From the sex tape that started it all to the recent Tristan/Jordyn cheating mess.

In the little over a decade that the Kardashian-Jenners have been in the public eye, members of the fam have been involved in, well, numerous scandals. It’s just part of being a Kardashian, like contouring or shilling gummy hair vitamins or wearing Pablo T-shirts. Here, a selection of some of their most memorable controversies.

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2007: Kim’s Sex Tape

The Kardashian scandal that started it all! In 2002, Kim Kardashian made a sex tape with her then-boyfriend Ray J (seen here with Kim in 2006). In 2007, Vivid Entertainment released the tape as Kim Kardashian Superstar. Kim initially tried to stop the release of the tape but eventually settled for a reported $5 million. According to TMZ, the video has been watched more than 200 million times.

2010: The Kardashian Kard

In 2010, Kourtney, Kim, and Khloé introduced the Kardashian Kard, a prepaid credit card produced in collaboration with Mastercard. Unfortunately, the Kard came with a ton of fees, which wasn’t a great look for something targeted at teens and young adults. Less than a month later, the Kard enterprise was shut down for good.

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2011: Kim’s 72-Day Marriage

The sex tape might have started the empire, but this is the one that forced your dad to learn Kim’s name. Kim started dating NBA player Kris Humphries in 2010; they got engaged in May 2011 and married in August. The ceremony aired on E! in early October, but on October 31, Kim filed for divorce. It was a PR low point for the family, who were accused of staging the entire event as a publicity stunt. (The divorce was not finalized until 2013.)

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2012: The QuickTrim Lawsuit

Before they got deals with companies like Balmain and Calvin Klein, the Kardashians shilled for diet pill company QuickTrim (this photo is from a 2010 in-store appearance). In 2012, Kim, Khloé, and Kourtney were named in a $5 million lawsuit against the company that alleged the marketing advertised “misleading” results; the case was settled in 2013.

The Biggest Kardashian-Jenner Scandals of All Time

Here, in case your eyeballs are already getting a lil tired from reading.

2014: Khloé’s Headdress

In 2014, the family threw a Coachella-themed birthday party for North West called Kidchella. Khloé decided to wear a Native American headdress to the event, which did not go over well with representatives from various Native American communities.

2014: Kylie and Tyga’s Whole Thing

By the time Kylie and Tyga broke up for good in 2017, he’d become a fixture at family events, but their relationship didn’t have such a low-key start. Dating rumors about the pair started (1) before Kylie was 18 and (2) very shortly after Tyga called off his engagement to Blac Chyna. In 2015, after Kylie turned 18, they became more official on Instagram, and Kylie starred in Tyga’s video for “Stimulated.”

2015: Khloé’s Niqab

While visiting Dubai in 2015, Khloé posted this photo of herself wearing a niqab, a traditional face covering worn by some Muslim women. Commenters immediately began questioning Khloé’s decision to wear the niqab; she later asked two Dash employees about the incident on an episode of Keeping Up With the Kardashians and got a lesson in cultural appropriation.

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2015: Kylie’s Wheelchair Shoot

For an Interview magazine spread shot by Steven Klein, Kylie posed in a wheelchair. Critics of the cover, some who use wheelchairs in their real lives, took to social media to express their displeasure with the photos, but the magazine defended the shoot as an homage to the artist Allen Jones.

2015: Rob’s Gone Girl Instagram

This one’s just the best. During one of his self-imposed exiles from the family, Rob posted this image of Amy from Gone Girl—a character who fakes her own death and frames her husband for murder—and said this was his sister Kim, “the bitch from Gone Girl.” Kim said Rob thought he was being funny, which, sure. It must be water under the bridge now, though, because in 2017, Rob gave Kim a pair of “Gone Girl” socks.

2015: Kylie and Vlada Haggerty

Kylie’s cosmetics company has grown exponentially since she launched it with her Lip Kits in 2015, but things haven’t always been smooth sailing. In 2015, makeup artist Vlada Haggerty accused Kylie of copying her designs for some of the Lip Kit advertising. It happened again in 2016 (as seen in the Instagram here), but in 2017, Vlada wrote on Instagram that the issue had been resolved.

