Demi Moore has made some controversial decisions

Demi Moore has made a lot of the right moves throughout her acting career, which is why she became one of Hollywood's biggest stars in the '80s and '90s. But she's also made her fair share of questionable choices that have left some fans scratching their heads and others completely offended. 

However, even fierce criticism hasn't stopped Moore from doing what she wants. She explained her perspective on living for herself instead of others during a 1996 chat with Interview magazine, saying, "In the end ... the only thing that you can have on your side is time. The only way to gain time is by living it. And if I live expending my energy worrying about other people's perceptions, then I'm missing my moment." Moore backed up that mindset during an interview with Harper's Bazaar in 2012, calling being present "freedom."

While that sort of freedom seems like something to strive for, it's also perhaps what has led Moore to opt for iffy, risky, and at times downright destructive behavior. Although the star isn't likely to stop shocking us anytime soon with her sometimes bold, brave, and arguably cringeworthy ways, here are some of the most controversial decisions that Demi Moore has ever made.

Demi Moore's first marriage was problematic before they even said 'I do'

In 1981, when Demi Moore (who went by Demi Gene Guynes at the time) was just 18 years old, she married musician Freddy Moore — yes, that's how she got her famous last name. Unfortunately, their union was dubious right from the start due to the fact that Freddy had just gone through a divorce and was also 12 years older than his new wife. However, what the public saw — and judged — was just the tip of the iceberg when it came to the scandalous situation that played out behind the scenes. 

Demi admitted in her 2019 memoir, Inside Out (via People), that she cheated on Freddy just before their wedding. "The night before we got married, instead of working on my vows, I was calling a guy I'd met on a movie set," she confessed. "I snuck out of my own bachelorette party and went to his apartment." 

"Why did I do that?" Demi continued. "Why didn't I go and see the man I was committing to spend the rest of my life with to express my doubts? Because I couldn't face the fact that I was getting married to distract myself from grieving the death of my father. Because I felt there was no room to question what I'd already put in motion." Explaining the underlying motivation for her actions, she wrote, "I couldn't get out of the marriage, but I could sabotage it."

She made Jon Cryer's private life public with a shocking claim

In Demi Moore's Inside Out memoir, she not only went public about her own private life, but also shared details about former Two and a Half Men star Jon Cryer's personal past, which seemed to come as a surprise to the actor. Moore and Cryer worked together on 1984's No Small Affair, which was when Moore claimed she took her former co-star's virginity.

"I played a young nightclub singer, and Jon Cryer played the nineteen-year-old photographer who falls in love with her, in his first movie role," she wrote in her memoir (via E! News). "Jon fell for me in real life, too, and lost his virginity to me while we were making that movie." She continued by stating that, from her perspective, she "stole what could have been such an important and beautiful moment from him."

However, Cryer remembered things a little differently when it came to their past. While he didn't deny that he had slept with Moore, he did take to Twitter to refute the claim that he was a virgin at the time: "Well, the good thing about this is she doesn't have to feel bad about it anymore, because while I'm sure she was totally justified making that assumption based on my ... skill level (and the stunned look on my face at the time), I had actually lost my virginity in high school."

That time a naked and pregnant Moore appeared on a magazine cover

In 1991, Demi Moore posed for photographer Annie Leibovitz while seven months pregnant with her second child with then-husband Bruce Willis. Since Moore was naked in the image, which ended up on the cover of Vanity Fair, it caused a quite a stir. A writer for the Chicago Tribune, for example, was "appalled by the whole extraordinary exhibitionist business," describing the photo as the "OB-GYN examining room ... cover of Demi strategically cradling her amplified elsewheres."

While the image certainly piqued the public's interest, it initially wasn't meant to be seen by others at all. Vanity Fair's editor Tina Brown told CNBC that she'd "been looking for a cover that would sort of turn the mood from the '80s right into the new '90s feeling of a slightly fresher era." At this, Leibovitz revealed to her, "There is this other picture that I took, but I really did it for just Demi and Bruce Willis." That private photo made it onto the cover of the magazine and was so seemingly scandalous that Walmart wouldn't sell it. Despite the strong reaction — or perhaps because of it — Time magazine included it among their list of 100 Most Influential Images of All Time.

As for Moore, she told Interview, "I didn't realize that it would spark that degree of controversy because I don't have that kind of thinking ... Believe me, I never set out to make any big statement."

Demi Moore was shamed for her children's names

It's not unusual these days for famous parents to give their children unique (and even somewhat strange) names, but Demi Moore and Bruce Willis certainly had people judging their choices back in the day when they opted to name their daughters Rumer Willis, Scout Willis, and Tallulah Willis.

They may not be the most common names, but each of their daughter's was given a moniker that has meaning. Rumer was named after the revered British novelist Rumer Godden, Scout's name was inspired by the main character in Harper Lee's classic book To Kill a Mockingbird, while Tallulah's name honored the late Hollywood and Broadway star Tallulah Bankhead, who was also a supporter of civil rights.

