Kim Kardashian's Best Career Moves (And 7 Of Her Most Embarrassing)

Viewers of "Keeping Up with the Kardashians" and the family's new Hulu show have had an inside look at Kim Kardashian's career from the very beginning. From her early days as an influencer and paparazzi favorite to her decision to become a business founder and owner, Kardashian has always maintained a direct line of communication with her fans. With more than 353 million Instagram followers, Kardashian remains one of the most famous people in the world, but she was far from an overnight success.

In September 2022, Interview asked Kardashian what her life would be like if she wasn't famous. "I'm going to dinner with my sisters tonight, so I'd probably do that anyway. I think I'd always be working out," the reality television star revealed. "None of that has really changed. Me and my sisters would always work out together. I would be a mom. I'd still want to work, though. I'd probably have a big vintage resale business or something." Of course, this alternate timeline is worlds away from Kardashian's current reality, in which her success only seems to keep growing. Here, we examine the shrewd career moves that helped Kim Kardashian build her business empire, as well as some of the more embarrassing choices she made along the way.

"Keeping Up with the Kardashians" first launched on E! in October 2007, and quickly became a huge reality TV hit. In March of the same year, a sex tape featuring Kim Kardashian had been released by Vivid Entertainment, giving the star a level of notoriety she apparently didn't want at the time. According to Page Six, Kardashian had filmed the footage in 2002 while on vacation in Cabo with her then-boyfriend, Ray J. Per the publication, Kardashian didn't want the tape, aptly titled "Kim Kardashian Superstar," released and she sued Vivid Entertainment to try and stop production. In an interview with Page Six, the founder of Vivid Entertainment, Steven Hirsch, said, "I know people have speculated on [whether she planned the release of tape from the beginning], but the facts are the facts. ... The persistent rumors about Kris Jenner, Kardashian's mother, being involved in selling the tape are] such nonsense."

And there has been a lot of speculation about whether or not the reality star was involved; Ray J has even claimed Jenner and Kardashian played a major role its release. However, the former CEO of E! Networks, Ted Harbert, told The Hollywood Reporter in 2017, "Ad sales departments don't tend to jump up and down about shows that feature people that have been in sex tapes." Whatever the case, Kardashian's appearance in a sex tape could have hindered her success, if anything, but instead, it was only the beginning of what has been an unparalleled career. 

When Kim Kardashian announced that she was releasing a mobile game called "Kim Kardashian: Hollywood," nobody could've predicted how successful it would become. As reported by The New York Times, when the game was released in June 2014, it made a whopping $1.6 million in revenue in just five days on the market. Inspired by Kardashian herself, the game allows players to invent their own wannabe celebrities, and then attempt to climb the ladder of success, much like the reality TV icon did. Per The New York Times, the company responsible for designing the game, Glu Mobile, approached Kardashian about partnering on a potential game in 2013, believing that she was the perfect fit for their brand.

While Glu Mobile hasn't revealed the exact details of its deal with Kardashian, it's likely that reality star banked some sizable cash thanks to the game. According to Forbes, insider estimates suggested that she likely took home somewhere between 30% and 45% of the game's profits, which would equate to millions each year. Niccolo de Masi, the chief executive of Glu Mobile, the company behind the super popular game, told The New York Times, "There will be a lot of opportunities to work with Kim to expand her brand and awareness ... Ultimately, she's just getting started." Basically, what started as a simple mobile game quickly became a hugely important career move for Kardashian.

Following in the footsteps of sister Kylie Jenner's Kylie Cosmetics, Kim Kardashian founded her own makeup line called KKW Beauty. She launched her brand in 2017 with her famous contour kit, which was available in several shades, and quickly sold out. She added perfume to her roster later that year with KKW Fragrances, selling approximately $14 million worth of products in less than a week. She also expanded her beauty line to include everything from mascara to eyeshadow palettes to concealer.

