The 29 most chaotic Keeping Up With The Kardashians moments ever

Remember when Kim found a girl in Scott’s hotel room?

3 years ago

The final season of Keeping Up With The Kardashians is finally here and after nearly 20 seasons there have been a LOT of dramatic moments.

Since the show began in 2007 we’ve seen the Kardashian and Jenner sisters evolve from unknown reality stars to full on millionaires with thriving businesses and lives that are never out of the press. On the show we’ve seen more babies born on TV than in One Born Every Minute, countless weddings, endless arguments and of course a few fuck ups.

There have been so many chaotic moments in the past 19 seasons it’s hard to mention every shocking moment, however we’ve rounded up the most unforgettable, wild and heartbreaking moments from 14 years of Keeping Up With The Kardashians.

These are the 29 most dramatic Kardashian moments ever:

Kim poses for Playboy

One of the earliest iconic Kardashian moments happened in season one when Kim posed for Playboy. Like any good mother Kris Jenner was right there to support her taking her own photos and saying the now iconic line “you’re doing amazing sweetie”.

Whilst not groundbreaking at the time, we have to thank it now for all the memes it’s given us since.

Kim hits Khloé with her bag

The Kardashian sisters just excel at fighting with each other and this moment in season two was an early classic.

Kim and Khloé had an argument over a Bentley that no one really remembers but what we all remember is Kim hitting Khloé with her bag and saying “don’t be fucking rude”. What a classic.

Khloé going to jail

All the best lines from the show came from the first couple of seasons. At the beginning of season three Khloé is driven off to jail for a day after violating her probation for her DUI.

The whole family really came together to drive Khloé to jail, well except Kim who was too busy taking photos of herself, causing Kris to say the memorable line “Kim would you stop taking pictures of yourself your sister’s going to jail.”

Khloé gets married to Lamar after a month of dating

Khloé always has the most chaotic storylines of the sisters. In season four she married Lamar Odom after dating for a month.

The wedding was a quick turn around, everyone was in shock, but for a few years they really were a great couple.

The trip to Las Vegas when Scott shoves a $100 bill down a waiter’s throat

Is there ever a series that goes by without Scott doing something chaotic? Probably not.

In one episode the family makes a trip to Las Vegas for Kim’s birthday. Scott gets completely drunk and obviously Kris tells the waiter not to serve him anymore drinks. Scott does not listen to this and proceeds to shove a $100 bill in the waiter’s throat. He really is charming.

Mason is born on camera

In what became an odd Kardashian tradition we saw the first of many babies being born on screen, as in literally Mason being pulled out of Kourtney.

Scott punching a mirror

Technically this moment happened in Kim and Kourtney take Miami, but it’s unforgettable so has to be included.

This really was the time when Scott was at his lowest and in one episode he gets so drunk he ends up punching a mirror.

Kim loses her earring in the ocean

“Kim there’s people that are dying” came from Kourtney in a 2011 episode of Keeping Up With The Kardashians.

They’re all in Bora Bora, Kris Humphries throws Kim in the ocean and she loses her earring, cries and Kourtney delivers her epic line.

Kim gets divorced after 72 days of marriage

After the cringiest proposal and most extra wedding Kim and Kris Humphries decided to divorce after a whole 72 days of marriage.

Kim gives birth to North

The first of Kim and Kanye’s children North was born in 2013 and throughout the season we saw how much Kim struggled with her pregnancy. It’s not really iconic or chaotic but it’s just nice and I want to celebrate it.

Kanye’s proposal

Look we all know Kanye does things on another level and his proposal to Kim was no exception. In fact it was a two part special for the show.

He proposed in a baseball field whilst an orchestra was playing a Lana Del Rey song in front of all Kim’s friends and family. Guys if you’re reading, this is how you do a proposal.

Rob doesn’t attend Kim’s wedding

Kim and Kanye’s wedding episode was full of beautiful Italian countryside, days out in Paris and of course drama.

The biggest scandal of the episode was Rob not attending Kim’s wedding because he didn’t want to be in the public eye.

Kris and Caitlyn get divorced

Kris and Caitlyn dragged their divorce out for a long time. They initially were separated with Caitlyn living in that beach house in Malibu.

But the couple eventually divorced in season 10.

Caitlyn’s transition

Also in 2015 was a moment that shocked us when Caitlyn announced she was transgender. The show dedicated a two episode special for Caitlyn to share with the family she was beginning her transition.

Kourtney and Scott break up

If ever there was a relationship that was more on and off it’s Scott and Kourtney. Throughout all 19 seasons we’ve seen them break up more times than I can count.

But they finally did breakup for good in 2015. Their relationship continued to bring plenty of drama even in the current season where the two are teasing getting back together 👀.

