Inside Jeffree Star's rocky relationship with the Kardashian-Jenner family, from makeup feuds to a rumored affair with Kanye West

At the time, he took to social media to critique lip glosses he purchased from Kylie Cosmetics. According to Allure, Star said in a now-deleted tweet that he was "SO disappointed" in the products because they had damaged wands that he described as "unacceptable."

He added in a Snapchat video at the time that he "loved" Jenner, but felt her products should be held to a high standard.

"This is no hate whatsoever, it's just like, when you're a multi-million dollar celebrity, why would you put anything out half-assed?" Star said in the video, which has been reposted to YouTube.

"So no offense to her, but these are f------ garbage," Star said before throwing the Kylie Cosmetics lip glosses in the trash.

Shortly after Star's criticism, Kylie Cosmetics shared a lengthy post on Instagram in which Jenner said she "stopped all production and changed" the wands of her lip glosses when she noticed customer complaints. She also promised to send new lip glosses to everyone who received damaged products.

Star shared yet another statement about Jenner and her brand following the Instagram post. On Twitter, according to Allure, he wrote: "How ironic that it took ME giving an honest review, which got worldwide attention, to get Kylie Cosmetics to make a statement. I'm just glad they're finally addressing the issue and fixing it, that's all me and every customer that got those wands wanted."

Though Star has since deleted his tweet, according to Allure, he "cleared the air, making sure people knew there was no bad blood between him and Jenner" on the social-media platform.

Jenner responded to Star by tweeting the message "I have the same passion," with a yellow-heart emoji.

In a May 2016 interview with Cheryl Wischhover for Racked, Star discussed the former lip-gloss controversy, said the products "suck," and described Jenner's tweet to him as being a "half-ass" response.

When asked by Wischhover if he felt Jenner had done proper research before creating her famous lipsticks, Star replied: "No. I can already say no without you finishing the sentence. No."

"She found a lab that makes a $5 formula and they're called Colourpop," Star said. "They gave her the same exact one with her name on it and charged $20 more. I'm bored."

Racked noted that Jenner working with Colourpop was a popular theory at the time, though there was no evidence to confirm she was selling the brand's lipsticks under her brand name. Today, it's well known that Seed Beauty is a shared manufacturer behind numerous beauty brands, including Kylie Cosmetics and Colourpop.

In a July 2016 video, the makeup mogul defended his comments about Jenner's lip glosses, and once again compared her products to those created by Colourpop.

But by the following month, Star had seemingly put the past behind him.

"Now obviously I had one little bad experience with this brand," Star said in an August 2016 review of Jenner's products. "Does that mean I have to hate every product and talk s---? That's not my style."

He said he liked using one of the Kylie Cosmetics eye-shadow palettes in that video, and later went on to give Jenner's lip kits a glowing review in September 2016. He also liked the KKW x Kylie Cosmetics lipstick collaboration in April 2017, and her purple palette in October 2017.

One day after the party, which was held in Los Angeles, California, Star posted a selfie of himself with Kardashian West on Instagram, writing: "Serving you #Contour Queen realness Congrats @kimkardashian on the launch of #KKWBeauty ."

He also shared a glowing YouTube review of Kardashian West's first products the following day, and said he had met with the reality-television star both at her home and launch party to learn about the products.

"It was really cool to just have one-on-one time with her and actually hang out and talk," Star said. "I know a lot of you saw me on Kim's Snapchat and you were like 'What the hell?'"

He then added that he's a fan of Kardashian West's entrepreneurial efforts, and said he's had "amazing experiences with Kim, her mom, and the family."

On August 15, 2017, Kardashian West took to Instagram with swatches of her new powder contour kit. At the time, many of her fans — and even her makeup artist — teased the KKW Beauty founder about the splotchy lines she drew across her arm.

Then Star chimed on. In a now-deleted tweet, Star reportedly shared a screenshot of her Instagram story and wrote: "Umm... Kim what is going on with those new swatches?? Looks like chalk."

At first, Kardashian West seemed to take his comment in good fun, and even asked her fans on Instagram and Snapchat to stop sending Star hate for calling her out.

"I see that my fans are totally hating on someone like Jeffree Star for being honest about my struggle swatches, but because of his remarks, I'm learning from the best, like from Mario, how to swatch properly," Kardashian West said while laughing.

"And I see you being so petty, bringing up things in his past where he was negative, but he's also apologized for those things," she continued. "I get it's a serious deal if you say racial things, but I do believe in people changing, and people that apologize, I will give them the benefit of the doubt and accept that people change and move on."

"Hey guys, so I really wanted to apologize to you guys and my fans for defending a situation yesterday that I really didn't know enough about," Kardashian West said in a Snapchat and Instagram story. "I just feel a bit naive and I do wanna really apologize for me feeling like I had the right to say 'get over it' in a situation that involves racism."

