Keeping Up with the Kardashians: The most dramatic, hilarious, and heartbreaking moments of an era

Calabasas, California – Divorces, marriages, heartbreaks, secret pregnancies, and more! For 20 seasons, the Kardashian-Jenner clan has let the world in on all the drama, joy, and epic scandals from their lives on KUWTK.

Keeping Up With The Kardashians first aired in 2007 and is ending after 20 seasons.
Keeping Up With The Kardashians first aired in 2007 and is ending after 20 seasons.  © IMAGO / Everett Collection

While they definitely weren’t the first family to have their own reality show, they were one of the few success stories that proved the world couldn’t wait to "keep up" with the Kardashians.

With nearly 14 years of memories and mishaps candidly captured on film, the Kardashians have managed to create an unbreakable bond with their fan base and side ventures of their own, and it’s all thanks to the show.

A lot has happened over the last 20 seasons of Keeping Up With The Kardashians, and with the series coming to an end, it's time to take a look back at some of the show's most jarring moments.

Kim and Khloe try on true love and battle affairs

Kim Kardashian (r) is currently divorcing Kanye West after six years of marriage while Khloe (l) reunited with Tristan Thompson after their split.
Kim Kardashian (r) is currently divorcing Kanye West after six years of marriage while Khloe (l) reunited with Tristan Thompson after their split.  © collage: screenshot/instagram/realtristan13 & kimkardashian

Khloé and Kim Kardashian had their fair share of romantic mishaps on KUWTK while searching for a fairy tale ending.

Kim’s past love history isn’t exactly a mystery, and her scandalous sex tape with Ray J has long been said to be the reason the Kardashian family was on the map in the first place. The backlash didn’t stop Kim from finding her forever love in someone else.

In season six, the 40-year-old had a whirlwind romance with Kris Humphries that led to a wedding, only for the two to get divorced after 72 days of marriage.

Khloé Kardashian and Tristan Thompson are over... again!
Celebrities Khloé Kardashian and Tristan Thompson are over... again!

It wasn’t long before Kim found her way into the arms of a new man – Kanye West. The two ended up having four kids together, with two through a surrogate.

But in season 20, Kim broke down when addressing marital problems with West, calling herself a “f***ing failure”.

As for Khloé (36), her marriage with Lamar Odom (41) came to an end during season 9 after Odom's raunchy affairs and struggles with drug and sex addiction.

It wasn’t long before he was replaced by NBA player Tristan Thompson (39), who ended up betraying Khloé in a major way. During season 18, it was revealed that Tristan cheated on Khloé with Kylie Jenner’s then-best friend Jordyn Woods, all while Khloé was carrying Tristan’s child.

Tristan has been trying to prove his worthiness to Khloé throughout season 20, there have been recent claims of affairs by several women.

Kris Jenner and Caitlyn’s separation

Kris Jenner (r.) was married to Caitlyn from 1991 to 2013. The latter came out as a transgender woman shortly after.
Kris Jenner (r.) was married to Caitlyn from 1991 to 2013. The latter came out as a transgender woman shortly after.  © collage: screenshot/instagram/caitlynjenne/krisjenner

The matriarch and former patriarch of the Kardashian-Jenner dynasty, Kris and Bruce Jenner – now Caitlyn – provided a united front when the reality show first aired. However, things took a shocking turn between the former couple at the beginning of season nine.

The next season, Kris (65) and Caitlyn (71) decided to separate amicably. In the midst of the following season, the former Olympic athlete came out as a transgender woman and legally changing her name from Bruce to Caitlyn. Soon after her public announcement, she and Kris got divorced.

Caitlyn was not seen on the show after the release of her memoir, The Secrets to My Life, which the Kardashian-Jenner crew felt greatly insulted and misrepresented by.

But she did make an appearance on the show in season 20 via FaceTime when she needed business advice from the all-star momager, Kris.

Though she debated whether to get involved in her affairs, Kris ultimately gave Caitlyn sound advice, something her daughters applauded.

Kourtney’s fearless childbirth experiences

Kourney Kardashian shares three children with Scott Disck. The two had an on-again-off-again relationship throughout the series.
Kourney Kardashian shares three children with Scott Disck. The two had an on-again-off-again relationship throughout the series.  © Screenshot/Instagram/kourtneykardash

There’s no doubt that the Kardashian-Jenner family has grown immensely over the course of the show. Every Kardashian-Jenner had at least one child on the show, except for Kendall Jenner, who plays the role of a "funt", or fun aunt.

But it was Kourtney who really lit up the screen during the finale of season by letting the film crew – and her entire family – in the delivery room for the birth of her second child, Penelope, with then-boyfriend Scott Disick.

When it was time for Kourtney’s final push while giving birth, she iconically reached down to pull out Penelope herself, the same way she did with Mason. But this time, it was filmed and aired for the whole world to see.

In an interview with US Weekly from 2012, Kourtney said, "With Mason, I had no idea I was going to do that. This time, I thought, This is what I'm supposed to do."

Top-secret, baby-making rendezvous

Kylie Jenner shares a daughter, Stormi, with Travis Scott. The pair split in 2019 but seemingly have rekindled their romance.
Kylie Jenner shares a daughter, Stormi, with Travis Scott. The pair split in 2019 but seemingly have rekindled their romance.  © Screenshot/Instagram/kyliejenner

As public as the Kardashians-Jenners were, there were a few secrets they managed to keep under wraps.

During the season 12 premiere, the family learned that Rob Kardashian (34) had been dating Blac Chyna, who oddly enough dated Kylie Jenner’s ex-boyfriend Tyga, too.

Rob continued to shock the family when he announced that he was engaged to the model and the two were also expecting a baby. In 2016, the two welcomed their daughter, Dream, but ultimately split up and have had issues with one another since.

Another well-kept secret was Kylie’s pregnancy and the birth of her daughter, Stormi.

Though the young entrepreneur’s relationship with Travis Scott wasn’t private, the news that the two were going to be parents was not announced until Stormi was born. Though the two split in 2019, it seems like they are on the road to romantic recovery.

Fans of the show will surely miss their weekly televised hangs with the Kardashian-Jenners, but the family has assured viewers they’ll be returning to the screen with a new Hulu show shortly after KUWTK wraps Thursday, June 10 on E!.

Cover photo: IMAGO / Everett Collection

More on the topic Kim Kardashian: