The Kardashians have built their brand and made their living by shocking the world — and their viewers — with their tactics, life decisions, and attitudes. That’s what Keeping Up With the Kardashians is all about, isn’t it? They’re supposedly living their normal lives and we’re watching them, but in reality, their “normal” is quite outrageous to the regular person. Narrowing this list down to just nine moments wasn’t easy, but we did it.
1. Kim Kardashian and Kanye West — The Grand Divorce
Kim and Kanye were an unusual couple, but somehow, they seemed like a perfect match. Remember when Kanye proposed at a stadium and all their friends and family were secretly waiting to celebrate with them? It was the stuff of fairytales.
They married in 2014 and quickly became the ultimate power couple — eccentric, stylish, and madly in love. That’s why it came as such a shock when the relationship fell apart. What looked like a modern royal romance ended in one of Hollywood’s most publicized divorces.
2. Khloé Kardashian’s Transformation (Style, Face & All)
Khloé has always been open about her transformation — or shall we say, her self-improvement journey. Over the years and seasons of KUWTK, everything about her evolved: her hair, face, body, fashion sense, and confidence.
But this wasn’t just about cosmetic tweaks or gym hours; it was personal growth. Khloé went from being the funny side character to a confident, business-savvy woman and a central figure in the Kardashian empire.
3. Kylie Jenner Becomes the World’s Youngest “Self-Made” Billionaire
Considering Kylie is the youngest of the Kardashian-Jenner sisters, it was a shock when Forbes announced that she was a “self-made billionaire” at just 21. We all knew her Lip Kits were popular, but a billion-dollar valuation? That was wild.
Then came the twist — Forbes retracted the claim after reviewing the numbers, saying she wasn’t quite a billionaire after all. What was more shocking: the overstatement or the very public correction? Hard to say.
4. Kylie Jenner’s Secret Pregnancy and the Stormi Reveal
The Kardashians aren’t known for keeping secrets — quite the opposite, actually. But Kylie managed to pull off the impossible: an entire secret pregnancy.
For nine months, she went completely radio silent — no KUWTK mentions, no paparazzi leaks, not even a rumor that stuck. Then, in 2018, she revealed she’d given birth to her daughter Stormi with a YouTube video titled “To Our Daughter.” The internet collectively lost its mind.
5. Tristan Thompson Cheats on Khloé Twice (and Then Some)
Relationship drama is nothing new in the Kardashian universe, but Khloé’s story with Tristan Thompson truly shocked fans. It was just so cruel and public.
Here’s the timeline:
- April 2018: News breaks that Tristan cheated on Khloé while she was nine months pregnant with their daughter, True.
- February 2019: He’s accused of hooking up with Kylie’s then–best friend, Jordyn Woods.
- 2021: He admits to fathering another child while still with Khloé.
How she stayed so composed through it all remains one of life’s great mysteries.
6. Caitlyn Jenner’s Transition (Two Years After Divorce from Kris)
In 2015, Caitlyn Jenner publicly came out as transgender, just two years after separating from Kris Jenner. It was a historic moment that not only changed the family dynamic but became one of the most-discussed cultural shifts of the decade.
Caitlyn’s transition was both deeply personal and intensely public, sparking conversations worldwide about identity, courage, and acceptance.
7. Kim’s Paris Robbery — Fear & Fame Collide
In October 2016, Kim Kardashian’s life changed forever when she was held at gunpoint in her Paris hotel suite and robbed of millions in jewelry.
The terrifying ordeal forced Kim to reevaluate her relationship with fame and security. It was one of the few times the public saw her stripped of her glamorous armor — a chilling reminder that even the most famous woman on the planet isn’t untouchable.
8. Kourtney Kardashian Pulls Out Son Mason During Labour on KUWTK
In 2009, Kourtney Kardashian gave the world one of the most unfiltered reality-TV moments ever. She allowed cameras into the delivery room — and didn’t just show her face during labor. She literally pulled out her baby, Mason Disick, with her own hands on camera.
It was raw, shocking, and oddly beautiful. Half the viewers gasped, the other half applauded her calm composure mid-delivery. Either way, no one forgot that scene.
9. The End of an Era: The Kardashian-Jenners Announce the End of KUWTK
On September 8, 2020, the family announced that after 20 seasons and 14 years, Keeping Up With the Kardashians would end in early 2021. Cue the tears, nostalgia, and dramatic goodbyes.
But of course, in true Kardashian fashion, it wasn’t really the end — just a rebrand. They moved networks, launched The Kardashians on Hulu, and continued to dominate pop culture. Some things never change.
