner is seemingly sending a message to her ex through song on Snapchat.

The lip kit maven posted a video of herself lip syncing to Beyonce"s "Hold Up," a new track from "Lemonade," which we know is all about cheating.

"They used to hide from you, lie to you," she mouthed to camera through a kooky green-faced filter.

It"s not the first or even thousandth time Kylie has sung to Snapchat, but this particular song choice in the wake of a breakup is telling, if not a classic adolescent move.

She went on to faux-perform another diddy about infidelity, this time through a zebra filter and crooning to "Losin" Control" by Russ.

“Should’ve ended it before it started. All she ever got was brokenhearted," she sang in the video, posted below.

"He was cheating on her, tryna flip it back on her like a victim.”

So, is she saying Tyga cheated on her?

Because lord knows there were a gazillion rumors suggesting just that.

Kylie hasn"t spoken publicly about the split, which was confirmed earlier this week.

However, a source told TMZ that Kylie and Tyga broke up because the two had different goals and wound up fighting about everything.

Tyga talked to reporters about the relationship twice this week.

He broke his silence by stating that he was doing "good" post-breakup and just trying to work and "evolve."

Then yesterday, he told paparazzi that he will always love Kylie, adding that "sometimes things just don"t work out."

 

Celebrity Breakups of 2016: Who Entered Splitsville?

Break out the violins, people!

The following famous couples gave their relationships a good run. But they simply could not make them work in the end.

Which split took you by the greatest surprise?

1. Kylie Jenner and Tyga

They dated for two years, with a few bumps along the way. But it all finally came to a head prior to the MET Gala in May, with sources saying the split was not amicable.

2. Kailyn Lowry and Javi Marroquin

Kailyn Lowry and Javi Marroquin seemed happy together… sometimes. But the Teen Mom confirmed their split on social media in early 2016.

3. Leah Messer and T.R. Dues

Another Teen Mom tragedy. These two were only together for a few months. But it still hurts.

4. Drew Barrymore and Will Kopelman

After four years of marriage and two kids together, Drew Barrymore and Will Kopelman went their separate ways.

5. Rose McGowan and Davey Detail

Rose McGowan filed for divorce from Davey Detail. The couple had been married for about two years.

6. Lea Michele and Matthew Paetz

Michele moved on to Paetz a couple years after Cory Monteith passed away. After splitting from him, she started dating Robert Buckley in the spring.

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Celebrity Breakups of 2015: The Year of the Split!

Plenty of celebrities broke up in 2015, as they do every year.

But this year … this was a year that produced some truly noteworthy splits. For a time, it was like you couldn"t go a week without one.

Heck, it wasn"t even like that, it was that. It was incredible.

Some couples were more high-profile than others, of course, and some romances felt destined to last forever while others … did not.

But man alive, this year was a doozy. Let"s take a look back …

1. Ben Affleck and Jennifer Garner

Ben Affleck and Jennifer Garner announced they were divorcing nearly 10 years after they got married. Rumors of their split have surfaced for months and were eventually confirmed … along with a firestorm of rumors that Ben slept with family nanny Christine Ounouzian.

2. Blake Shelton and Miranda Lambert

This one was pretty epic. Blake Shelton and Miranda Lambert broke up after four years of marriage – and their divorce was already final by the time they announced it. Short and sweet, right? Wrong. Myriad cheating allegations and no small amount of bitterness followed, along with his abrupt rebound romance with …

3. Gwen Stefani and Gavin Rossdale

Gwen Stefani and Gavin Rossdale were married for 13 years before parting ways in August 2015. Almost immediately, she took up with Blake Shelton while Gavin, like Ben Affleck, was linked to the nanny. Note to female celebrities: Don’t hire attractive 25-year-old nannies. Or just divorce these a– hats now if you’re particularly worried about this.

4. Zayn Malik and Perrie Edwards

So much for this sweet kiss. Zayn broke Perrie’s heart and called off their engaged in July … right around the time he broke up with One Direction no less. He’s since moved on with Gigi Hadid. Will he upgrade musically as well? (Sorry Perrie.)

5. Big Sean and Ariana Grande

We admit being a little sad about this one. The public declarations of love after their friendship led to so much more from mid-2014 to mid-2015 gave us real hope for these two … but the breakup was swift and a little contentious. Gotta “Focus” on careers? We’re not buying it.

6. Karrueche Tran and Chris Brown

Yes, they split up before, but it looks like this one is for good. That’s what happens when you’re revealed to be the father of a nine-month old, unbeknownst to your “bae.” Vintage Chris Brown.

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