When it comes to Kim Kardashian, her success definitely hasn't always been built off the back of some things she's proud of and some other moments she wishes had gone differently. In fact, her career started "on her back" and as you'll read she definitely wasn't a fan of that!
Below we have 10 moments from the life of Kim Kardashian that we guarantee she wishes she could hit the rewind button on. Whether it's terrible fashion choices, decisions to get drunk off Grey Goose or the time she tried to be a musician, it's clear that she is not immune to falling flat on her face (...perhaps because of the liquor?)
Yet Kim is also incredibly successful and as you'll see from the other half of our list, there are plenty of photos of her that you are going to love seeing. It won't take long before you realize as you get through the list that she often parades around with little to no clothing on and leaves little to the imagination, which we're sure most guys will appreciate.
20 Doesn't (Within Reason) - Her Without Any Makeup On
When it comes to looking at the above two photos, you definitely may come away with two very different impressions. The one on the right clearly looks like an unprompted photo of Kim when she was trying to get somewhere in a hurry and clearly didn't intend to be photographed.
Sadly, that's exactly what happened and now that photo is never getting off the internet. The one on the right also features Kim, but it was a much more active choice. The photos were taken of her at the fashion show for Balenciaga.
"She got dressed, and we thought she looked so beautiful the way she was, just like that. She had a spray tan done, and her skin just looked so beautiful, and so we just decided, ‘Let’s go for it! No makeup.'", said her fashion consultant Mario Dedivanovic when asked about that day's outfit.
19 Does - Her Selfish Book
No matter what your stance on the Kardashian family is, it's definitely hard to argue that they have had some incredibly smart business ventures.
Kim is no exception to this and in 2015, she turned her ability to take selfies very well into her own book entitled Selfish which was financially successful enough to warrant an updated version released a year later.
There are several racy photos included throughout the book, including many that were taken for Kanye West's eyes only but we're sure you don't mind us giving you a sneak peak!
18 Doesn't - Project Runway Malfunction
The Kardashian family is definitely not immune to having their wardrobe choices leaving little to the imagination, and as you can imagine, that often means that wardrobe malfunctions can be a very real possibility.
When Kim was sitting down as a guest judge on Project Runway, she elected to wear the above outfit which shows off plenty of upper leg.
Unfortunately, it showed off more than she was expecting as paparazzi was quick to realize they could see her underwear and snapped several photos.
We're sure Kim was just glad she didn't decide to go commando!
17 Does - Her On Vacation In January
Kim Kardashian has several aspects of her life that we are sure you are immensely jealous of. One area that we are sure you are not jealous of, however, is the public spotlight that is always placed on these stars and the potential risk of their privacy and safety.
Kim got a first-hand experience of that this past year when she was robbed at gunpoint when staying in Paris. When talking about the experience on Keeping up with the Kardashians, she included more details such as that she was tied up and left in the bath.
Thankfully for the Kardashian clan, they have the money to take some pretty amazing vacations to unwind and recover. They did just that this past January jetting off to Costa Rica.
As you can see from our above photo, Kim definitely looks just as beautiful as ever.
16 Doesn't - Mrs. Doubtfire Dress
There are plenty of outfits that Kim Kardashian has worn that turned heads for all the right reasons, but that absolutely was not the case when she attended the Met Ball back in 2013.
It's hard to blame Kardashian after all the event is known for its unique outfits and she was pregnant...but then Robin Williams tweeted out a picture of him from Mrs. Doubtfire which looked just like her.
The designer of the dress Riccardo Tisci defended his work, saying "I think she looked amazing. She was the most beautiful pregnant woman I dressed in my career."
15 Does - Her Shoot For Hef's Mag
Kim Kardashian has done plenty of racy things in her career, but one of the biggest definitely came when she accepted a call from Hugh Hefner and decided to strip down for Playboy in December 2007.
While the magazine ended up being incredibly successful when Kim was asked about the experience, she replied,
"I’m sorry I did Playboy. I was uncomfortable," and added that she felt immense pressure coming from Caitlyn to pose for the magazine.
While it's clear that Kim is comfortable nude, that definitely wasn't the case on that day!