Kylie revealed she had lip fillers

Kylie is really good at keeping secrets. One of her most iconic ones was not revealing she had lip fillers done and instead just said she was over-lining her lipstick.

And it kinda worked, she launched the mega successful Kylie Cosmetics with her lip kits. On the show she explained in detail about why she got them done because of her insecurities.

Rob proposed to Blac Chyna and the girls find out on Instagram

Rob and Chyna’s relationship was a rollercoaster to say the least. It caused tension from the start on account of Chyna sharing a son with Tyga who was in a relationship with Kylie at the time.

And then after 10 weeks of dating the two were engaged. Kim, Khloé and Kourtney were filmed finding out whilst on a skiing holiday getting full glam. Truly iconic.

The Kanye and Taylor Swift saga

Though Kanye didn’t appear regularly on the show, his drama still managed to make it in. When Kanye released his song Famous which featured a line about Taylor Swift, Taylor claimed she had no idea she was going to be included in it.And then Kim released a recording of Taylor agreeing to the mention in a song.

The whole saga is then played out on Keeping Up With The Kardashians when Kris tells Kim to call Taylor up and sort it out, to which Kim gives a firm no to.

Kim robbed at gunpoint

Obviously this wasn’t on the show, but the immediate after effects of Kim being robbed at gun point whilst in Paris were. Whatever your opinions of the Kardashians are there is no way you can watch the episode without feeling emotional for Kim.

Kim found a woman in Scott’s hotel room

This scene should have won an Oscar, you could honestly cut the tension with a knife. When Scott and Kim were on a work trip to Dubai staying in the boujee Atlantis Hotel, Kim discovered a woman in Scott’s hotel room.

Everyone knows what’s going on, it’s like an insane witch hunt and the poor girl has to deal with Kim shouting through the bathroom door. But it is all worth it seeing Scott sweat so much.

Scott brought a woman to a different hotel in Costa Rica

No reality show is complete without a good glass of water chucking scene and that’s exactly what happened when Scott brought a girl on his family holiday to Costa Rica. Literally a few weeks after the Dubai trip.

At a nice family dinner the girls discover Scott actually has a girl staying in his hotel room whilst he’s hanging out with the family. Khloé, our lord and saviour, proceeds to throw a glass of water on him at dinner and it’s priceless.

Caitlyn’s memoir

After Kris and Caitlyn’s divorce and Caitlyn’s subsequent transition, there was a lot of tension in the Kardashian family, which only escalated when Caitlyn released a tell-all memoir.

One episode of the show featured the girls being upset Caitlyn didn’t tell them she had undergone gender reassignment surgery. Kim then went onto say she had received a copy of the book but believed it was an edited version.

Kim then dropped another bombshell when she revealed in Caitlyn’s book she had written she thought Rob Kardashian, the girls’ father, who defended O.J. Simpson, believed O.J. was guilty. Which Kim and her sisters were not happy with.

Kendall’s Pepsi advert

You know this one was coming. Who could forget Kendall doing that awful Pepsi advert where she hands protestors a can of Pepsi and magically saves the world?

She then cried on Keeping Up With The Kardashians about how she didn’t mean to upset anyone.

Kylie’s pregnancy

Truly the greatest kept secret of our generation. The actual reveal came before it aired on the show with Kylie’s video.

But it was still cool seeing the behind the scenes of when she finally revealed she had Stormi. Even if we didn’t get to see her being born.

Tristan cheated on Khloé as she was giving birth

For the hardcore Kardashian fans this episode was hard to watch. Khloé had such a rubbish time with men, finally found the one, was about to have their baby and then a video came out of Tristan kissing a girl.

We were all Kim and Malika trying not to get angry at Tristan in the delivery room, because Khloé was so calm and even though he had just cheated on her she still wanted him in the room when she gave birth to baby True.

Kim revealed she was on ecstasy whilst doing sex tape

I feel like this never got the attention it deserved. In a recent episode Kim causally mentioned she was doing ecstasy on the sex tape that made her famous.

Khloé discovers Tristan cheated again this time with Jordyn Woods

Honestly this was so chaotic. Longtime Kardashian fans know how much Jordyn Woods was a good mate of Kylie’s, so then to hear she had kissed Tristan at a party was shocking.

Kim and Kourtney found out about the rumours live on camera whilst Kim was filming her interviews. The whole episode was wild as it basically put an end to Jordyn and Kylie’s friendship.

The Kimono line

Another Kardashian mess up was caught on camera and this time it was epically bad. Kim named her shape-wear line “kimono” and it obviously got a lot of hate for using a culturally appropriate name.

The mayor of Kyoto even wrote Kim a letter explaining why the name was offensive. She apologised and changed the name to Skims and still managed to make millions.