Chances are, if we were to ask anyone about the Kardashian-Jenner family, most people would be able to say something they've heard about the family. They're considered the royalty of reality TV. While they were born into privilege, it was their family dynamic (and matriarch Kris Jenner's business sense) that turned this family into one of the world's most famous on Keeping Up With the Kardashians. Several members of the family are billionaires. They have their hands in so many money-making projects, and of course, there's drama between it all.
When it comes to the Kardashian and Jenner family, there are a lot of players. For anyone unfamiliar, here's a short rundown of the players from KUWTK. Kris Jenner was married to Caitlyn Jenner for 23 years before she transitioned. During their marriage, they raised Kourtney, Kim, Khloé, Rob (Kris' kids with the late Robert Kardashian) and the two girls they shared, Kendall and Kylie. Added to the family are their significant others. Plus, most of them (well, everyone except Kendall) have kids of their own now.
There's been a lot of drama and conversations surrounding these famous reality TV stars. Given that, the most popular and talked-about moments in this family all seem to center on drama and controversy more times than not.
Here are the top 20 moments from the Kardashian and Jenner family, in no particular order.
Kim's Personal Video
One of the first big talked about moments for the family was when in 2003 when a personal tape featuring a young 23-year-old Kim Kardashian with her then-boyfriend Ray Jay doing adult things surfaced and was sold. She later said it was one of her biggest regrets, that she was on drugs, but some say it was a business move — because look where it got them.
Khloé Went to Jail
Before making headlines for being a mom and her relationship troubles, a major talked-about moment for Khloé Kardashian was when she was arrested for a DUI documented in the first season of the show. She was given probation, which she violated, and was sent to jail. Although she only had to spend a few hours there, due to "overcrowding," she technically was in jail. She's come a really long way since her younger years.
Kylie's Chicken Moment
The Kardashian-Jenner family wasn't always mega popular. Still, their reality TV show is what catapulted them to the stardom they're enjoying now. With the show, fans could see candid moments (whether they were authentic or not is another story). One of the funniest moments discussed for a long time was Kylie mistaking a pig for a chicken in a deleted scene for KUWTK.
Kim & Kanye vs. Taylor Swift
A strange chain of events led to an unexpected beef between Kim and Kanye West and Taylor Swift. It all started in 2009 when Kanye interrupted Taylor at the MTV Music Video Awards. In 2015 it all seemed to finally be behind them until a song with lyrics came out from Kanye, who said he reached out to her before the release for her approval, claiming she did. It turned into a he-said-she-said, with Kim releasing receipts. It was … a moment.
An Accidental Photo Leak
Khloé has been open about feeling pressure from the media. Still, all that became huge news after an unauthorized image of Khloé hit the internet. Apparently, the unedited photo was accidentally posted, which prompted their legal team to scrub the image from the internet. The photo was lovely, just not super edited like Khloé usually shares. Khloé addressed the headlines on Instagram asking people to be kinder.
Lamar Odom Enters & Exits the Scene
Khloé has had several moments in the spotlight that were widely talked about. Her marriage to NBA star Lamar Odom was one of them. The pair met, got engaged, and then married all within a month of meeting in 2009. They seemed happy and starred in several spin-off shows for E!. But it all came to a head when Lamar was battling addictions, and nearly died while cheating on Khloé. The two finalized their divorce in 2016.
Kendall's Pepsi Ad
For the most part, Kendall Jenner is the least likely to be at the center of the drama. But when she is, it's usually a doozy. In 2017, a Pepsi ad starring Kendall Jenner was heavily criticized for appropriating a nationwide protest in response to the police shooting of Black people. It was taken down pretty quickly, but fans never forgot the insensitivity.
Caitlyn Jenner Announced She Was Transitioning
After 23 years of marriage, raising their kids together, Kris and now Caitlyn announced their divorce. In 2015, sharing with 20/20, telling Diane Sawyer she was a woman. In July 2015, she reintroduced herself to the world as Caitlyn on Vanity Fair's cover.