Proving that there's a lot of money to be made from celebrity makeup brands, Coty purchased a 51% stake in Kylie Cosmetics in 2019 for $600 million. In 2020, Kardashian followed suit and sold a 20% stake in KKW Beauty to the very same company that had made a deal with her younger sister. Per Forbes, Coty paid $200 million for the 20% stake in Kardashian's company, meaning that her cosmetics brand was valued at a cool billion. In 2021, Kardashian announced her decision to discontinue KKW Beauty, and in 2022 she revealed her new skincare line, SKKN by Kim. There's money to be made in the beauty business, and Kardashian has embraced her influence in the makeup and skincare space to great acclaim.

In a career move that surprised the world, Kim Kardashian announced that she was pursuing a law degree, following in the footsteps of her father, Robert Kardashian, who famously represented O.J. Simpson. In a May 2019 Vogue profile, it was revealed that Kim was logging 18 hours of supervised study every week in an attempt to become a lawyer. "First year of law school ... you have to cover three subjects: criminal law, torts, and contracts," she told Vogue. "To me, torts is the most confusing, contracts the most boring, and crim law I can do in my sleep. Took my first test, I got a 100. Super easy for me." It was also revealed that the KKW Fragrance founder would need to complete the "baby bar" in order to continue with her studies.

In December 2021, Kim took to Twitter to reveal that she had passed the "baby bar," writing, "Looking in the mirror, I am really proud of the woman looking back today in the reflection." She also shared, "I failed this exam 3 times in 2 years, but I got back up each time and studied harder and tried again until I did it!!!" The reality star has already used her law knowledge to petition for prison reform and fought for the release of several people she suggests were wrongly imprisoned. Plus, she personally lobbied then-president Donald Trump for the release of Alice Marie Johnson, which was successful.

Having successfully launched everything from mobile games to fragrance lines, Kim Kardashian turned her expertise to shapewear. In September 2019, Kardashian dropped her first line for Skims, a shapewear brand inspired by her own experience with red carpet and everyday dressing. According to TMZ, Kardashian's first release was incredibly successful, with the icon reportedly raking in approximately $2 million within a matter of minutes.

In April 2021, The New York Times reported that Skims was valued at approximately $1.6 billion, after just two years and following a fresh round of investment funding. After initially selling shapewear and underwear, Skims quickly diversified and began launching sleepwear, comfy outfits to wear at home during the pandemic, swimwear, and activewear. Discussing the brand's success, Kardashian told The New York Times, "We're your basics go-to ... we're still able to keep that shapewear core." As for whether or not she'd ever sell Skims, like she did with her beauty brand, Kardashian told the publication, "I think I'm open to the conversation, for sure ... I would never want to give up my process. I would hope that whoever we partner with in a sale one day would believe in that, too."

Kardashian's shrewd business sense led to Forbes declaring her a billionaire in April 2021, thanks to both her success with Skims, and her KKW Beauty deal with Coty.

It's no secret that Kim Kardashian is a savvy businessperson who has been building a billion-dollar empire for years. One aspect of her life that she cleverly monetized early on was her social media presence. In May 2019, Insider noted that Kardashian had filed a lawsuit against the fashion company Missguided, and in doing so, had revealed how much money she commands for Instagram endorsements. Per the publication, Kardashian revealed in an affidavit that she often earned as much as $300,000 to $500,000 for simply promoting a brand or product on her social media accounts. It was also noted that Kardashian also entered into multimillion dollar deals with companies that wanted to work with her on a longer basis. Basically, she's making bank on Instagram.

Discussing her decision to file a lawsuit against Missguided for allegedly using her persona and likeness without her consent, Kardashian said in an affidavit, "Because a significant portion of my business involves the licensing of my name, trademarks, and images, I work very hard to ensure that my brand means something to my fans and to the public, who view the use of my name as the stamp of approval by me." Just being Kim Kardashian is worth a hell of a lot of money, it seems.

