The Most Revealing Kardashian Moments On TV

England has the Royal Family, and we have the Kardashians. While they're far from royalty, in today's pop culture they are treated as such. The Kardashian-Jenner clan is arguably the most famous family in the country, and whether you like them or not, you know who they are. The family was first introduced to viewers in 2007 when their hit show "Keeping Up with the Kardashians" launched on E! They've shared their lives with the world for nearly two decades, creating a billion-dollar empire with reality television and multiple businesses. Though they are often criticized for having no talent, they have captivated pop culture ever since they became relevant. 

Sex tapes, cheating scandals, babies, marriages, divorces — the Kardashians have never shied away from baring it all on television. We've watched them grow over the years, becoming designers, entrepreneurs, models, and fashion moguls. While they can't sing or dance, some argue that it takes a certain amount of talent for the family to have reached such great heights off of reality television. Part of their appeal is just how open they are to viewers, letting us into their private lives and never holding back. 

While the family has weathered countless controversies, one thing remains the same: The Kardashians have continued to remain a united front through all the ups and downs they've confronted over the years. Some of the family's most raw and shocking moments have been captured by cameras, and we are breaking down the most revealing Kardashian moments on TV.

No one could forget Kim Kardashian's 72-day marriage. Though the SKIMS founder has managed to weather her fair share of controversy over the years, nothing was quite as explosive as the tabloid firestorm surrounding her divorce from Kris Humphries. Kardashian met the NBA star in 2010 after being introduced to him by a mutual friend. The pair got married the following year, and their extravagant wedding had its own E! spin-off special titled "Kim's Fairytale Wedding."

Their honeymoon phase ended just about as quickly as it began, however, as fans got a glimpse into just how tumultuous their relationship was on "Kourtney & Kim Take New York." In a clip from the spin-off show, Kim is seen breaking down in tears over the lack of connection she had with the athlete. The "Kim Crying Face Meme" was even born from the infamous clip after it went viral. "He's everything on paper exactly what I want in someone, but for some reason, my heart isn't connecting," Kim tells Kourtney in the video. 

Ultimately Kim and Humphries' marriage ended in October 2011 after the KKW Beauty founder filed for divorce. At the time, the basketball player released his own statement saying: "I love my wife and am devastated to learn she filed for divorce," adding, "I'm willing to do whatever it takes to make it work." The former NBA player filed for an annulment of the marriage a month later, but he later dropped the request and their divorce was settled in 2013. 

One of the most shocking moments ever featured on "Keeping Up with the Kardashians" was Caitlyn Jenner's transition. The Olympic gold medalist debuted as a transgender woman in 2015 on the cover of Vanity Fair and the aftermath was heavily featured on the Kardashians' reality show. Jenner and Kris were married for over two decades, and share biological kids, Kylie and Kendall, as well as Kris' four other children from her ex-husband, the late Robert Kardashian. News of Caitlyn's coming out story came just a year after she and Kris finalized their divorce in 2014. 

Caitlyn took some digs at her ex-wife in the interview, saying their marriage woes were "20 percent gender and 80 percent the way I was treated." Kris didn't take too kindly to being called out, and the momager's mixed feelings for her former husband were a focal point in the E! series following Caitlyn's transformation. In a clip of an emotional conversation between the former spouses, Caitlyn told Kris: "You are the toughest one to talk to out of anybody, okay?" to which Kris replied, "Well maybe it's because I'm the one you lied to the longest." Kris went on to say, "It's like I have to mourn Bruce Jenner because I feel like you died."

Khloe and Kim's relationship with their former stepdad is strained to say the least. The sisters admitted in a 2022 episode of "KUKTK" that while there's no beef, they speak to their stepdad only every once in a while. As of the time of writing, Caitlyn is dating Sophia Hutchins, who is nearly 50 years younger than her. 

