The new ABC News special covers everything from Caitlyn's transition to earning respect in the industry, privacy, anxiety, and the ever-expanding Kardashian business empire.
Just when you thought there wasn't anything more to learn about the Kardashians, ABC News' Robin Roberts got into it with almost every member of the sprawling clan. The only ones not interviewed were Kylie and Rob, though the latter largely avoids the spotlight at this time.
There was plenty to talk about, though, with Kris and Kendall Jenner and the Kardashian sisters, Kim, Khloe and Kourtney. With the family heading into its newest iteration on Hulu with "The Kardashians," Roberts asked Kris what's new or different about this show?
It remains to be seen if the structure of the show will evolve, but for Kris, the biggest change is in the family itself. "I think we just evolved, you know?" she responded. "We’re all growing up and the kids are a decade-and-a-half older, and this is a new chapter."
The ladies tore down the walls to talk about everything from Kris being the driving force of the family empire in its early days to how Kylie actually took the lead as they expanded into their separate business empires.
Khloe talked about her relationship struggles, as well as the struggles she's faced over the year with the concept of beauty and how she never quite felt she fit in. It's something Kim echoed, having come up in an era she described as "'90s waif," where slim and blonde were the ideal.
She was essentially describing her one-time BFF and boss Paris Hilton, with a TMZ photographer taking at least partial credit for her rise to fame once Kim started to hang out and be seen -- and photographed -- publicly with Paris.
"I would have done anything to be famous," Kim admitted. "I’m so open and honest about the fact that I loved being famous. Some people are made for it better than others. I would be lying if I said I didn’t feel like I could handle it, if I didn’t think I was made for it."
She credited being young and impressionable at ten years old when MTV's "The Real World" came out, the first breakthrough reality show. Suddenly, she saw people being famous just for opening up their lives and being genuine in a way that had never really been seen before.
Kim was able to follow Hilton's template, warts and all to fame, though she paid a partial price for a while because of it. Like Paris, Kim partly rode on the heels of intrigue caused by a sex tape scandal to her reality TV fame. But it didn't open doors as many might think.
"I’ve been in this business for 20 years and being on a reality show has not opened up doors for me in the way people would assume. If anything, being on a reality show, and let alone a reality show and a girl with a sex tape, I mean all the doors closed for me," Kim said. "I was completely not respected. So I felt like I had to work extra hard to get a little credibility."
Working right alongside her was momager extraordinaire Kris Jenner. In an interview dated 2010, Caitlyn said that Kris cut her teeth working on Caitlyn's post-Olympics publicity career, which was a tremendous success. It was through this work that Kris became the business mastermind she is today.
Kim's ambition -- and that sex tape fascination -- may have been the catalyst, but it was Kris who was savvy enough to leverage that into an outlet for the entire family to become superstars.
Kourtney spoke about how much she learned about business just watching how hard Kris worked and hustled, and how organized she was in keeping it all straight and the machine moving forward.
"Watching the way she organized her life -- she always had a rolodex -- the way she had her filing systems; it’s down to little things like that," said Kourtney. "You may not even recognize at the time what an impact it had, but it helped give you the motivation to do it."
"My mom believed in us more than anyone else," Khloe said. "It’s because of her, she fought for us to be where we are."
For Kris, it's a bit of a dance navigating and managing the ever-expanding Kardashian empire. "Every single child is so different and has different ideas, energy, strengths, weaknesses," she said. "It’s learning when to lean in, learning when to let go, learning when to take over, learning when to say, ‘I give up.’"
It may have been Kris who helped build the family to a certain level of success, but it was surprisingly the baby of the bunch, Kylie, who figured out how to take the whole operation to the next level.
She was able to take full advantage of the privilege she was basically born into, having grown up on "KUWTK," and utilize that to expand into her own business, with Kylie Cosmetics and her signature lip kits.
"I said, when’s the marketing campaign? She said, what marketing campaign?" Kris laughed, remembering when Kylie was just launching her business. "Mom, I know what I’m doing."
And she did, with Kris marveling that "she launched her product one morning and four seconds later it was gone. So they know what they're doing." There's still no one like Kris at negotiating a shrewd business deal, but it was Kylie who innovated the idea of the family creating its own brands, instead of brand partnerships.
Suddenly, Kim has KKW Beauty and SKIMS, Khloe has Good American and Kourtney has her Poosh lifestyle brand. Each of them are in different lanes built on the passions of the individual women involved, which Kris emphasized as a key to their success.
And each of them has a lot to do with the beauty market and effectively redefining and expanding the definition of beauty.
Kim Kardashian almost single-handedly evolved American interest in that "'90s waif" look to her signature curves, but it wasn't an easy evolution for her. "I never felt the inclusivity growing up," she explained. "Everyone was blonde and tall and thin and I never really connected with anyone."
That was a huge part of her impetus to launch SKIMS, "because I wanted a line that had no boundaries."
"I think everyone deserves to feel exactly how they want to feel and praised exactly how they are," she continued. "And if that isn’t up to anyone’s standards, or a specific beauty standard, than f--- them. I don’t know how else to say it."
Khloe has had an even more complicated relationship with beauty standards, scrutinized and compared negatively while in the public eye.
She admitted to weight fluctuations her entire life, and that fashion didn't always seem to want to deal with her at a size 12 or 14. That was why she got involved with Good American.
