‘KUWTK’s 10 Most Dramatic Moments Ever: From Kimye’s Wedding To Caitlyn’s Transgender Reveal

Take a look back at the most dramatic moments from 'KUWTK' as the series comes to an end.

Image Credit: AP Images

Keeping Up with the Kardashians is coming to an end. The show is officially concluding after its 20th season airs in 2021, but at least there’s already countless memorable scenes stored in the show’s archives. There are many, given that the show premiered in 2007, but HollywoodLife has picked out 10 moments that especially rattled and moved fans.

A throwback photo of the cast of Keeping Up with the Kardashians, from left to right: Scott Disick, Rob Kardashian, Kim Kardashian, Kourtney Kardashian, Khloe Kardashian, Kylie Jenner, Kris Jenner and Kendall Jenner. (AP Images)

Of course, such scenes wouldn’t be as iconic without the family members that made it happen: Kris Jenner, Caitlyn Jenner, Kim Kardashian, Khloe Kardashian, Kourtney Kardashian, Rob Kardashian, Kendall Jenner, Kylie Jenner, Kanye West and Scott Disick. Now, let’s begin that trip down memory lane somewhere in Calabasas ahead of the new season premiere:

Kanye’s Proposal To Kim

Kim was treated to the surprise of her life when Kanye proposed in the middle of San Francisco’s AT&T Park — and it was her 33rd birthday, on top of that! It was a magical moment complete with a majestic fireworks display and an orchestra playing Lana Del Ray’s song “Young And Beautiful,” which Kim’s friends and family all got to witness from the sidelines. The proposal happened in Oct. 2013, and was featured mid-way into Season 9.

Kim’s family and friends didn’t even see this proposal coming — except for Kris, of course, who arranged the surprise. On the jet ride over to San Francisco, Khloe and Kourtney debated what Kris and Kanye could possibly be up to.

Caitlyn Jenner’s Transgender Reveal

Caitlyn (then known as Bruce) came out as a transgender woman to Diane Sawyer on 20/20 in April of 2015. However, the KarJenners’ reactions to this big news wasn’t revealed until a two-part special called “About Bruce” aired in Season 10 of KUWTK in May of 2015. It was one of the most emotional episodes on the family’s longtime show, and while Kendall said she “couldn’t ask for a better dad,” she tearfully admitted, “I think it’s just scary when someone says that Bruce is going to be gone.”

To that, Caitlyn assured her daughter, “I never said Bruce is going to be gone…I’m not going anywhere.” Her stepdaughters Khloe, Kim and Kourtney also gave confessions during the heavy episode, and at the time, all were unsure if their stepdad would be transitioning into a woman.

Kourtney Giving Birth On Camera

Kourtney Kardashian, Penelope Disick
Kourtney Kardashian gave birth to her daughter, Penelope, in front of cameras in 2012. (New Media Images/SplashNews)

Amid the many scandals and family dramas to happen on KUWTK, this may have been the most shocking scene: Kourtney giving birth to her second child with Scott, their daughter Penelope, right in front of the cameras in July of 2012! The show even aired the moment Kourtney literally reached down and pulled out the newborn baby from herself. The completely uncensored scene, although raw and beautiful, left fans with mixed feelings.

The Kimye Wedding

Kim and Kanye followed up their grand proposal in San Francisco with an even grander wedding ceremony at the Forte di Belvedere, a 16th-century fortification in Florence, Italy! Kim exchanged vows with Kanye in a Givenchy Haute Couture gown, which made for a breathtaking scene on episode 13 of Season 9.

It wouldn’t be a KUWTK episode without drama, though — even if this was supposed to be the happiest day of Kim and Kanye’s life! Rob opted out of his sister’s wedding last minute after reading negative comments about himself online, and Kim wasn’t exactly happy with Kylie’s blue hair.

Khloe Learns Tristan Cheated

Khloe’s relationship with her boyfriend at the time, Tristan Thompson, forever changed when footage of the Cleveland Cavaliers player making out with one woman and motorboating another was released in Oct. 2017. The tape dropped just three days before Khloe was due to give birth to her and Tristan’s daughter, True Thompson, in April of 2018.

From Scott to Kylie, KUWTK revealed each family member’s reaction to the blindsiding footage. Fans even saw Khloe’s initial reaction to the tape, after Kylie mustered up the courage to break the bad news to her sister. Afterwards, Khloe called Kim and in a grave tone and asked, “What the f–k is that?”

Caitlyn & Kris Split

Kris and Caitlyn (then called Bruce) revealed that they’re better off as friends than lovers in the Season 9 premiere of KUWTK. While they had no intentions of formalizing this split with a divorce (yet), it was clear that this 22-year marriage was over during a family meeting with Kim, Kourtney, Khloe, Rob, Kendall, Kylie and Scott.

Caitlyn revealed that she’s keeping her beach house in Malibu, where she had been living separately from Kris. Kylie and Kendall’s dad added that she is “very happy” with their “current arrangement.” However, Caitlyn clarified that “nobody is getting divorced” — leaving everyone else confused, except for Kris. The family matriarch was just as happy about their unique living arrangement, telling her children, “We’re better as friends than we are the other way.” However, Kris and Caitlyn did eventually finalize their divorce in Dec. 2014.

Kim’s Divorce From Kris Humphries

Okay, so this scene technically happened on a KUWTK spin-off, Kourtney & Kim Take New York, in 2012. But it’s one of those scenes that has been used in countless GIFs: Kim revealing to Kourtney that her “feelings changed” for basketball star Kris Humphries, whom she had just married. They soon split after just 72 days of marriage.

“I feel sad. I feel bad for the guy. I changed his whole life and he fell in love with me and I fell in love with him and now my feelings have changed. You don’t think I feel bad that I invited all these people to this huge wedding and flew everyone out, I wasted everyone’s time. I wasted everyone’s money, I wasted everyone’s everything…at 30 years old I thought I’d be married with kids and I failed at that,” Kim told Kourtney through tears.

Kim & Kourtney Get Into A Physical Fight

Kim and Kourtney had a full-out brawl in Season 18 of KUWTK! Kim slapped her sister while Kourtney left the KKW Beauty owner with scratch marks after yet another fight about Kourtney’s “work ethic,” since the Poosh blogger wanted to distance herself from the family show. Khloe tried to intervene, while Kendall watched on helplessly.

Kim Says Kourtney Is The ‘Least Exciting’ To Look At

While clashing over when to take the family Christmas card photo in Season 15, Kim lashed out at Kourtney with a few iconic one-liners. “Maybe if you had a f–king business you were passionate about, then you would know what it takes to run a f–king business,” Kim snapped. When Kourtney exited the dramatic conversation, Kim quipped that her sister is “out” of the photo shoot because she’s “the least exciting to look at.” Ouch.

Kim Loses Her Diamond Earring

We had to save the best for last! In what has since become one of the most meme-able scenes in KUWTK history, Kim had an emotional breakdown after losing her $75,000 diamond stud earring in the ocean during a family vacation in Bora Bora in 2011. The earring came off after her husband at the time, Kris Humphries, casually tossed Kim into the ocean. Kim’s tears didn’t move Kourtney, who memorably told her sister, “Kim, there’s people that are dying.”

Thankfully, Kylie saved the day by diving in and finding the earring on the ocean floor!

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