2015: Kim’s Morning Sickness #Sponcon

Kim has been very open about how much she struggled during her pregnancies, and in 2015, she started promoting a morning-sickness drug called Diclegis on Instagram. The FDA asked her to recall the post, though, because she failed to include information about potential risks. She was still shilling for Diclegis as recently as 2017, but with the now-mandatory designation of “#ad.”

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2015: Kylie’s Lip Fillers

It’s hard to remember now, but there was a time when Kylie swore up and down that her lips were that huge thanks to a simple combination of nature and over-lining. Finally, in 2015, she admitted that she’d tried “temporary” lip fillers, and in 2016 talked more about the sometimes painful procedure.

2016: Kendall’s Ballerina Shoot

When Vogue Spain asked Kendall to be on their cover in 2016, they also asked her to do a video shoot where she pretended to be a ballerina. This did not go over well with real ballerinas, who didn’t appreciate the implication that anyone can do something that requires hours and hours of training and practice.

2016: Kim’s “Boxer Braids”

Back in 2016, Kim and some of the other Kardashians were obsessed with a hairstyle they called “boxer braids.” Cultural critics were quick to point out that these were really cornrows, a hairstyle that was certainly not invented by the Kardashians. It was one of many times Kim and co. faced criticism for taking credit for a trend they did not create or popularize.

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2016: #KimExposedTaylorParty

Depending on how you feel about Taylor Swift, this is either a scandal or a high point in American pop culture, but the gist is this: Taylor claimed she didn’t give Kanye approval for the “Famous” lyrics, then Kim came through with receipts in the form of a Snapchat video. Whether you believe Kim or Taylor’s side of the story, the lesson is the same: Don’t get on Kim’s bad side.

2016: Kylie’s Copied Coachella Outfit

Another year, another Kylie copying scandal. After Kylie wore this look to a Coachella event, an Australian designer named Brit Day accused her of taking “inspiration” from her without permission or attribution and shared a photo of herself in the same outfit with the same rainbow braids.

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2017: Caitlyn’s Affiliation With Donald Trump

Despite being a member of a community that gets no love from the GOP, Caitlyn has never given up her interest in the Republican party. She was pro–Ted Cruz during the 2016 primaries but threw her weight behind Trump once he became the nominee, and in 2017, attended events surrounding his inauguration. (She has since sort of come around, and in 2018, finally admitted that the current administration has a terrible record on transgender issues.)

2017: Kendall’s Pepsi Ad

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Surely you remember this one. Kendall starred in an ad that presented Pepsi as the cure for all the world’s ills, amid widespread national protests against police shootings and police violence. Pepsi pulled the ad almost immediately and apologized to Kendall for involving her; Kendall later addressed the incident on KUWTK.

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2017: Kendall’s Fyre Festival Promotion

Kendall had a rough 2017, but maybe not as rough as the people who started the Fyre Festival, a failed music festival that was supposed to be luxurious but ended up turning out kind of like The Hunger Games. Kendall was initially involved in promoting the event via Instagram (as was her friend Bella Hadid, plus a handful of other top models) but deleted the posts after the whole thing turned out to be a bust.

2017: Kylie’s Camo

After Kylie released a new line of camo clothing, PluggedNYC designer Tizita Balemlay claimed that Kylie ripped off her designs. She also alleged that Kylie’s stylist had requested samples of PluggedNYC looks.

2017: Kendall and Kylie’s Biggie Shirts

For some reason, Kylie and Kendall decided it would be a good idea to release a Kendall + Kylie T-shirt line featuring their faces superimposed over photos of deceased rappers Tupac Shakur and Notorious B.I.G. No one liked this, least of all Biggie’s mother Voletta Wallace, who said no one from the estate had been contacted. The sisters apologized, and in 2018, a lawsuit about the use of the Tupac photo was dropped.

2017: Kim’s Defense of Jeffree Star

First, makeup artist Jeffree Star criticized Kim’s KKW Beauty line. Then, some Kim fans came at him for coming at her, but then others reminded those fans that Jeffree had said some racist things in his past. Kim was apparently unaware of these things and defended him on Snapchat, which led Kim fans to wonder why she was defending a controversial figure like Jeffree. She then sort of apologized, saying that she thinks he deserves to be forgiven for his past.

