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When Kim Lost Her $75,000 Diamond Earring in The Ocean
2 of 14
When Kim Stripped Down For Playboy
Kris was on board from the start, but Kim wasn't so sure about posing for Playboy so soon after the negative publicity around her leaked sex tape. Ultimately, she agreed to be shot semi-nude with pearls draped all around her body, giving us a memorable December 2007 cover and one of the greatest Kris Jenner memes of our time.
"I mean I'm sure she's not just standing there with her boobs out," Kourtney said to Khloé while Kim was at the shoot. Nope, because she saved that for Paper magazine!
3 of 14
When Kris Got Really Drunk and Tattooed Kendall and Kylie's Names on Her Back
Someone plays favorites! While Kim fought with Kourtney and Khloé over ruining her "Bentley moment," Kris got drunk with one of her friends and decided to tattoo her lower back with Kendall and Kylie's names flanking a cross.
"Well, I'm mad at Kim and Kourtney and Khloé, so I'll just do Kendall and Kylie," she said. Wait a second, what about Rob?!
4 of 14
When Khloé Would Rather Go Naked Than Wear Fur
Kim isn't the only Kardashian sister to bare it all -- Khloé had her own nude shoot during season three when she starred in a campaign photo for Peta's "I'd Rather Go Naked Than Wear Fur" initiative. Since then, the star has disaffiliated herself from the organization after Peta anti-fur protesters pelted Kim with a flour bomb in 2012.
5 of 14
When The Sisters Did Their First Swimsuit Shoot Together at Joe Francis' House
The sisters (and Kris, duh) jet off to Puerto Vallarta for an Ashley Paige swim shoot at Girls Gone Wild creator Joe Francis' house without telling Caitlyn. Caitlyn flies down to Mexico, crashes the shoot and drama ensues. Oh, and of course Kris pops in for a few shots, because why not. Classic season one antics on KUWTK!
6 of 14
When Kim Cried Over Her Semi-Nude W Magazine Shoot
Long before Kim bared it all on the cover of Paper magazine, her W magazine cover (portraying the star nude in a pool of silver paint) caused tears on season one of Kourtney and Kim Take New York. "I'm so f—king mad right now!" she sobbed on the phone to her momager Kris Jenner. “[They] promised me I would be covered in artwork on top of me. It was so uncomfortable. I'm really honestly freaking out."
7 of 14
When Kylie Got in Trouble For Wearing Too Much Makeup
Before she built her $1 billion Kylie Cosmetics empire, Kylie was just your average 11-year-old girl experimenting with makeup. But as the youngest child in the family, Kylie's dad wasn't having it. When Kylie showed up to dinner with a full smoky eye, heavy liner and red lipstick, her dad freaked. "She's dressed like a 30-year-old and eating like an 11-year-old," Caitlyn said.
"You gotta deal with your kids growing older," Kris replied. "No. She's 11 years old and she shouldn't be wearing all that makeup and she shouldn't be wearing that outfit and that's the bottom line," Caitlyn said.
8 of 14
When Kim Started to Show Signs Of a Shopping Addiction
It got so bad, Kourtney and Kris took Kim to the mall and challenged her not to buy anything. But of course, Kim couldn't last one visit to Bloomingdales without making a purchase, and was caught red-handed sneaking back into the dressing room to buy clothes.
"I am adult. I can do whatever I want!" she said when her mom and sister busted her. "That's what an addict would say," Kris replied.
9 of 14
When Half of Kourtney's Face Froze
Kourtney wouldn't let a half-frozen face stop her from a good time. The star met Khloé for lunch after she got anesthesia at the dentist ... that didn't quite wear off in time. "What is that mug on your face?" Khloé laughed. "I can't really talk cause I had my face numbed," Kourtney replied.
10 of 14
When Kanye Cleaned Out Kim's Closet
When Kim started dating Kanye, the world noticed a major style change. Gone were the KUWTK star's leopard print looks, chunky belts and curve-accentuating bodycon dresses, thanks to the help of the Yeezy designer and his stylist.
11 of 14
When Kendall Snuck Off To Vegas And Almost Got a Tattoo
For her sweet sixteen, the soon-to-be-supermodel headed to Vegas with Kylie to get a tattoo without her parent's permission. But once she got in the chair, Kendall started having second thoughts and called Kourtney, who eventually talked her out of it.
"I know it’s exciting to do something so you can show everyone. That’s what I did when I got my boobs done. Afterwards, I regretted it so much,” Kourtney told her over the phone. “It’s a tattoo. It’s there forever.”
12 of 14
When Kris Forgot About Kourtney's First Cover Shoot
Kris got so caught up with Kim's exciting appearance at Comic Con for her role in Disaster Movie, the momager forgot about her eldest daughter's first magazine cover shoot for 944 magazine. Luckily, Khloé came to the rescue and cheered Kourtney on from the sidelines.
13 of 14
When Kim Got Psoriasis
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When Kim Took Selfies During The Car Ride to Drop Khloé Off at Jail
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