These 22 Throwback Kylie & Kendall Jenner Moments From 'KUWTK' Show How They've Evolved

by Savannah Walsh
Frederick M. Brown/Getty Images Entertainment/Getty Images

When doing a rewind on the E! reality series, Keeping Up With the Kardashians, there are several hilarious throwback storylines. From Kim's iconic moment losing her diamond earring in the ocean to some of Scott Disick's best pranks, there's a reason the antics of this family has kept the world's attention for 16 seasons. But viewers haven't seen any of the Kardashian-Jenners quite literally grow up as fully as they have Kylie and Kendall. Some of Kylie and Kendall's best throwback KUWTK moments give insight into how they've evolved over the years.

Whether they're playing jokes on their older siblings or getting some life advice from their parents, older Kylie and Kendall moments reveal the most relatable, hilarious, and sometimes outlandish KUWTK episodes. Who hasn't felt a little embarrassed by a parent or annoyed by persistent paparazzi? (Ok, maybe that's just a Kylie and Kendall thing.)

There's a lot to dissect in the early days when one considers the major mark both sisters have made on pop culture. From Kendall's super successful modeling career to Kylie's foray into cosmetics and becoming the youngest self-made billionaire, according to Forbes, the youngest Kardashian-Jenners were destined for the spotlight. Let's relive some of the best moments from their first few seasons on the show, when fame was just a twinkle in their eyes.


When Kendall & Kylie Pretended To Be Kim

Before Kendall & Kylie were superstars in their own right, the duo loved making fun of older sister Kim. In this throwback, the sisters pretend to be Kim and Kris and the impression is not far off, tbh.


When Brody "Babysat" Kylie & Kendall

One of the most iconic younger Kylie & Kendall moments came courtesy of Brody Jenner's lackluster babysitting skills. When Brody is supposed to be keeping an eye on his sisters, they can be found in the next room mastering a routine on a stripper pole. Interestingly enough, Brody isn't asked to watch the kids again.


When Kylie & Kendall Exposed Kim's Injury Lie

Kylie and Kendall lived for a prank or dramatic exit. In this moment, the sisters find out that Kim faked an injury to get out of taking them to the beach. Kendall's flower toss is everything.


When Kylie Stood Up To Caitlyn

One of the most overly dramatic moments involving Kylie came when Caitlyn caught her innocently ordering a pizza. The only problem is a boy was also in her room, causing Kylie to speak out about how unfair it is that she can't have male friends. Also, the pan in to the young boy in the clip is unintentionally hilarious.


When Kylie Dyed Her Hair Blue

Moral of the story: don't dye your hair blue. Smurf comparisons will be made.


When Kendall Schemed For a Tattoo

When Kendall wanted her first tattoo, nothing as insignificant as parent approval was going to stop her from taking a trip to Vegas for one. In the words of Kylie, "It is crazy that my sister is asking me to go to Vegas with her, but I'm in." Us, too.


When Kendall Began Pursuing Her Dreams

Kendall's mega-successful modeling career began with this clip. When Caitlyn voices his concerns, Kris jokingly says that it's not like she's booking Kendall a Victoria's Secret commercial. If only they could predict her Angel runway status years later...


When the Family Tried To Keep Kendall From Moving Out

When Kendall debated moving out ahead of her 18th birthday, she was met with some resistance from the rest of the fam. And there's some weirdly hedged-in Six Flags discussions for good measure, too.


Kylie & Kendall's Prank on Rob

Again, Kylie & Kendall are always down for a prank and this one involving stealing Rob's beers got a little complicated when their dad got involved.


When Kris Wanted to Join Kylie & Kendall's Squad

Kris attempting to join Kylie & Kendall's friend group by talking about Justin Bieber is definitely awkward, but the girls saying she's having a midlife crisis or going through menopause...is admittedly kind of harsh.


When Kendall's Dog Responsibilities Are Questioned

When Kendall finally gets a dog of her own, things get a little...messy when it comes to training.


When Kendall Awkwardly Gets the "Talk" From Her Older Sisters

Having a talk with your mom or older sister about getting your period is almost always a little awkward. Having that conversation on reality television? Super uncomfortable.


When Kylie & Kendall Helped the Whole Family Break Kris' Smoking Habits

When Kourtney, Kendall, and Kylie want to get Kris to stop smoking, they decide to get creative with their hydration tactics.


When There Was Drama Over Kendall's Sweet 16

When Kris casually starts planning Kendall's sweet 16 IN THE BAHAMAS, despite her wishes, stuff starts to go down between the momager and her adolescent daughter.


When Kylie Was Growing Up Too Fast

When Khloe showed Kylie some makeup tips, Caitlyn started to fear that his youngest daughter was growing up too fast. But as it turns out, Kylie and makeup has made for a pretty lucrative combination.


This Reaction

We live for sisterly check-ins such as these.


When Kylie & Kendall Went Missing In Thailand

When Kendall and Kylie go missing in Thailand, the family is divided over whether it's a prank or cause for concern.


When Kylie First Dealt With Paparazzi

Now paparazzi is a regular fixture in Kylie's life, but in this throwback clip, Caitlyn and Kylie talk about the issue for one of the first times.


Honestly, Anytime the Sisters Would "Play Fight"

Kylie and Kendall's fights were, as bad as it is to admit, always a little funny and relatable. What siblings haven't had a knockdown drag out before?


Iconic Fashion Such As This

You do you, Kylie.


Throwbacks Within Throwbacks

Home videos of Baby Kendall are the cutest thing ever and we can't be convinced otherwise.


The Cuteness Is Worth Another Look

I mean...

Kylie and Kendall may now be moguls in their own right, but it's always fun to look back on some of their most hilarious, outrageous, and relatable moments. KUWTK wouldn't be the same without some of their best early antics.