2017: Kim’s Blackface Allegations

When KKW Beauty launched in 2017, the first round of ads (the version to the left came after the backlash) featured Kim with a much darker complexion than she normally has, leading Twitter users to accuse her of intentionally darkening her skin tone. Kim later said she never meant to offend and thought the problem was caused by bad contrast.

2017: Kim’s Aaliyah Halloween Costume

One of Kim’s Halloween costumes in 2017 (yes, she wore several) was Aaliyah in the “Try Again” music video. While the fashion portion of the look was well-executed, the costume drew criticism because it involved Kim, who is not black, dressing up like a black woman. Kim apologized by saying that she and her family “don’t see color.”

2017: Rob’s Revenge Porn

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Rob’s relationship with Blac Chyna was a constant roller coaster of drama, but the low point came when Rob shared intimate photos of Chyna on Instagram as “payback” and claimed that she’d been cheating on him. Chyna responded by saying that Rob hit her during their relationship. They still publicly squabble from time to time, but they did reach a custody agreement in 2017.

2018: Kim’s “Bo Derek” Braids

Yep, it’s another cultural appropriation controversy! Having not learned her lesson after the “boxer braids” incident, Kim wore Fulani braids in January and called them “Bo Derek” braids, which, again, did not go over well because she’s…wrong.

2018: Khloé’s “Khlo-C-D” Videos

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When Khloé’s Khloé With a K app launched in 2015, it featured a video series called “Khlo-C-D,” where she showcased her impressive organizational skills—stacked Oreos, many different kinds of pickles and jars, etc. A few years later, in 2018, people with actual OCD began to call her out for the title of the video series, which is, you know, riffing on a very real disorder. BTW, the Kardashians announced in late 2018 that they would be shutting down their apps in 2019. Sad.

2018: Kourtney’s Mason-Shot Thirst Trap

Kourtney is far and away the least controversial Kardashian sister, but she was still bound to pop up on this list somewhere. This sexy photo was taken by her 8-year-old son Mason, which is either impressive or weird. Also weird? The time Kim posted a topless picture taken by North.

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2018: Khloé’s Cheating Boyfriend

If you haven’t heard about this one, (1) please invite me to your cave; it sounds nice and quiet there and (2) read this to catch up. TL;DR: Tristan got caught on camera (yep, there’s video) cheating on Khloé with multiple women, just days before she was due to give birth. Yeah, not a good look.

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2018: Kim’s Cornrows, Again

Oops, she did it again! This time at the MTV Movie and TV Awards. Some things never change, I guess.

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2018: Kendall’s Modeling Comments

In an interview with LOVE Magazine, Kendall said that she was “super selective” about which runway shows she chooses to model for and “was never one of those girls who would do like 30 shows a season or whatever the f*ck those girls do.” Other models, who don’t share the same financial privileges that Kendall has grown up with, weren’t too happy with Kenny for that little tidbit.

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2018: Kim’s Ecstasy Bombshell

In an episode of KUWTK, Kim admitted that she used to do ecstasy when she was younger. She specifically ID’ed two noteworthy moments in her life when she was under the influence: when she married Damon Thomas and when she filmed her sex tape with Ray J.

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2019: Kendall’s Disappointing Announcement

Kris stirred up a whole lotta drama when she told her Twitter followers that something big was about to happen with Kendall. “Prepared to be moved,” she wrote with v dramatic hashtags like #BeTheChange and #authenticity. But when the announcement turned out to be a Proactiv sponsorship, Twitter completely dragged both of them.

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2019: Kim’s Fast Fashion Debacle

Fast fashion sites like Missguided and Fashion Nova have been ripping off the Kardashian-Jenners’ clothes for years, but some people started to suspect that Kim was secretly in on the copycat looks. After Diet Prada accused Kim of giving certain brands previews of her designer getups, she hit back by denying the rumor and even suing Missguided for using her image for their knockoffs.

2019: Khloé’s Cheating Boyfriend…Again

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Is “once a cheater, always a cheater” really true? It seems like, when it comes to Tristan at least, the adage is definitely true. In mid February of this year, news broke that Tristan had locked lips with Kylie’s BFF, Jordyn Woods, while at a party at his house. Jordyn insisted that it was a harmless, drunken peck, but Khloé (and Jeffree Star) thought otherwise.