Kim did, however, go on to say, "You always see the typical skinny models and I'm not that and I'm proud not to be that," which is enough for it to land on the positive side of our list.
14 Doesn't - Her Tape With Ray J.
There are always going to be things in your life that you regret, but it can be much harder to forget about it if it becomes public knowledge.
For Kim, she admitted one of her biggest regrets was her sex tape that shot her to fame,
"If I do have one regret in life, that's it. Maybe that's how some people heard about me but I didn't launch my career off of that. That was 12 years ago, no 13 years ago now, so I just try to move on and put it in the past because I think that everyone in life does things they're not proud of but you can't sit and dwell on them forever."
We're glad she has a positive attitude towards not dwelling on it, but we're sure she wishes she had become famous some other way!
13 Does - Her Paper Photoshoot
Kim Kardashian definitely set out to get public attention back in 2014 when she posed for Paper magazine. Not only did she strip down, but anytime you see that much oil on someone, you're definitely going to be garnering some serious attention.
But when it came to stripping off her clothes, editorial director Mickey Boardman said it was all her idea,
"It was her idea to take off her clothes and show more than her butt. We didn't say, 'Let's do a cover with your butt hanging out.' She said she was willing to take her clothes off, and one thing led to another...history in the making."
The costume was funnily parodied by Kelly Ripa back in 2015 for her Halloween special.
12 Doesn't - North West Falls Down
When it comes to being a celebrity parent, you need to understand (even if it's not fair) that the world is always going to feel comfortable chiming in with their own opinion on how you are doing as a parent.
Kim was on the receiving end of some serious negativity back in April 2016 after North West took a tumble to the ground while walking into the Los Angeles Museum of Art.
She was unaware of the incident, having instead chosen to focus on whatever was going on, on her phone. Thankfully Kourtney was there to help pick up the slack, but we're sure Kim isn't going to forget these photos anytime soon, even if she'd rather they don't exist.
11 Does - In Yoga Pants
Let's be honest guys, you wouldn't be alone if you love seeing Kim Kardashian (or you know, tons of celebrities) hanging out in yoga pants.
Thankfully for you, in a past interview, Kardashian admitted "There's nothing better than getting up and going right to the gym," you can just hope that she chooses to go to gyms that are out in public!
Kim not only loves working out, but she has even released several workout DVDs including one titled Fit in Your Jeans by Friday.
Kardashian also has a partnership with QuickTrim which is a diet product.
10 Doesn't - Drunk On Grey Goose
Kim Kardashian definitely has enough money that she could go out and get drunk on a regular basis, but you can imagine her two kids keep her a little bit more grounded.
In fact, when Khloe was asked about which of her sisters don't drink she singled out Kim saying,
"Kimberly does not drink alcohol whatsoever. Pregnant or not, she's just never been into it."
Perhaps Kim had too many nights of her slamming back the Grey Goose like in the above photo and decided to swear off it!
9 Does - Her Losing The Baby Weight
Kim Kardashian is no stranger to getting her photo taken and you better believe that didn't stop when she got pregnant with her son Saint back in 2015.
When talking about her body and how she felt after giving birth, Kardashian admitted,
“There was a moment after [son Saint was born last December] when my body was mush. I felt like Gumby. There was definitely a moment when I looked in the mirror and I was like, ‘I am never going to be the same.’"
But it was clear by the time the VMAs rolled around in 2016 that Kim had clearly been able to lose the baby weight.
8 Doesn't - Her Abusive Marriage To Damon Thomas
Kim Kardashian may be known for her marriage to Kris Humphries for a brief time and more recently Kanye West, but her most abusive relationship definitely happened when she was younger.
Kim got married to Damon Thomas, a music producer, when she was only 19 years old and the relationship was full of abuse.
"Damon told me not to leave the house unless I first told him when and where I was going. Sometimes, Damon would not allow me to leave," and that on several occasions he would punch her repeatedly or throw her across the room.
She also stated that the abuse happened after their marriage was dissolved, detailing one incident in which she said,
"He held me up against the wall with his hands around my neck and threatened to choke me. He then took one hand and punched the wall right next to my head."
