It’s quite impressive that Keeping Up with the Kardashians lasted for 20 whole seasons, airing from 2007 till 2021. All this time gave the family countless opportunities to turn ordinary disagreements into pure TV drama. We got squabbles, fights, marriages, divorces, and even watched babies get delivered, all of which kept the viewers glued to the screens.
Here are some of the craziest, most memorable moments from Keeping Up with the Kardashians.
1. Kim loses her diamond earring (Season 6)
On a family vacation in Bora Bora, Kim realized one of her diamond earrings had fallen into the ocean and immediately burst into tears. With a $75,000 price tag, you can see why. But Kourtney, who was having her own issues at the time, fired off her iconic line: “Kim, there’s people that are dying.” There’s not really much you can do after that, aside from counting your blessings. Funny enough, Kylie later found the earring, so the whole story had a surprisingly happy ending.
2. Kim and Kourtney get into an actual fight (Season 18)
Before season 18 premiered, Kourtney had already wanted more control over how much of her life was being filmed. Kim apparently did not like that approach, and a conversation about who was pulling their weight turned into a physical fight. Thankfully, Khloé stepped in to separate them before some real damage was done.
3. Kim takes selfies on the way to drop Khloé off at jail (Season 3)
After violating her probation following a DUI arrest, Khloé found herself in a difficult situation, prompting Kris and Kim to offer her a ride to jail. Somewhere along the way, Kim decided the lighting in the car was amazing, and so she kept snapping pictures of herself until Kris finally asked her to stop. There’s a time and place for everything, but apparently, reality TV stars live by their own rules.
4. Kim swings her purse at Khloé (Season 2)
A little disagreement at a car dealership grew into something uglier. The argument followed the sisters all the way to Rob’s place, and Kim showed up hoping to smooth things over. She overheard her sisters talking, but when Khloé tried to shut the door on her, Kim snapped. She basically forced her way in and smacked Khloé with her purse.
5. Kris cheers Kim on at her Playboy shoot (Season 1)
When Kim posed for Playboy in 2007, Kris whipped out a digital camera of her own to capture this momentous occasion. She snapped a few behind-the-scenes photos and made sure to praise Kim by saying, “You’re doing amazing, sweetie.” It’s not so much about what she said but how she said it. At that moment, Kris sounds like a proud mom taking pictures at a school recital.
6. Kourtney helps deliver her own baby on camera (Season 4)
In the Season 4 finale, the viewers were given a sneak peek into the delivery room as Kourtney gave birth to Mason, her first child with Scott Disick. Several family members were there, and the cameras caught the moment Kourtney reached down and helped pull the baby out herself. Now that’s pretty metal.
7. Kanye rents a baseball stadium to propose to Kim (Season 9)
Kim’s 33rd birthday present was a bit more than she was hoping for, but in a good way. Kanye brought her to AT&T Park in San Francisco, where he had rented the stadium and hired an orchestra. Then he got down on one knee with a 15-carat diamond ring and proposed to Kim while friends and family were watching from afar. You just can’t beat a birthday present like that one.
8. Kris gets fake-tackled by Kim’s security (Season 19)
In the show’s penultimate season, Kris was tired of having to show ID at her daughter’s house. Then one day, Khloé called Kim in a panic, saying security tackled their mom. Kim hurried home to find Kris lying on a stretcher wearing a neck brace, only to discover that the entire scene had been staged as a prank. While the surprise certainly caught Kim off guard, it also raised questions about how much preparation went into the elaborate setup and whether the reaction justified the effort.
9. Kim divorces Kris Humphries and starts wearing wigs (Season 7)
Kim divorced Kris Humphries just 72 days after their wedding. She later stated that she had married for love and felt overwhelmed by the rapid pace of events. On the show, Khloé suggested that she do something silly to distract herself, and she complied. That’s when Kim started wearing wigs like she was dodging the CIA. At least this little stunt didn’t have any long-lasting effects on Kim and was easily reversible.
10. The family dresses up as each other (Season 17)
At the end of their Wyoming family trip, everyone showed up to dinner dressed as one another. Khloé did a spot-on Kris, and Kourtney played Kim. Kendall went all in on her Kylie impression, complete with a pink wig, and kept smearing red lipstick all over her mouth and teeth. It was all done for fun, so thankfully, nobody got pressed (too much).