Kourtney Kardashian's Transformation Has Left Everyone Stunned

Keeping Up With the Kardashians has surpassed all of expectations, spanning 20 seasons and 14 years. The E! reality series gave fans a look inside the family of then-socialite and bestie of Paris Hilton, Kim Kardashian. From relationship woes, to clothing lines, to sister arguments and even the birth of 10 grandchildren, KUWTK followed the lives of Kim, Kourtney, Khloé, Kylie, Kendall, Kris, and Rob, plus Scott Disick and Caitlyn Jenner as they managed fame and family.

Despite consistent jokes that none of them would have jobs if it weren't for sister Kim, it is the personalities of the SKIMS owner's family that kept fans coming back. The one sister that remains a fave for millions of viewers is the OG to reality TV, Kourtney Kardashian. Kim may have dubbed her the "least exciting to look at," but fans beg to differ. The celebrity has gone from simply the eldest of the Kardashian bunch to her own household name as a business owner, mother of three, and beloved reality star.

"I never thought it was going to become this thing," said Kourtney speaking to Paper magazine about the success of KUWTK. "From when we shot the sizzle reel or whatever. It got greenlit straight away." The show has undeniably become "this thing" and the journey of Kourtney from rich daughter of a famous lawyer to millionaire businesswoman was partly to thank. Let's dive into the transformation of the Kardashian that left everyone stunned.

Anyone who has heard of the Kardashians (a.k.a. anyone who hasn't been living under a rock the last 20 years) will immediately point to Kim Kardashian as the helm of the family's TV legacy. However, it was older sister Kourtney Kardashian who first tested the reality TV waters.

Two years before the premiere of Keeping Up With the Kardashians, Kourtney joined the cast of Filthy Rich: Cattle Drive, an E! network series, of course. The 2005 series followed the "sons and daughters of 10 celebrities" as they left "their everyday luxuries behind to drive a herd of cattle across the beautiful treacherous terrain of Colorado" (via NBC), and Kourtney was one of them.

According to TooFab, the reality star was cast as Robert Kardashian's daughter, and starred in the one-season series before famously dating Scott Disick. "I do not spend any time outdoors, I just despise the outdoors," said the young Kardashian in a throwback clip of the reality series. "I can't imagine why I'm leaving my nice house to sleep in a tent for three weeks and ride on horses."

The wealthy celebrity kid (at the time) was true to character, making sure her outfit was on point regardless of her whereabouts. "I don't know, I just think you have to look cute when riding, or no matter what you're doing, even when we're hanging out by the campfire," said Kourtney. "A cute outfit is key."

Just one year after testing out her chops on an E! reality series, Kourtney Kardashian met Scott Disick, who would become her most well-known relationship. Four years her junior, Scott and Kourtney found love in 2006 at a Mexico party thrown by the couple's friend Girls Gone Wild creator Joe Francis, according to Us Weekly. The two hit it off, beginning a nine-year relationship. In 2007, Kourtney's family joined the E! network, bringing Scott along for the ride.

Kourtney and Scott's relationship has been a main topic of conversation on Keeping Up With the Kardashians since the beginning. From Kourt suspecting Scott of cheating in Season 2, to a Miami hookup leading to their first child Mason Dash Disick, the on-again, off-again relationship has kept viewers engaged.

In 2011, when Scott attempted to buy an engagement ring for his then-girlfriend of five years, her response was, "Why mess it up?" Then in 2012 and 2014, the couple welcomed their second and third children, Penelope and Reign Disick, respectively. Despite fans rooting for the couple to stay together, Scott and Kourtney officially called it quits in 2015 after photos surfaced of Lord Disick cheating with ex Chloe Bartoli.

Kourtney's relationship status didn't stay single for long. The reality star was tied to model Younes Bendjima in 2016, but the relationship lasted just two years (via Us Weekly). Then in 2021, the Kardashian social media confirmed her relationship with old-time friend, Travis Barker.

In the first few seasons of Keeping Up With The Kardashians, Kourtney Kardashian was the party girl of the Kardashian crew. The young celeb frequently went out with younger sister Khloé Kardashian, even sharing a kiss with Orange Is the New Black star Jackie Cruz on a drunken Miami night. However, after giving birth (on camera, of course) to three kids, Kourtney quickly shifted gears from Hollywood party girl to eco and health-conscious mom.

In an interview with Rose Inc., the celeb revealed the only thing keeping her in bed these days are "weekend cuddles with [her] babies and movie nights." The reality star also admitted the only thing she will never apologize for is "kissing [her] kids on the lips."

Kourtney's kids Mason, Penelope, and Reign changed the star's outlook on life and fame, despite the three little ones regularly making appearances on Keeping Up With the Kardashians. "No matter what it is that I am doing, someone has something to say, good or bad," said Kourtney. "The worst, though, is when people I don't know give unsolicited parenting advice. No one knows my kids better than me, I've got this, I'm good, thanks." 

The star revealed in an episode of KUWTK that she hasn't ruled out more kids in her future, opting to freeze her eggs. But, Kourtney's journey into motherhood has prompted her to adjust one major part of her life: filming the show.

It was in 2018 that Kourtney Kardashian noticeably had a change of heart when it came to filming her family's show Keeping Up With the Kardashians. In one of the biggest sister fights with Kim, Kourtney, and Khloé Kardashian, the eldest of the trio was arguing with her younger sisters about making time to shoot a family Christmas card. The fight quickly escalated to Kim calling out Kourtney for never wanting to work. "If I had enough money, I wouldn't work — I wouldn't do the show," admitted Kourtney, according to BuzzFeed. "I would be a full-time mom. That's what I want to do."

Past interviews with Kourtney revealed the celeb hasn't always been 100% into the idea of filming the family reality series. In 2011, family matriarch Kris Jenner released a memoir that revealed, "Kim and Khloe jumped up from their chairs, they were so happy" to do the show, yet "Kourtney was a little quiet because she was somewhat hesitant." Then in 2014 (a little over halfway through the 20 seasons of KUWTK), Kourtney revealed that "sometimes [she wishes they] weren't filming." The celeb continued, "I love being a [mom] and sometimes I just wish no-one knew who I was" (via Digital Spy).

The eldest Kardashian seemingly got her wish, telling Entertainment Tonight she decided to step back from filming the show just a bit, deciding to focus on motherhood and her new business venture, Poosh.

What is Poosh you may ask? After watching her sisters find their niche in creating their own businesses like SKIMS, Good American, Kylie Cosmetics, and an 818 Tequila Brand, Kourtney Kardashian seemingly ventured into finding out "what it takes to run a f**king business" (ahem, Kim Kardashian).

"I'm happy that I didn't let them push me into what was the right timing for them," Kourtney said to Paper magazine in May 2019. "Maybe a couple years back, I almost started a couple different things because I felt like everyone was pushing me." The reality star instead decided on creating her own online lifestyle guide called Poosh, named after her daughter Penelope.

In the interview with Paper, Kourtney revealed the concept came up after a chat with her best friend made her realize "there was a space missing that didn't feel welcoming, and non-judgmental." The Keeping Up With the Kardashians star continued, "I feel like I'm constantly asked, 'How do you do this? What's that salad you guys are eating on your show?' It's nice to share it with people and have that space to do so."

The Kardashian further shared her excitement to Rose Inc., revealing she is "most surprised by how fulfilling" she finds her new job. The celeb previously told Paper, "I feel like this is my thing, and I'm happy."