The Top 10 Moments Ever From ‘Keeping Up With the Kardashians’

Keeping Up with the Kardashians - Season 11
Brian Bowen Smith/E! Entertainment

As if specifically scheduled to give us a mindless escape from the rigors of our late-stage pandemic life, Keeping Up With the Kardashians returned for its 20th and final season Thursday, March 18. Set against gorgeous blue skies, cavernous rooms, and lots of white furniture, the episode tackled Kim‘s bar exam (go Kim!), Kourtney‘s hormone shots, Scott Disick’s inability to move on, and more.

It’s hard to believe that the E! reality show has been on since 2007. Kim has gone through two weddings and divorces, Kylie Jenner has gone from 10-year-old to near-billionaire, and Rob Kardashian has gone from Hollywood heir to recluse to reemerging reality star.

We look back at some of Keeping Up With the Kardashians’ most outrageous moments — even by Kardashian standards. From Kris Jenner’s motherly meddling to Khloé’s brief jail stint to a Kourtney-Kim showdown, these are the moments we’ll never forget.

Kris Praises Kim’s ‘Amazing’ Playboy Shoot

Keeping Up With The Kardashians Sweetie GIF by PeacockTV - Find & Share on GIPHY

In the quote that launched a thousand memes, Kris gave Kim a pep talk during her daughter’s Playboy photo shoot in Season 1, saying, “Kim, you’re doing amazing, sweetie,” while snapping her own photos with a digital camera. (Ever the supportive mother!)

Kim Commemorates Khloé’s DUI arrest

Back in the days before front-facing cameras on cell phone, Kim snapped selfies with a digital camera as Khloé reported for a 30-day jail sentence for a probation violation. “Kim, will you stop taking pictures of yourself? Your sister’s going to jail,” an exasperated Kris said.

Kris’ Upper Lip Swells to the Size of Calabasas

On what must have been the tropical vacation from hell, Kris suffered an allergic reaction to something she ate in the Dominican Republic — making her upper lip look like “a Who from Whoville,” in her words — and she broke her toe. At least she had an in-room massage to help ease her suffering.

Rob’s Viagra Fiasco

In one episode, Rob experienced a certain problem he hadn’t experienced since middle school after drinking Viagra-spiked coffee Kris had prepared for her then-spouse, who later came out as Caitlyn Jenner. Kris met Rob at the doctor’s office and fessed up to spiking the coffee with “a little, kind of like, a male enhancement little drug…thing.”

Kourtney Keeps Things in Perspective

Kourtney had little sympathy when a sobbing Kim realized she lost her earring after getting dunked in the ocean in Bora Bora. “Kim, there’s people that are dying,” Kourtney said, observing her sister’s histrionics. (Fans cited that immortal quote in 2020 when Kim hosted a birthday bash on a private island during a global pandemic.)

Kris Mocks Kim’s 72-Day Marriage

When Kim and Khloé told Kris she shouldn’t be purchasing a house for Rob, Kris told them all to “f—k off and go think of something else to talk about.” She also made a snarky comment about Kim’s short-lived marriage to Kris Humphries, saying, “’I’m married for 72 days.’ Really? That was normal.”

Kim’s Breast Milk Treatment

Making the very wise choice to get medical advice from the Internet, Kim read online that breast milk would help alleviate her psoriasis. Cut to the then-nursing Kourtney giving her sister a dose of breast milk “fresh off the boob.”

Kris Goes Casket-Shopping

Looking for a “fab resting place,” the family toured cemeteries and mausoleums in the Los Angeles area to figure out where they wanted to spend eternity. Kris got really into it, clambering into a casket to try it on for size and even lying down on top of someone’s sarcophagus. “She’s, like, disrespecting the dead people in there,” Kim complained (before getting distracted by a duck).

Kim Wins a Range Rover in a Poker Game

Sitting down with Kim and Khloé for a game of poker, Kris must have thought herself a card sharp, what with her indoor sunglasses and all. Perhaps banking on that bravado, Kris bet her Range Rover on a bluff. The professional dealer at the table laughed, but Kris wasn’t laughing. Kim won the hand, and walked away with a new set of wheels.

Kim and Kourtney Get Into Fisticuffs

Kourtney’s salty attitude about filming KUWTK has long been a thorn in Kim’s side, but the two sisters came to blows in Season 18 during an argument about work commitments. Kourtney got in Kim’s face, threats were exchanged, and then hands and fists went flying.

Keeping Up With the Kardashians, 20th and Final Season Premiere, Thursday, March 18, 8/7c, E!