No relationship was quite as on-again-off-again on "Keeping Up with the Kardashians" than the one between Kourtney Kardashian and Scott Disick. The pair first met in 2006 after running into each other at a party in Mexico and went on to date for nearly a decade before splitting in 2015. The pair, who have three children together, have weathered their fair share of controversy over the decade that their lives have been featured on reality television. Kourtney's distrust in her former partner often stemmed from multiple cheating accusations. 

The first evidence against Lord Disick was revealed in 2008 when the Poosh founder read texts off of Disick's phone sent from a contact named "my wife." In the Season 2 premiere of "KUWTK," Kourtney admitted: "I cannot believe Scott could have cheated on me. I'm sick to my stomach that this could have happened." The two ultimately split up and got back together for several years, weathering reports of Disick's alleged cheating throughout the years.

One of the most revealing moments on the reality show involved Kim playing detective and kicking a woman out of Disick's suite. In a clip from Season 13, after finding the mystery woman in a bathroom, Kim yells, "What the f*d*k are you doing here?" adding, "Seriously, you're just like a f**king whore." She continued to yell at the woman, adding, "Get your s–t and security will escort you the f–k out of here!" 

Kim shared in the episode that at the time of the controversy the Talentless founder was attempting to reconcile with Kourtney.

Kanye West goes to great lengths to protect the ones he loves. During Season 1 of the Hulu series "Kardashians," the rapper made a cross-country trip to meet up with Kim Kardashian's ex-boyfriend Ray-J and retrieve footage of their alleged sex tape. In the episode, the incident began when reports surfaced that Ray-J's manager Wack100 had a copy of an alleged second sex tape featuring Kim and Ray-J (Kim and Ray-J were famously involved in a sex tape first released in 2007). "Kanye, holla at me, bro," the manager said on the Bootleg Kev podcast, "We got part two on the laptop. Ain't never been seen. We'd love for you to have it."

Tensions rose when the SKIMS founder's son, Saint, found an ad for part two of the alleged intimate video while playing Roblox online. After breaking down in tears over the potential existence of another tape, which Kim said she believed didn't exist, Kanye flew to meet up with Ray-J and retrieve the footage. "I know Kanye did this for me but he also did this for my kids," Kim said in the episode, adding, "I want to shield them from as much as I can ... like that is just the most important thing to me ... " 

Kim also claimed in the episode, as reported by Buzzfeed, that there was no second sex tape on the laptop. "It was just footage of us at a restaurant, at a nightclub — nothing sexual, nothing weird," she said.

One of the most intimate moments on "Keeping Up with the Kardashians" was the breakdown of Kim Kardashian's marriage to Kanye West. The pair's entire romantic relationship was captured by reality television cameras, from the proposal at the San Francisco Giants baseball stadium to their divorce being finalized in 2022. While their nearly decade-long relationship had its fair share of ups and downs, the stars, who share four children together, became one of the most talked about couples in Hollywood. Their split in 2021 dominated the news cycle, and Kim opened up about the publicized breakup while filming the family's former E! reality show.

During part one of the series finale of "KUWTK," as recapped by L'Officiel, the KKW Beauty founder breaks down to her sister Khloe while in the midst of her divorce proceedings. "I honestly can't do this anymore," she said, adding, "Why am I still in this like, place where I'm stuck for years? Like, he goes and moves to a different state, every year, I have to be together so I can raise the kids, you know? And he's an amazing dad, he's done an amazing job." 

At the time, Kim and Kanye were living separately, with Kanye at his ranch in Wyoming and Kim staying in Los Angeles. Kim continued to get emotional in the episode, admitting: "I feel like a f**king failure, that it's like, a third f**king marriage," adding, "Yeah, I feel like a f**king loser. But I can't even think about that like, I want to be happy."

Kim Kardashian is known to speak her mind. While the reality star is used to opening up about her personal life to the rest of the world, fans were in for a surprise during Season 1 of "The Kardashians." The mother of four revealed in an episode of the Hulu series that she had sex in front of a fireplace with Pete Davidson in honor of her grandmother. "My grandma told me that you really live life when you have sex in front of the fireplace," Kardashian said in the clip, adding, "and so we had sex in front of the fireplace in honor of you." 