"I wanted to be in bodycon clothes, I wanted to be in things that were skintight, but in the fashion world it was kind of like, ‘Here’s a mumu, and be quiet. You know, that’s your size,'" she said. "And I didn’t want to settle for that."
Khloe has been pretty open and public about her struggles in the public eye, with the cruel comments she's received over the years regarding her appearance. As such, she admitted to having some cosmetic surgery to help find her confidence.
"My whole life, I would always say I’ve wanted my nose done, like forever," she said. "But it’s in the middle of your face and it’s scary to think about. But, I finally got the courage and I did it and I love it."
"My only regret is that I didn't do it sooner," she added.
Khloe has embraced a body transformation to help grow her confidence, and she's not the only one. Kylie notably changed her thinner lips to create the plump, pout she's become famous for. And she's been open about how she managed it.
Meanwhile, other members of the family have taken different approaches. Brother Rob featured heavily in earlier seasons of the show, but the stress and anxiety of being on-camera finally reached a breaking point with him and he's been seen sparingly since then.
Kourtney has been very vocal about managing and controlling how much of herself she's willing to give to the cameras and the show for the sake of her own mental health and the privacy of her kids.
"I think it’s nice to, like, not even see. I have this new thing where I do not look at my phone until after I’ve dropped off my kids," said Kourtney, explaining how she keeps at least part of her life separate from the family empire.
As for Kendall, the other junior member of the family who grew up with omnipresent cameras and global fame, she's talked openly about her own struggles with anxiety, and how the family's fame has impacted her.
"Personally, what’s affected my anxiety the most is the amount of negativity that I see," she said. "There’s just literally too much."
Kris responded as a mom first and a manager second, prioritizing her daughter's health and happiness. "When she was out on her own, she struggled with being anxious and slowly but surely we learned how to create her boundaries and how to do what she could handle," Kris said.
Kendall remains a part of the Kardashians empire, with a larger on-screen presence than her older brother, but she's still far more enigmatic and private in her personal life than the rest of her sisters.
"I think at the end of the day all of us just aspire to blissfulness, we want to be happy and we want to feel safe," said Khloe.
One area they've very publicly struggled with finding that happiness and that feeling of safety has been in personal relationships. Even Kris was not immune to them after Caitlyn first came out as transgender and transitioned into a woman.
That said, Kris said that the former spouses are good now. "We’re fine. We’re friends. I see her when she’s at a family thing, so it’s settled down a lot," she said.
Kris described Caitlyn's coming out and transition as a "big shock," saying it was "a scary thing to go through because you know nothing about it."
"It’s a subject I never thought I would ever have to directly deal with, confront, be understanding about something that I didn’t understand," she said.
Khloe has had her own relationship struggles, unfortunately having to deal with infidelity, including from the father of her child -- more than once. And yet, she said Tristan Thompson did make her "feel incredibly safe in the beginning."
She recalled the decision she made to allow him in the delivery room right after finding out he'd cheated on her right before giving birth -- but she was doing that for their child. And even through everything, including him cheating on her again and getting another woman pregnant during an attempted reconciliation, she still had kind words for him.
"I still think he’s a great guy, he’s a great dad, he’s just not the guy for me," she said.
And then there's Kim's relationship situation, which has been playing out a lot more in the public eye than she would have liked. After years of marriage and four kids, Kim is in the process of divorcing Kanye West, and it's not been going very smoothly.
Kanye has been publicly blasting her and new boyfriend Pete Davidson on social media, and even in his music videos. At the same time, he's been trying to win her back. It's been a bit chaotic and a lot stressful for both Kim and Pete.
"You want to take the high road and sometimes it’s hard," she admitted. "But I think that at the end of the day, everyone has their own way of communicating. I’ve always been a champion of him speaking his truth and I would always want that."
She said she's been "open and honest" with her older kids about everything. At the same time, she said, "I want my kids to be happy and healthy and think the world of their dad. And they do."
As for Pete, Kim seemed to hint that this is more than just a casual thing. "I am a relationship kind of girl, for sure," she said. "And I wouldn't be with someone if I didn't plan on spending a lot of my time with them."
She did say that she wants to take her time, and for good reason, but that she's "very happy and very content," adding that "it's such a good feeling just to be at peace.
While Kim's relationship status is definitely in the "it's complicated" category, big sister Kourtney's relationship is still in its "hot and heavy" phase. And yet, Kourtney still can't even believe it happened between her and Travis Barker, admitting she thought it could destroy their relationship entirely if it went romantic.
"It’s so funny when we think about, this is us, can you believe it?" Kourtney mused. "We’re like Kourtney and Travis, who are friends." It's because of their long friendship that Kourtney would have never expected it to turn serious, thinking it could actually destroy that friendship.
Instead, their love has grown by leaps and bounds to the point Travis is the first man she actually wanted to marry, agreeing to his proposal and making it official. They even went for a trial run recently with a wedding ceremony (sans certificate) in Las Vegas after the Grammys.
The family has made it clear that all of their relationship drama, as well as all the other facets of their busy lives, will play out on their new show, including Travis and Kourtney's dramatic proposal and the entirety of Kim and Pete's relationship from when they met late 2021 on the set of "Saturday Night Live" when Kim hosted.
Fans will finally get to see it all -- including what's different and what's the same -- as the first family of reality television becomes the first family of streaming with the premiere of "The Kardashians," April 14 on Hulu.