16 Shocking 'Keeping Up With The Kardashians' Moments That Prove The Early Seasons Were Built Different

Keeping Up With The Kardashians mastered the art of keeping viewers on their toes.

Keeping Up With The Kardashians, the early seasons in particular, remind us about how the famous family became so ingrained in pop culture.

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From memeable moments to truly jaw-dropping, tear-jerking, heartbreaking life events, the Kardashian-Jenner clan has bared it all. Here are some moments we'll never forget.

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1. Kris' iconic "You're doing amazing sweetie" during Kim's Playboy photo shoot

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After encouraging Kim to model for Playboy, Kris takes the project home by providing vocal support on the set of the shoot.

2. Kim accidentally losing Kourtney's (underage) nudes that she stole as a prank

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Years prior to their reality show fame, Kourtney took naked photos with/for her high school boyfriend. Kim stole them as a prank and hid them in a purse in her home which was later stolen. After receiving news that someone is shopping the photos around, the famous family has to loop in the FBI.

3. When Kris sold Kim's calendar that she shot for Reggie

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Concerned she was letting a project slip through the cracks (something she did a few times that season), Kris gets her momager on and sells Kim's sexy calendar to be printed. The only problem is it was a private project for her then-boyfriend Reggie Bush, leaving Kim to scramble to get them off all the store shelves in LA.

4. Khloé's DWI (and Kim taking selfies on the way to drop her off at jail)

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The family was disappointed to hear Khloé Kardashian was arrested for a DWI, but tried taking a more humor-as-a-coping-mechanism approach to Khloé violating probation and being required to do jail time. And all the while, Kim was in her selfie bag as everyone cracked jokes.

5. When they tried hiding Khloé and Lamar's engagement from Caitlyn with wedding planners and Vera freaking Wang in their house.

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You could understand why Khloé wouldn't want to tell her stepdad about her engagement to her boyfriend of a few weeks, but the lengths nearly the whole family went to in order to keep the news from Caitlyn (who later found out while watching the evening news) were pretty ridiculous.

6. When Kourtney literally pulled her firstborn out of herself

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Seeing Kourtney's family watch in awe as she reached down and pulled her baby out of her own body was something truly surreal and a scene that's replayed in my head a thousand times since first seeing it. Just how?!

7. Kourtney squirting breast milk on Kim's psoriasis.

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Kim starts stealing tiny bits of breastmilk from Kourtney to treat a psoriasis flare-up, only for the new mom to direct deliver upon learning the news.

8. When Rob accidentally drank a Viagra-spiked drink Kris had made for Caitlyn

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Kris Jenner decides to have a little fun with Viagra by slipping some in her spouse's coffee, only to later learn Rob accidentally drank it and was worried something was wrong with him.

9. Scott punching the mirror in Miami

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Scott Disick's bad behavior has been well documented on the show, but nothing highlighted how much he was really struggling than to see him go on an angry, intoxicated rampage after Kourtney accused him of letting people smoke weed in the hotel room they were staying in with a then-baby Mason.

10. Kris shading Kim over her marriage to Kris Humphries (multiple times).

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The Kardashian-Jenner clan was pretty clear about thinking that the Kim-Kris Humphries relationship was destined to fail, but the way all of them (but particularly Kris) have brought it up is truly a masterclass in shade.

11. Kim hooking up with her bodyguard.

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Okay, so it was a former bodyguard, which makes it a little less juicy, but it's still behavior you wouldn't expect Kim Kardashian to engage in, let alone publicly admit. The fling with the Aussie didn't last but it made for a funny little arc on the show.

12. Scott attacking the waiter in Las Vegas

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After Kris instructs a waiter to cut Scott off while he was wasted at a family dinner, Scott takes it up with the waiter and ends up shoving money in the guy's mouth and telling him to STFU, which didn't go over well with anybody.

13. Khloé and Lamar's two-year divorce, which was paused after his near-death experience.

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Khloé's relationship with Lamar sadly didn't last, but no one anticipated that Lamar would OD and nearly lose his life, two years after the former couple's separation and in the final stages of their divorce, which Khloé put on hold to be able to help make his medical decisions. 

14. Caitlyn Jenner's transition, two years after her divorce from Kris

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Kris and Caitlyn's divorce wasn't a complete surprise to viewers, who watched the two's interests diverge over the years. Caitlyn's decision to publicly come out as trans and to physically transition caused a lot of turbulence for the family and changed some relationships within it forever.

15. Kim chasing a woman out of Scott's hotel room

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Scott's sneaking girls around put the last nail in the coffin of his relationship with Kourtney, and Kim, being the ride or die she is, confronted one of them when she busted Scott in Dubai.

16. The aftermath of Kim being robbed at gunpoint in Paris, including the suggestion she faked it for attention

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The world was shocked by news that Kim was robbed at gunpoint in Paris in 2016. KUWTK ditched their polished filming look in favor of home video which captures the aftermath and Kim's emotional state, from her fighting back tears as she prepared to reunite with her kids to her sobbing as she tells her sisters she thought she wouldn't survive.

What Kardashians moments stuck out in your head as the most outrageous? How much of it felt like it put the "real" in "reality"? Talk about it in the comments.