"I just don't really feel like I have the right to speak on that, and I really, really, really am sorry," she continued.

Kardashian West went on to say that she originally defended Star because she's "always been about positivity" and doesn't want negative comments spread across her social-media platforms.

"So I really am sorry, and I just want to move forward and be positive," Kardashian West said. "And my last message is that just, I do believe that people are born to love and born with love and they're taught to hate, so I have always had hopes that people can change and learn to be better and do better, and learn to find that love again, so never give up hope."

"Every news and media outlet in the world has emailed and called my office all day asking me for a Kim. K quote," Star wrote at the time, according to Cosmopolitan. "Please f--- off. Talking about makeup has turned into a blood bath since yesterday."

He went on to say that there were "MORE IMPORTANT THINGS 2 WORRY ABOUT," including a "literal piece of s--- for a 'president' who is embarrassing our entire country." He added that he "#cantrelate."

"I get that people love drama and feed off of it, but attacking ME with hate and disgusting comments doesn't fix anything," he reportedly wrote. "You can't call me something that I'm not. It's getting old... Same b------- every time there's online drama. CHILL and worry about YOU."

"Who else is ready for this disgusting vile piece of s--- @POTUS to be #impeached?" Star continued. "The media wants to keep us all distracted by news headlines about me and Kim, but let's talk about how sad our country is right now."

Star then addressed his "haters," and urged them to "try fighting for something important."

"Because with how dark and depressing America is right now, I don't think I'm important," he wrote. "Stop wasting time on gossip and focus on reality. If you're upset about Jeffree Star and contour swatches and makeup drama, get the f--- out of my mentions. You're wasting your own time."

"The internet and media they really are trying it, so of course, I have to address it if I'm going to review this product," Star said at the start of his review.

Star first gave a timeline of events between himself and Kardashian West, and then repeatedly criticized social-media users and media outlets for bringing up racist comments he made in his past. He also urged his followers to take what they read in the media with "a grain of salt."

"There was so much media attention on this subject because of Kim, I got thrown under the bus a little bit," Star said. "Now, she did reach out to me — I do want to put that on record — because so many fake stories are out there."

"Kim reached out to me the next day, we spoke on the phone, we're all good," he continued. "Obviously I'm about to review her product because yes, she did still send me her makeup."

The vlogger gave Kardashian West's makeup a positive review, and said it was "Jeffree Star approved."

The makeup mogul first wrote a tweet about the price of Jenner's $360 brush set, writing: "Are the new @kyliecosmetics makeup brushes made out of animal hair? Is that why they're so expensive?? B---- I'M STILL DUMBFOUNDED!!!!"

He then followed up with another now-deleted tweet in which he accused Kylie Cosmetics of using the same packaging that his brand does for its concealer line.

"I gotta know ONE THING..." Star wrote. "With all the f------ money she's made, why did @kyliecosmetics use the SAME PACKAGING as my liquid lipsticks that have been out since 2014??? Invest and make something different maybe?"

He first described the Kylie Cosmetics brush case as looking "dinky" and feeling "very cheap." He also said he felt it could be purchased at Dollar Tree.

Star was a bit more forgiving when reviewing the actual brushes, though he still concluded his video by saying the set was "not Jeffree Star approved."

"For $360, plus tax and plus shipping, there is no way in hell I'm going to recommend to my audience that you guys buy basically a $400 brush set that you cannot touch or feel because of course, she is only an e-commerce brand," Star said. "So you are going to take the risk if you do wanna buy these of: are they gonna work for you or not?"

As reported by Seventeen, Star took to Twitter in January 2018 to ask why Jenner hadn't apologized for selling such expensive brushes. He's since deleted the tweet.

Later in February 2018, according to PopBuzz, he shared on Twitter that he had been removed from the Kylie Cosmetics PR list, meaning he'd no longer receive free products from the brand for him to review.

"Just for the record, I could care less about getting free products," Star wrote. "I buy anything I have ever wanted to review that you guys have told me about. I invest a lot into my channel and this is just pure comedy to me."

"I love when I speak the truth about a product, and then I get removed," he continued. "Hahaha these companies really be scared of the truth getting out to a huge audience."

Star concluded by saying he's in "a unique position" by reviewing makeup and also owning his own beauty brand. He also added that he'd continue to share his "100% honest opinions" in the future.

Before reviewing the Makeup by Mario x KKW Beauty collection on his YouTube channel, Star shared a shady message that referenced Jenner and Kylie Cosmetics.

"Now I know you shady b------ thought that just like Kylie, Kim took me off the PR list," Star said. He added that Kardashian West "can actually take some criticism" before winking at the camera.

Star later confirmed during the review that the products were sent to him by Kardashian West.

Star first said he was unimpressed with the brand's blush in the shade X-rated and would be throwing it "in the trash" because he felt it was too sheer. He then criticized Jenner's lipsticks, describing them as "a little drying."