Kim & Kanye File for Divorce
These two seemed like the perfect match for each other. Kim and Kanye were both driven, successful, OK with the level of fame each had. And they are parents to four adorable kids. But a lot was going on between them as well. After months of speculation, mental health issues, erratic behavior, and distance seemed to hit the fan and Kim and Kanye filed for divorce in February 2021.
Tristan Thompson Caught Cheating
After all the drama Khloé had with her first marriage to Lamar, fans rooted for her to find someone special. She deserved to be happy, and she was finally pregnant, and everything seemed to line up perfectly with her new boyfriend, NBA player Tristan Thompson. Then the public found out her new beau, and the dad to her soon-to-be baby, was caught cheating on her just days before she was set to give birth. She took him back. It happened again, this time with Kylie's BFF, Jordyn Woods. Tristan and Khloé grew close again while the global health crisis was going on, quarantining with their daughter, True.
Kourtney the 'Least Exciting'
We've seen some drama between the Kardashian and Jenner sisters throughout their TV show. But everything seemed to escalate in 2018 between Kim and Kourtney. The two are different people, but Kim threw some cruel remarks at her sister, saying she was "the least exciting" of the sisters to look at. And, honestly, that was just the start of it all.
Surprise! Kylie Had a Baby
There was a lot of speculation that Kylie was pregnant in 2017, but given that she was always in the spotlight, there was no way she could hide that forever, right? Well, as it turned out, she had a lot of people she could trust in her life because there was not one single photo of her pregnant anywhere. She surprised the world in February 2018 when she confirmed the news herself… she was a mama.
Rob & Blac Chyna's Custody Drama
Rob Kardashian is the quiet sibling after stepping away from the spotlight close to a decade ago. But in late 2016, he welcomed his daughter Dream with his on-again, off-again girlfriend during that time, Blac Chyna. The two had a tumultuous relationship in the spotlight. They had custody drama with their daughter, which was still going on in 2020.
Kim Was Robbed in Paris
On October 3, 2016, Kim Kardashian was in Paris, France, for fashion week when the unthinkable happened. Alone in the hotel room, Kim was robbed, tied, and forced into the bathtub after men entered her room to rob her. "I think they robbed me of 5 million dollars," Kim told authorities. "Then they left on the run."
Kylie's a Billionaire
In March 2019, Forbes had Kylie as the cover person for its billionaire edition. At 21 years old, she was named the world's youngest "self-made" billionaire. The title was debated on social media, with some claiming she's not really self-made, given her access to money. A year later, Forbes said it had made a mistake, and Kylie was really only worth around $900 million (yes only).
Caitlyn Writes a Book & Causes a Rift
In mid-2017, Caitlyn published a book titled The Secrets of My Life, where she detailed her life from childhood through transition. In the book, she didn't hold anything back. The Kardashian sisters felt Caitlyn had overshared several things about their mom, Kris Jenner. It led to a rift between them, and Khloé's relationship with Caitlyn was especially strained.
Kanye for President?
There have been a lot of moments in Kanye's life where he's made the headlines for things he's said. But, when he announced he was throwing his hat into the presidential ring, running for president in 2020, well, everyone was talking about it. Add in some extremely personal things he said during the campaign, and it was a long-spoken about moment.
Kim Takes on Prison Reform
Kim, arguably the most famous of the Kardashian-Jenner women, was famous for being famous. People didn't take her seriously when she launched several (successful) businesses. So when she launched her law career and said she was going into prison reform, it was all anyone was talking about for a while.
Kourtney & Scott Break Up for Good
Kourtney and Scott Disick had been together for a long time. They have three children together, and while they never did officially tie the knot, they'd been a couple since the beginning of the reality show. But after years of conflict, a substance issue with Scott, the two broke up — for good — in 2015.
'KUWTK' Is Going Off-Air
In September 2020, Kris announced the family's iconic show, Keeping Up With the Kardashians, was coming to an end. The show has been on the air for 14 years and 20 seasons. The reality stars will close the doors in 2021 — the end of an era.