Her grandmother, who goes by MJ, laughed off the revelation, asking the SKIMS founder if it was in the lobby of the hotel she and the comedian were staying in. "Not in the lobby!" Kardashian responded. "But how creepy to think about your grandma before you have sex?"

MJ took the strange honor in stride, going on to say, "I know, but I was younger once. I was younger once." The KKW Beauty founder and the former "Saturday Night Live" cast member first got together after Kardashian starred as the host of "SNL" in 2021. After an unexpected whirlwind romance, full of publicized jabs between Kanye West and the comedian, the pair called it quits nearly a year later in November 2022. 

Kris Jenner revealed that she had a shocking affair that led to the end of her marriage with her ex-husband, the late Robert Kardashian. What's even more scandalous is that the matriarch of the Kardashian clan met up with the man in question while filming "Keeping Up with the Kardashians." The controversy first ignited when Jenner admitted to having the affair in her memoir "Kris Jenner ... And All Things Kardashian," according to Mirror. The momager named the mystery man Ryan and admitted: "It made me feel young, attractive, sexy, and alive. Along with these feelings came a wave of nausea. I actually wanted to throw up at the same time. Because it dawned on me that I had not felt that way with Robert for years."

Jenner's mystery man eventually came forward as Todd Waterman. The former professional soccer player revealed to the Daily Mail that he was the other man in Jenner's marriage. The former flames crossed paths again decades after their affair, and the aftermath was featured on an episode of "KUWTK" that premiered in 2012. In the episode, shared by People, after Kim finds out her mom exchanged emails with Waterman, she asked her, "Do you want to still be married?" continuing, "Then stay far away from him. He already ruined your first marriage. Seriously." 

After their first run-in, Jenner did ultimately meet up with Waterman again on an episode of "KUWTK," against the wishes of her ex-husband and children.

Sisters fight hard and love hard — and the saying couldn't be truer for Kim and Kourtney Kardashian. The reality stars took their heated discussion a step further, however, when the two got into a physical altercation in a Season 18 episode of "Keeping Up with the Kardashians." The fight started after Kim, Kourtney, Khloe, and Kendall Jenner were having a conversation about Kylie being too sick to participate in a Paris fashion show. In the clip, Kim tells her sister: "If I were on my deathbed, I would still show up," adding, "Mom is so used to ... me and Khloe, whenever[, even] if we're sick... [Kourtney] You don't care about stuff."

Kourtney responded to the dig saying: "You act like I don't do sh**. You have this narrative in your mind. No, no, no, I will literally f*** you up if you mention it again." Kourtney then started getting physical with Kim, which lead to a pushing match and ended with Kim slapping her sister twice. Khloe had to physically separate the two sisters during the fight. 

During the Season 18 reunion special, per Insider, Kris admitted she didn't want the scene to air, but ultimately the Kardashian-Jenner clan collectively decided to run the footage. Shortly after footage of the altercation aired in 2020, Kourtney took a break from the show. That same year, the Kardashian family announced that the season would be the last of "KUWTK." The family ultimately made a deal for their Hulu series "The Kardashians" which premiered in 2022.

Kourtney and Kim Kardashian have had their fair share of beef over the years, and on Season 3 of "The Kardashians," the sisters were on the outs again. This time, however, it was Dolce and Gabbana that led to their rift. The controversy began after Kim curated a Dolce and Gabbana collection for Milan Fashion Week in 2022. The SKIMS founder was in charge of putting together nearly 100 looks for the show, pulling from the fashion designer's '90s archives. 

The show debuted just months after Kourtney's wedding to Travis Barker in Italy, in which Dolce and Gabbana personally designed looks for her '90s-themed wedding. "Kourtney and Travis just worked with [Domenico] Dolce and that was her whole vibe of her wedding. Then after the wedding, I got a call saying they wanted me to creative direct their fashion show in Milan. I think this is such a good opportunity that I don't want to pass this up," Kim said during the Season 3 premiere, per Us Weekly. 

