Keeping Up With The Kardashian's Biggest Changes Since The First Season

It's been 14 years that the Kardashian-Jenner family has taken over the E! network with their highly rated series Keeping Up with the Kardashians. The show gave the world insight into the lives of Kim Kardashian, Kourtney Kardashian, Khloé Kardashian, Kendall Jenner, Kylie Jenner, Rob Kardashian, Kris Jenner, Caitlyn Jenner, and Scott Disick, plus all of their family and friends. 

The success of the show came as a shock to even the Kardashians, who revealed to Andy Cohen in an episode of For Real: The Story of Reality TV that they were originally a fill-in for Lindsay Lohan's family. "The Lohans were supposed to do a show then it got canned or something happened where it just didn't go into production," said Khloé (via The Sun). Sister Kim added, "They needed to fill the slot ASAP," to which Cohen shockingly asked, "You were Lohan replacements?" The Kardashians admitted they were, adding, "They told us, 'Don't get too comfortable. You're just filler. You'll just last one season.'"

Well, who's laughing now? The show has lasted 20 seasons and turned the Kardashian family into pop-culture icons. From owning small boutiques in Calabasas, Calif. to building million-dollar brands, the transformation of each Kardashian as they grew in fame will leave those unfamiliar with the show shocked.

The Kardashian sisters took fans through their relationship ups and downs

Across 20 seasons of Keeping Up With the Kardashians, perhaps the biggest changes came from the various romantic relationships the family members shared with fans. Combined, the Kardashians went through three marriages, four divorces, and countless relationship ups and downs.

Kim Kardashian – who already married and divorced her first husband before the reality series premiered — took fans through boyfriends Reggie Bush, Miles Austin, and even bodyguard Shengo Deane. The Skims owner filmed the planning of her elaborate wedding to NBA player Kris Humphries, and even let cameras in on her 72-day marriage and then lingering divorce in Kourtney and Kim Take New York. Kim's relationship with Kanye West was a bit more hush-hush, but the reality star didn't shy away from sharing some of the details of the couple's Italian wedding and plight to get pregnant and expand their family. The final KUWTK season is expected to touch on the Wests' impending divorce.

Kim wasn't the only sister to go through marriage and divorce on the show. Khloé Kardashian fell in love with NBA player Lamar Odom on camera, planning (and filming) a wedding in just nine days (via Us Weekly). The couple even landed their own spinoff Khloe and Lamar, before Lamar's behind-the-scenes struggles with addiction became too personal for the cameras. Khloé's divorce in 2016 was, of course, a storyline.

Perhaps the most-talked-about relationship to be followed through the show, however, comes from eldest sister Kourtney Kardashian.

Kourtney Kardashian and Scott Disick were a hot topic on the very first episode

OG fans of Keeping Up with the Kardashians remember the first episode of the series, which premiered in 2007. The show followed socialite Kim Kardashian as she introduced the world to her family while planning her mother Kris Jenner's 16th wedding anniversary party (via IMDb). The sideline story in episode one was Kris' skepticism of her daughter Kourtney Kardashian's new boyfriend — none other than Scott Disick.

The young couple was all over each other in the early seasons of KUWTK, having just met a year prior at a 2006 party in Mexico, according to Us Weekly. Scott would soon become Kourtney's longest relationship, lasting almost a decade (a lifetime on television). Throughout the 20 seasons of KUWTK, Kourtney and Scott's relationship would have such dramatic ups and downs, that fans even today hope the two might get back together.

In Season 2, Kourtney breaks up with Scott (the first time) due to accusations the Lord Disick was cheating. His behavior didn't sit well with the Kardashian family, who wasn't thrilled to learn a Miami hookup between the on-again, off-again couple would lead to Kourtney's first pregnancy. After expanding their family with two more little ones, Kourtney and Scott finally called it quits in 2015 after photos of the reality star cheating on Kourtney surfaced on the internet.