As one of the world's most recognizable stars, Kim Kardashian's image is understandably worth a lot of money. In a savvy career move, the reality TV veteran decided to create a book of selfies, including previously unseen photos of the star, taken throughout her entire life. "Selfish" caused quite a stir when it was published in May 2015, and all eyes were on the Skims creator as she promoted the self-referential tome. In an interview with E! News, Kardashian revealed how she chose the selection of photographs, saying, "There was a lot I had to edit out of there. I decided not to go too nude, because I didn't wanna go too crazy." 

Some initial reports suggested that "Selfish" was a failure, but Kardashian's publisher was quick to put those rumors to rest. In a statement to Us Weekly, Pam Sommers, the executive director of publicity at Rizzoli, said, "The book is, in fact, a significant success story as a benchmark of the phenomenon of self-portrait in the digital age." Seemingly dispelling the idea that sales of the book were disappointing, the Daily Mail reported that limited edition copies of "Selfish," which had been signed by the icon, sold out in mere minutes. Further proving that her selfies were still in demand, Kardashian released an expanded edition of the book in 2016.

When Kim Kardashian hosted "Saturday Night Live" in October 2021, multiple reviewers declared their genuine surprise that she actually did a good job. In her hilarious opening monologue, Kardashian told the audience, "I know, I'm surprised to see me here too." She also quipped, "I'm so much more than that reference photo my sisters showed their plastic surgeons." Kardashian went on to make jokes about her father representing O.J. Simpson, her divorce from Kanye West, and her failed movie career. 

A skit inspired by "The Bachelorette" saw Kim romance Amy Schumer, while her impression of sister Kourtney Kardashian was ridiculously accurate. But the most memorable sketch saw Kardashian and Pete Davidson portray Jasmine and Aladdin, and kiss onscreen. As they started dating after Kardashian's appearance on "SNL," the sketch gained even more significance. During an April 2022 appearance on Dear Media's "Not Skinny but Not Fat" podcast, Kardashian discussed kissing Davidson for the first time. "[It] was a stage kiss, but it was, like, still like a little zing, you know? It wasn't anything like a super-crazy feeling," she revealed. "I was just like, 'Hmm.'" Basically, "Saturday Night Live" was a great career move as it started an international conversation about Kardashian, thanks to both her comedic abilities and her sizzling connection with Davidson.

Throughout her career, Kris Jenner's second eldest has worked hard to be taken seriously, and that most definitely applies when it comes to fashion. Kim Kardashian's style has continually evolved throughout her life, but in recent years, a number of high-end brands have started collaborating with the reality TV star on a regular basis. In July 2022, Kardashian solidified herself as a respected fashionista when she walked the runway for Balenciaga at Paris Couture Week. As noted by Variety, Kardashian's status as a fashion model was further elevated due to the caliber of celebrities walking in the show, which included singer Dua Lipa, actor Nicole Kidman, supermodel Naomi Campbell, and former "Selling Sunset" cast member Christine Quinn.

As well as hitting the runway, Kardashian was spotted attending multiple fashion shows for some of the world's most famous designers. Her style caught everyone's attention, with the star wearing jaw-dropping looks by Jean Paul Gaultier and Balenciaga. Kardashian also coordinated with her eldest daughter, North West, while attending shows, and the pair were even spotted sitting Front Row with Vogue editor Anna Wintour. It took some time, but Kardashian slowly but surely incorporated fashion into her career trajectory with huge success.

Kim Kardashian's early attempts at acting didn't exactly go as planned (more on that later), but she might be about to turn that all around. In an unexpected career move, Kardashian has decided to return to acting, in a popular TV series, no less. In April 2023, it was revealed that Kardashian would be joining Emma Roberts in Season 12 of "American Horror Story." The anthology series has been known to cast unexpected celebrities in surprising roles, with everyone from Lady Gaga to Adam Levine to Joan Collins making an appearance. As a result, the announcement that Kardashian is joining the cast isn't completely out of the ordinary, but it certainly marks an ambitious career move for the star.