Kourtney revealed in the episode that "It isn't about business. There is just so much and it takes precedence over hurting your sister. It is legit copying my wedding." The Poosh founder also said, "It is just stupid because it is a deeper thing than that. It is about [where people] are grabbing whatever is in the way. It is such an abundance and an excess — it is never enough. It is never OK to just not do something or turn something down."

When it comes to scandals, Tristan Thompson has seen plenty. The former NBA star has caused controversy after controversy after being caught in multiple cheating scandals while dating Khloe Kardashian. The pair met in 2016, and ever since they started dating that year, Thompson's infidelity caused a strain on their relationship. 

Kardashian and Thompson, who share two children together, have split up a few times over the course of their time together. However, during one of their reconciliations, a huge cheating bombshell was dropped during the Season 1 finale of "The Kardashians." During the episode, Kim breaks the news to Khloé that Thompson had fathered a child with another woman, after finding the news on the internet. At the time, Khloé and Thompson had just received news that they were expecting their second child via surrogate. "I find out what Tristan is doing with the rest of the world," Khloé admitted: "A courtesy would be not doing it. But fine, if you do it, you're not even gonna [give me] a f—ing heads up before the rest of the world? It's just an additional slap in my face. It's humiliating, I'm embarrassed."

Thompson released a statement following the incident via his Instagram Story, shared by People, writing: "You don't deserve the way I have treated you over the years. My actions certainly have not lined up with the way I view you. I have the utmost respect and love for you. Regardless of what you may think. Again, I am so incredibly sorry."

Kylie Jenner is known for her signature pout — so much so that she's designed her entire company around it. The Kylie Cosmetics founder wasn't born with naturally voluptuous lips, however, and when fans started noticing her noticeably bigger lips in 2015, it sparked major controversy. Jenner opened up about her decision to get injections on "Keeping Up with the Kardashians," according to BuzzFeed, admitting: "I have temporary lip fillers," adding, "It's just an insecurity of mine."

The makeup mogul admitted she struggled for years with her lip insecurities. Us Weekly shared that in an episode of "Life of Kylie" in 2017 she revealed a former boyfriend told her, "I didn't think you would be a good kisser because you have such small lips." Jenner turned her insecurities into a billion-dollar business, ignoring any backlash over her puckered pout and introducing the Kylie Lip Kits line in 2015. Eventually, the line morphed into what is now known as Kylie Cosmetics, offering a complete range of makeup and skincare well beyond just lipsticks. After just a year in business, she was racking in over $300 million in profits. 

In an interview with HommeGirls, Jenner admitted: "Yeah, I love full lips and wanted full lips, but growing up I was always the most confident person in the room. I was the girl performing for everyone. I had my one lip insecurity thing, so I got lip filler, and it was the best thing I've ever done. I don't regret it. But I always thought I was cute."

Khloé Kardashian and Lamar Odom's quick courtship was a highlight of "Keeping Up with the Kardashians," especially since they tied the knot after knowing each other for just a month. The duo met in 2009 and married in the fall of that year, and their relationship was featured on their own spinoff show on E! "Khloé and Lamar," which debuted on the network in 2011 and followed the ins and outs of their life as a married couple. 

Their relationship took a turn for the worse in 2013, however, after reports surfaced about the former NBA star allegedly cheating on his then-wife. The pair split that same year after Kardashian filed for divorce, and Odom eventually revealed his infidelity led to the split. In "TMZ Presents: Lamar Odom: Sex, Drugs & Kardashians," the former professional basketball player admitted he treated his ex-wife terribly throughout their relationship, saying: "I'd have these random women coming out. Some of them all came out at one time."

The Good American founder opened up about their split in an episode of "Keeping Up with the Kardashians," admitting Odom was still wearing his wedding ring following their split. "He's now wearing his ring full time. F**ck your ring, you were wearing it when you were f**king someone too. He doesn't think we're going through with the divorce ... The way I was living is not a way to live," she revealed. Kardashian and Odom's divorce was eventually finalized in 2016.

