Keeping Up with the Kardashians: 5 craziest KUWTK moments of all-time

Looking back at all of the Kardashian-Jenner family’s most iconic Keeping Up with the Kardashians shared with us through KUWTK!

After what will almost be 18 seasons, it’s safe to say that the Kardashian-Jenner family has shared plenty of their tumultuous ups and downs with us, Keeping Up with the Kardashians fans! Let’s take a look at the top 5 craziest moments that have stood out among the rest of the chaos constantly happening throughout their lives.

1. Kim Kardashian loses her diamond earring in the ocean

Starting us off, number one would have to be Kim Kardashian losing her diamond earring.

Her at-the-time partner Kris Humphries was with the family on their vacation to Bora Bora. When playfully throwing Kim into the water, she realized she was missing one of the studs and leading to one of the most memorable Keeping Up with the Kardashians moments ever!

Was it supposed to be funny? No, but did we laugh regardless? Most definitely! As distressed as she was, she did eventually get the earring back, thanks to younger sister Kylie Jenner.

2. Kim Kardashian snaps selfies while Khloe Kardashian gets arrested

Remember when Khloe Kardashian was going to jail for violating her probation after a DUI, and Kim snapped some selfies of the moment?

This scene takes number two, as the youngest Kardashian sister sat in the car as her family drove her to the prison she was meant to stay 30 days in. However, luckily enough she got out in less than three hours due to overcrowding happening at the facility! This was when Kris scolded Kim, saying the infamous line, “Kim would you stop taking pictures of yourself? Your sister’s going to jail!”

3. Kayne West asks Kim Kardashian to marry him

Third on the list is the sweet, wholesome time where rapper and now-husband Kanye West proposed to Kim. This memorable scene that fans could never forget happened on Kim’s 33rd birthday at AT&T Park. Truly a timeless moment that felt like something out of a fairy tale!

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4. Kylie Jenner keeps her pregnancy secret from the public

Taking number four: when youngest sister Kylie Jenner pretty much disappeared from social media hiding the fact that she was expecting Stormi.

The makeup mogul wanted to keep her pregnancy private, which was respectable considering the enormous audience the family constantly has. Kim Kardashian called Kylie’s pregnancy “the best-kept secret of our generation,” accurate as no one was able to officially confirm that the reality star was going to be a mom until she addressed the rumors herself.

5. Tristan Thompson’s cheating scandals

Lastly, Tristan Thompson‘s not one, but two cheating scandals on at-the-time girlfriend Khloe Kardashian. The Canadian basketball player was caught once in April cozying up to a woman who was certainly not Khloe — and this was just days before she was going to give birth to their daughter, True. Just 10 months later, the Cleveland Cavaliers player was caught again, this time with Kylie’s (now ex) best friend, Jordyn Woods. Messy!

Throughout these past 13 years, there have been countless iconic moments that will stand out to all of us! Keeping Up with the Kardashian‘s has had its fair share of chaos when it comes to times in reality television history, so it’s no surprise that we can look forward to even more unpredictable situations in the future seasons to come!