Kris Jenner now has 10 grandkids

Despite the relationship ups and downs that came from the entire Kardashian clan, every sibling of the family welcomed a bundle of joy (or a few) since the beginning of the series — except for Kendall Jenner.

The first of Kris Jenner's 10 grandchildren was Mason Dash Disick. Fans may remember Kourtney Kardashian revealing the accidental pregnancy with Scott Disick in Miami to an unhappy Khloé Kardashian, who at the time hated Scott. Who would've thought that party girl Kourtney would seemingly swap personalities, becoming the mom of the sisters and welcoming her second child Penelope Scotland Disick just three years later? Since then, Kourtney and Scott also welcomed their youngest, Reign Aston Disick, in 2014.

Kim Kardashian now leads her siblings with the most children, having four kids within six years. First to come was North West, who even played a role in her parents destination wedding. North, Saint, Chicago, and Psalm have already made headlines for their unique names, but what would you expect for the children of Kimye?

Sisters Khloé Kardashian and Kylie Jenner took on pregnancy together, welcoming their daughters True Thompson and Stormi Webster respectively just months apart. Rob Kardashian also welcomed a child, his daughter with Blac Chyna, Dream Kardashian (the only grandchild with the Kardashian name).

Kim Kardashian and Kylie Jenner became billionaires

When KUWTK first began, the Kardashian siblings were far from underprivileged. Born to famous lawyer Robert Kardashian, each child already had quite the fortune. Plus, their mother Kris Jenner was married to a famous Olympian. Regardless, fans watched the siblings go from owning their family boutiques in Calabasas to multi-million and billionaires.

From countless club appearances to various promo deals, each member of the Kardashian clan has made quite the fortune thanks to simply being famous (plus their momager Kris takes home 10%). The family's income comes not only from starring in their E! series, but also multiple spin-off shows throughout the years like Kourtney and Khloe Take Miami, I Am Cait, Life With Kylie, Khloe and Lamar, Rob and Chyna, and others. Older sisters Kourtney, Kim, and Khloé Kardashian are all executive producers of KUWTK, alongside their momager, sprucing up their paychecks. Yet, it's the siblings businesses that seem to be bringing in the dough. 

Khloé owns her own line, Good American, while Kourtney dishes on lifestyle tips with her brand, Poosh. Rob Kardashian began his own sock line, Arthur George, and Kendall Jenner (in addition to her booming model career) started a line of dental hygiene products. Perhaps the most successful sisters are Kim Kardashian and Kylie Jenner. Kim reached billionaire status in 2021 with her brands SKIMS and KKW Beauty, while Kylie had the biggest transformation, becoming the family's first billionaire thanks to her ultra-popular Kylie Cosmetics line (via Forbes).

Kim Kardashian is studying to become a lawyer

Aside from making billions of dollars, Kim Kardashian went from rich, young socialite to businesswoman and mother on the verge of becoming a lawyer in just 20 seasons of reality television.

In a Vogue interview, Kim revealed her journey to become a lawyer was largely influenced by her late father Robert Kardashian and her success in getting President Donald Trump to grant clemency to Alice Marie Johnson, a woman who was in prison for a nonviolent drug charge for nearly two decades. The reality star first learned Johnson's story via social media, and with the help of her own lawyers, was able to set up a meeting in the White House to advocate for Johnson's release. Kim, in the meantime, began studying in a four-year law apprenticeship.

"I'm sitting in the Roosevelt Room with, like, a judge who had sentenced criminals and a lot of really powerful people and I just sat there, like, Oh, s**t. I need to know more," she told Vogue. "It's never one person who gets things done; it's always a collective of people, and I've always known my role, but I just felt like I wanted to be able to fight for people who have paid their dues to society. I just felt like the system could be so different, and I wanted to fight to fix it, and if I knew more, I could do more."

Post-KUWTK life might mean Kim adds "lawyer" to her résumé.