Kim said that while she wanted to call the police, Damon had emotionally and physically beaten her down to the point where she no longer felt safe.
7 Does - Her Halloween Costume As Jasmine
There aren't many movies that can instil a level of nostalgia in people quite like Aladdin. Not only does it star the incredible Robin Williams, but it also features one of the most beautiful Disney princesses in Jasmine.
So naturally, when Kim Kardashian decided to go as Jasmine for Halloween it was going to garner a pretty positive reaction!
In fact, Kardashian re-created the look (which she first wore in 2009) earlier this year after her children became obsessed with the movie.
Kim's sibling Rob opened up about the costume saying, "She couldn't disappoint North once [North] saw she had a Princess Jasmine costume from back in the day.”
6 Doesn't - Anything Related To "Jam (Turn It Up)"
Kim Kardashian does several things well, but one thing that she definitely does not is sing. But kudos to her (we suppose) for trying and back in 2011 when she released the song "Jam (Turn it Up)".
The song definitely flopped and in a past interview, Kardashian admitted that she wished she never did it,
"But if there’s one thing in life that I wish I didn’t do ... I don’t like it when people kind of dabble into things they shouldn’t be. And that I don’t think I should have. Like, what gave me the right to think I could be a singer? Like, I don’t have a good voice.”
If there is one positive, any profits that the song did make were donated to a cancer organization.
5 Does - When She Had Nothing to Wear
Kim Kardashian has had several eye-catching Instagram photos over the years, but none bigger than the time she elected to strip off all of her clothes and humorously captioned the photo on Twitter with "When you're like I have nothing to wear LOL".
After several people came out and criticized Kardashian for showing off that much skin, she fought back saying,
"I don't do drugs, I hardly drink, I've never committed a crime – and yet I'm a bad role model for being proud of my body?"
When you consider she did this again, except this time also bringing in one of the biggest models in the world, you can imagine she had no regrets!
4 Doesn't - The Old Navy Commercial Drama
Kim Kardashian is no stranger to controversy but back in 2011, it was Old Navy that she was trying to get in hot water. The company released a commercial that featured the actress/model Melissa Molinaro and people online were quick to point out the resemblance to Kim.
In fact, the resemblance (which you can judge for yourself) was so significant that Kim sued the company for $20 million and sought to make sure that Molinaro never appears in the commercials again.
It definitely wasn't the best look for either side and in 2012 the lawsuit was settled out of court. We're sure that Kim wouldn't mind you just forgetting about the whole thing, which we're sure you would have done a lot sooner had she not made a huge deal out of it.
3 Does - Her Instagram Photo With Emily
Are you really going to be hating on us if this list includes two photos of Kim Kardashian deciding to forget clothes before posting on Instagram?
Above you read about the time she did it alone, but as you can see from the above photo she stripped down shortly after again this time also including Emily Ratajkowski.
Ratajkowski who had publicly supported Kardashian from the start shared the photo along with the caption
"We are more than just our bodies, but that doesn't mean we have to be shamed for them or our sexuality. #liberated."
2 Doesn't - Marriage To Humphries
Kim Kardashian may appear to be happily married to Kanye West, but you can imagine there weren't many happy days with her second husband Kris Humphries.
The two got married back in August 2011 after starting their relationship back in October of 2010 and after 72 days of marriage, the two filed for divorce.
Perhaps fittingly, Kim started pursuing Kanye very shortly after; including giving birth to Kanye's kid 12 days after her divorce with Humphries was finalized.
1 Does - Her Upcoming Cameo On Ocean's 8
Kim K. may be not be known for her acting ability (trust us), but she is going to try and change that perception with her upcoming cameo in Ocean's 8. While it isn't clear as to how big of a role that Kim will be playing, it's certainly got to be an exciting opportunity for her and one that we're sure she is more than happy to talk about.
Especially when you consider the wardrobe she is in doesn't leave a ton to the imagination.
Kardashian was perhaps a natural selection for the movie as it is centered around a jewel heist that targeted celebrities; something she has just a bit of experience in!
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