Series co-creator Ryan Murphy told The Hollywood Reporter in a statement, "Kim is among the biggest and brightest television stars in the world and we are thrilled to welcome her to the 'AHS' family." He continued, "Emma [Roberts] and I are excited about collaborating with this true force in the culture. Halley Feiffer has written a fun, stylish and ultimately terrifying role especially for Kim, and this season is ambitious and unlike anything we have ever done." The new season of "American Horror Story" can't come soon enough for fans of Kardashian's career.

Kim Kardashian has had an incomparable career, but she also had some humble beginnings she probably wishes we'd forget about. While there are conflicting reports regarding what Kardashian actually did when she worked for heiress and DJ Paris Hilton, an episode of "The Simple Life" showed the Skims creator organizing Hilton's closet. 

"I would work with Paris, and I would love to organize and clean out their closets and get rid of all their stuff and sell it on eBay and then shop for them, shop for her. That was my job," she said on a 2017 episode of "Watch What Happens Live." "I loved it. But people will say 'assistant.' They always have it wrong." So, according to Kardashian, she wasn't actually Paris Hilton's assistant, but she was someone who sold Paris Hilton's old clothes. Of course, working for and hanging out with a star like Hilton isn't embarrassing, but there were a few scenes on the show that suggested the gig could get a bit cringeworthy; Daily Beast went so far as to call Kardashian the socialite's "punching bag."

Kardashian's connection to Hilton undoubtedly helped her career in the long run, especially as the pair was often photographed together by the paparazzi. However, the whole "closet organizing" situation is a slightly embarrassing chapter in Kardashian's rise to fame, and seems worlds away from the life and career she's built since then.

Endorsement deals can be an incredibly lucrative way for celebrities to make money. However, there are probably some endorsements that Kim Kardashian isn't eager to revisit, such as the time she opened a toilet for Charmin. Yes, you read that correctly. In November 2010, Kardashian posed up a storm outside the Charmin Restrooms in Times Square, even cuddling up to the Charmin bear mascots. Dressed in a demure gray dress and black heels, Kardashian was responsible for the ribbon-cutting ceremony that opened the Charmin toilet facilities to the public. Said appearance wasn't exactly the Met Gala red carpet; as the Daily Mail put it at the time, this particular endorsement "plumbs new depths."

Per PR Newswire, Kardashian said at the event, "With my recent transition to New York, I've been checking out all the gifts the City has to offer visitors and New Yorkers alike." She continued, "During the holiday shopping season, I'm happy to join Charmin as they give the gift of the Restrooms near Times Square." As for why Kardashian decided to throw her name behind the toilet paper brand, the simple answer is likely money. But it's hard to wonder if the star looks back on her toilet-opening days with a little embarrassment now that she's a billionaire.

Reality TV may have made Kim Kardashian famous, but that doesn't mean that every show she's appeared on has helped her success. In fact, Kardashian's 2008 appearance on the seventh season of "Dancing with the Stars" was widely derided, with her dance moves and lack of coordination regularly criticized on the show. Unfortunately, Kardashian was eliminated early on in the season, despite being paired with Season 6 winner Mark Ballas.

For her part, Kardashian was forthcoming about her lack of experience in the dancing arena. In a MySpace blog post, the KKW Beauty founder discussed her preparation for appearing on the competition show, writing, "I've never taken a dance class in my life ... the second thing I thought of was, could I really do this?" She also opened up about her progress as a dancer, writing, "Of course I have my moments where I lose my balance or I lose my place, and some days are better than others." Sadly, dancing just simply wasn't Kardashian's forte, and she was the third contestant voted off that season, bowing out in Week 2. Well, you can't be good at everything, right?

In March 2011, Kim Kardashian surprised the world by announcing that she'd recorded a single called "Jam (Turn It Up)," and that she'd be donating a portion of any money made by the song to St. Jude Children's Research Hospital. In a blog post, Kardashian explained, "This was definitely something that was out of my comfort zone, but I'm so glad that I met with The-Dream and that we worked on this project together. It was really an amazing experience recording in the studio and filming the music video." Unfortunately, the world wasn't ready for Kim Kardashian's pop star moment, and negative reviews flooded in.