One of the most iconic moments on "Keeping Up with the Kardashians," was Khloé Kardashian's trip to jail after being arrested in 2007. The Good American founder was arrested on DUI charges but failed to complete her alcohol education course, and was sentenced to 30 days in jail. "[My judge] thinks that my job is a luxury and that there's no excuse on why I got kicked out," the reality star admitted on an episode of "KUWTK," per E! News. 

After reporting for her sentence in 2008, Kardashian was released due to overcrowding after serving just three hours. "It's not fun. Being in there for 30 days, I would've died," she admitted in a "KUWTK" confessional. Kim, Kourtney, Kris Jenner, and Malika Michelle all rode along for the infamous car ride to drop the reality star off, in one of the most unforgettable moments on the series. During the trip, Jenner scolded Kim for taking pictures of herself, saying, "Kim would you stop taking pictures of yourself? Your sister is going to jail." 

Nearly two decades later, Khloé looks back on her short-stint in jail with laughs. On an episode of their Hulu series "The Kardashians," she and her mother joked about the experience over weed gummies. "Malika did my hair for my mugshot," Khloé said on the show. "I did my own makeup." Despite what Jenner admitted was a nice-looking mug shot, Khloé admitted she has no plans to return behind bars. "I've never been to jail since," she added. "So I've learned my lesson."

"Keeping Up with the Kardashians" fans have gotten to see incredibly intimate moments throughout the years. Some of the most revealing footage on the show has been from the multiple babies being introduced into the family. Members of the Kardashian clan have let cameras into deeply personal aspects of their lives, including filming the births of several of their children. 

When Kourtney was pregnant with her first child, Mason Disick, "KUWTK" were there to capture the moment her son entered the world. Viewers got a first-hand look at the delivery, but they didn't expect to see the reality star take matters into her own hands — literally. 

In one of the most shocking moments in the series, Kourtney reached down and pulled her son out of the birth canal herself after one of the medical personnel asked her if she wanted to grab him. While there have been many babies delivered into the Kardashian-Jenner clan, Kourtney was the only mother to pull out her own child.

One of the most iconic lines to come from the Kardashians is "Kim, there's people that are dying." True "Keeping Up with the Kardashians" fans recognize the quote from when Kourtney chastised her sister for crying over a lost diamond earring while on a family vacation. 

After breaking down in tears, Kim finds out that not all hope is lost — and neither is her diamond earring. Kylie Jenner found the giant glistening accessory shortly after it fell off in the ocean.

Ultimately, viewers were left with one of the most memorable lines ever delivered on the show, and the Kardashians were able to poke fun at the incident years later. "We are still looking for that damn diamond #KampKoko," Khloé wrote in an Instagram post in 2022 that featured her and Kim posing in bikinis at the beach. Kim also joked about the infamous earring debacle, posting an Instagram photo alongside Kourtney in the ocean in 2021, writing, "Kourtney lost her earring in the ocean so I helped her find it."

It was the end of an era. After 20 seasons and 14 years of reality television, the final season of "Keeping Up With the Kardashians" aired in 2021. While filming the season, Kim, Kourtney, Kris Jenner, and Khloé broke the news to the production crew during season 20. In the tearful conversation, Jenner told the team, "We just wanted to tell you in person that we won't be going forward with filming the show anymore. It's been a really excruciating decision to make. This journey's been the most incredible thing that we've ever done, and we can't even express the appreciation we have for you along the way."

Kim also expressed her gratitude, saying through tears, "I just want you to know that we really appreciate you guys, each and every one of you." In her confessional, Khloé admitted that members of the "KUWTK" crew even stayed with her on Christmas day after she moved to Dallas so she wouldn't be alone. "I have such a security blanket in these people," she added. In the episode, Kourtney revealed she had no regrets about sharing her life on the show. "[We've been] in each other's lives every day for 13 years," she said.

The Kardashians' career on reality television was far from over following their departure from E! network. The family announced their decision to debut their Hulu reality show "The Kardashians" at the end of 2021, and the first season premiered in 2022.