"I just think that there's so many products being put out, it's not exciting anymore," Star said about Kylie Cosmetics. "It's kind of lackluster and I'm just kind of like over the brand at the moment. Maybe it's gonna re-excite me in the future, maybe not, but right now, kind of like over it, and kind of like meh."

In the midst of a cheating scandal between Khloe Kardashian, her on-again off-again partner Tristan Thompson, and Kylie's former friend Jordyn Woods, Star used social media to voice his opinion on the situation.

"Learn to co-parent on a healthy level and stop acting like your man isn't trash either," Star wrote in response to a tweet written by Khloe. "Thank you, now shut the f--- up. - The World."

He then claimed "the whole entire town" of Calabasas, California, knew Woods and Thompson had "been hooking up for at least a few months," and added that "the rest of the world is now being played by lies. Nothing new lol."

"I don't need to say 'allegedly' because I only speak facts," Star wrote on Twitter at the time.

He also shared a video about Khloe, Thompson, and Woods on Snapchat, saying "we gotta all as people stop giving a f--- about these idiots." He also called Thompson "a cheating, lying, piece of s---," and said "for some reason, Khloe don't really want to acknowledge that – you can't blame EVERYTHING on Jordyn, miss thing."

After Dictionary.com made a sarcastic tweet about Jenner's Forbes title, Star replied by saying he "declined the feature so they had to pick someone."

As Revelist pointed out at the time, Star's tweet didn't make perfect sense. Not only was Jenner named the youngest self-made billionaire as part of a feature on successful women in business, but there's also a big age difference between the two stars: Star is 35 years old, and Kylie is 23 years old.

On June 2, 2019, Star uploaded a video in which he reviewed the Kylie Skin line alongside Shane Dawson. At the start of his video, Star said he was both nervous and excited to try the line because people think "there's past tea," which Star acknowledged is true, before claiming the two "don't care about each other."

"There's no, like, real, like, animosity," Star said about his relationship with Jenner. "I just don't really review her stuff anymore on my channel."

As Star and Dawson began to review the products, Dawson said Kylie's vitamin C serum smelled "like dog bacon," while other products seemed "basic" to him. Star agreed and said his face "felt basic" after using Kylie Skin.

In early July 2019, TrendMood, a blog that tracks new makeup releases, announced on Instagram that Jenner would be releasing three new Kylie Skin products for the summer. In response to the post, Star commented: "Hahahahahha."

An Instagram user then mentioned that Star previously said he would no longer entertain beauty-community drama, and asked the YouTuber if he's tired of being involved.

"You should probably have a seat, because as a human being on this planet, I'm allowed to comment on anyone's releases," Star responded. "It's also my job."

Star added that Jenner's first skin-care drop "was a complete joke and was basically a money grab." He told the user to "relax before trying to come for" him, and added: "I'd rather save millions of people money than letting them be ripped off by a celebrity."

As Insider's Kat Tenbarge previously reported, 11-year-old Mason Disick — the son of Kourtney Kardashian and Scott Disick — said during an April 2020 TikTok livestream that Star is "like spoiled AF," or "as f---."

When entertainment journalist Nola Marianna Ojumo tweeted about the comment afterwards, Star tweeted and quickly deleted a message aimed at Mason, who was 10 at the time.

"I had $500 in my bank account six years ago," Star wrote. "Maybe he's confused with his own privilege versus mine being self-made, hopefully his father can educate him soon!"

Ava Louise — an "online provocateur" known for "stretching the truth for viral posts" — recently shared a TikTok video in which she claimed West has been "hooking up with a very famous" male beauty star for months, as Tenbarge previously reported.

There was no concrete evidence to back up the claims, though some people believed that Star and West both having homes near each other in California and Wyoming could be partial proof.

When the rumors first circulated, Star deleted a 2011 tweet about West written after one of his concerts. At the same time, fans of Star pointed out that the makeup mogul previously made a reference to having sex with West and other stars in his 2009 song "B----, Please."

YouTube drama star Daniel "Keemstar" Keem said via Twitter on Wednesday that he texted Star to ask about the theory, and also shared a screenshot of Star's response: "Hahaha I'm having the best time in Wyoming, come visit sometime!"

Star also shared two photos of himself on Instagram with the caption "I'm ready for Sunday Service ," referencing West's well-known Christian musical events. He then addressed fans who were looking for West in old photos he'd posted.

By Thursday, however, Star said in a YouTube video that he's "single" and "not sleeping with anyone." He also described the rumors about Kim and West getting divorced because of Star as the "dumbest s---" he's ever read.

"I like very tall men," Star said in his video. "Me and Kanye have never hung out and this whole thing is really funny."

Sources close to West and Kardashian West also told Insider that the rumors are false.

• Read more:
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