As for how she feels about the song now, Kardashian has been open about her musical ability... or lack thereof. When she went on "Watch What Happens Live" in August 2014, Kardashian made it clear she doesn't stand by the single. "I don't like it when people kind of dabble into things they shouldn't be," she said (via HuffPost). "Like, what gave me the right to think I could be a singer? Like, I don't have a good voice." 

While the release of her first and ever song might have been a little embarrassing, "Jam (Turn It Up)" lives on. In October 2021, Kardashian revealed in an Instagram Story that her children had been playing her pop song on repeat in celebration of her 41st birthday. Maybe it was a bop after all?

If you thought that opening a toilet in Times Square was a little awkward, just wait until you hear about Kim Kardashian's questionable endorsement deals. Per the Daily News, Kim and her sisters faced a class action lawsuit for promoting QuickTrim, a supposed weight loss product, the main ingredient of which was caffeine according to the FDA. QuickTrim reportedly generated $45 million in sales thanks to Kim, Khloé, and Kourtney Kardashian, but shoppers were allegedly less-than-happy with the famous family for slapping their names on the product.

In May 2018, Kim came under fire once again for promoting a seemingly sketchy weight loss product, this time on Instagram. As reported by ELLE U.K., Kim posted a photo of herself licking a lollipop by Flat Tummy Co., writing, "They're Appetite Suppressant Lollipops and they're literally unreal." The overall reaction to the endorsement was generally negative, with actor Jameela Jamil tweeting her opposition to the promotion.

While the weight loss product endorsements are undoubtedly the most cringeworthy, Kim has put her name and face to everything from nail polish to footwear to watches and salads. As a huge part of her career was once based upon endorsing other people's products, it's likely that some of those choices would be at least a little bit embarrassing.

In March 2022, Variety interviewed the Kardashian clan about their new Hulu show "The Kardashians," and the secret to the longevity of their success. In a video clip shared by Variety, Kim Kardashian quickly angered fans when she announced, "I have the best advice for women in business. Get your f***ing a** up and work." Without a sense of irony or acknowledgement of familial and financial privilege, Kardashian literally told people all over the world that they simply needed to try harder and give their work ethic a tune up. She continued, "It seems like nobody wants to work these days." Understandably, the pushback against these comments was swift and brutal.

Unsurprisingly, the media mogul then had to walk her words back a bit. During an appearance on "Good Morning America," she stated, "It was taken out of context, but I'm really sorry if it was received that way." She also said during her apology on the show, "It wasn't a blanket statement towards women or to feel like I don't respect the work or think that they don't work hard. I know that they do." Unfortunately for Kardashian, the damage had already been done, with even "Good Morning America" noting that the reality star's comments failed to address the employment crisis caused by the pandemic, and the fact that women of color and mothers had been disproportionately affected by career changes caused by COVID-19.

Kim Kardashian may finally be returning to acting with her role in "American Horror Story," but her previous attempts to be a thespian haven't always gone down that well. For instance, in 2014 she won the Razzie award for Worst Supporting Actress for her performance in Tyler Perry's "Temptation: Confessions of a Marriage Counselor." Critics universally panned Kardashian's attempts to graduate to bonafide film star, and her Razzie seemed to suggest that acting might not be the right career path for the multi-hyphenate. Basically, the media circus surrounding her performance in the Tyler Perry film had to be a little embarrassing to handle at the time.

Prior to the "Temptation" debacle, Kardashian had been building a portfolio of acting roles, which included a part in 2008's "Disaster Movie," and appearances in TV shows such as "How I Met Your Mother," "CSI: NY," "30 Rock," and "Drop Dead Diva." Despite receiving so much criticism for her acting in the past, Kardashian's decision to overcome the embarrassment to star in "American Horror Story" is pretty brave and something to be applauded. Whether her career moves have been good or bad, Kardashian has built an empire, and it doesn't seem as though she finished just yet.