However, the fact that each name held a special significance didn't shield them from harsh critique. In fact, the Chicago Tribune published a full piece shaming the famous parents over the matter following Scout's birth in 1991: "I'm sure Demi and Bruce had nothing but the best in mind for their little lovely, but far too many parents, I fear, self-indulgently inflict ridiculous sounding monickers on their offspring just to enhance their own self image." Despite that, the writer was willing to concede that when it came to Scout's name, perhaps "we can be thankful that Demi and Bruce decided against 'Mockingbird,' though maybe not."

She risked 'overexposure' in Striptease

Although Demi Moore's personal life has caused controversy over the years, her career hasn't escaped criticism, especially since she hasn't shied away from risky roles. That's a fact that can't be denied by anyone who's seen her 1996 film, Striptease, in which she plays a single mother who turns to stripping.

Due to the body-baring role, Entertainment Weekly posed the question: "Does Demi Moore risk overexposure?" Noting that "the star has managed to enrage film critics" with this particular movie, the media outlet added, "Typical was one rant by Gene Siskel, who asked: 'What's next? Demi has a baby on camera?'"

The brutal criticism was backed up by the fact that the film and its star were given a slew of unfortunate Razzie Award honors, including worst actress and worst picture. Critics may not have loved the film, but Moore claimed it was a transformative experience. "I found myself in a film [Striptease] that has to do with the body, both the external and internal issues of it. And by moving through it, it changed me," she told Interview. "It changed my perception of me ... of my body and of my acceptance of myself."

Her G.I. Jane role was just as risky for a different reason

In 1997, Demi Moore appeared in director Ridley Scott's G.I. Jane as the first woman to tackle the U.S. Navy Special Warfare Group training — which was obviously an interesting pivot when it came to roles. Unfortunately for the actress, the gig also earned her another worst actress Razzie Award, and caused just as much critical chatter as her earlier scandal-sparking work.

Not only were fans shocked by the fact that Moore had shaved her head down to a buzzcut to portray the hardcore character, but there was also a backlash regarding the accuracy — or, more specifically, the supposed lack of accuracy — when it came to the nature of the military. Retired SEAL Tom Hawkins told The Baltimore Sun, "If I were an instructor at B.U.D.S. [basic underwater demolition SEALS], I'd be very angry with this movie." He added, "The way they present training is bloody way off the mark." 

Moore, on the other hand, gave Interview a very different reason for the response to her work in general. "I don't know if I personally instill a fear in people, but I think that there are things that I have been involved in that perhaps stir up their own personal fears," she said, adding, "I have no control over people thinking that way, and I always feel that those kinds of things are attempts to make me less."

Demi Moore was associated with the questionable cosmetic knee surgery trend

The pressure for Hollywood actresses to be picture perfect is undeniably intense, which is why Demi Moore was once rumored to have had a knee-lift to deal with saggy skin (a.k.a. knee wrinkles or "kninkles").

"Those eyes! Those lips! That cleavage! But those knees? You know Hollywood has jumped the shark on its addiction to perfection when the focus has shifted from erogenous zones to a humble utilitarian joint," The Hollywood Reporter wrote about the trend. "But when it comes to the town's actresses, power execs and wealthy wives, what else is there left to fix? Telltale signs of aging competently have been eradicated (sometimes overly so) in the marquee body parts, so science and vanity have moved on to less fetishized, subtler but still age-betraying areas: the hands, neck and, yes, knees." 

However, despite being the famous figure that brought the procedure into the news, Moore denied that she'd had any work done in 2009. "I don't like the idea of having an operation to hold up the aging process, it's a way to combat your neurosis. The scalpel won't make you happy," she told Marie Claire. "That said, the day when I start crying when I look at myself in the mirror might be the day when I'm less adamant about not having it done. For the moment I prefer to be a beautiful woman of my age than try desperately to look thirty."

Her iffy marriage to the much younger Ashton Kutcher

Although Demi Moore's career-related controversies had taken center stage during the '90s, she apparently wasn't finished shocking fans when it comes to her personal life. That became clear in 2003, when Moore began dating former That '70s Show star Ashton Kutcher, who was 15 years her junior. The two were married by 2005, but eventually divorced in 2013. 

While the relationship was already an iffy issue for anyone who was uncomfortable with their age difference, it also raised eyebrows because Kutcher was closer in age to Moore's eldest daughter, Rumer Willis (Moore was born in 1962, Kutcher in 1978, and Rumer in 1988). In fact, Rumer even admitted to having a crush on Kutcher before he got together with her mother. Now, that's just awkward.

Things didn't seem to smooth over during the marriage either, a time when Moore's daughters said that they didn't recognize their mother. Moore sat down with Rumer, Scout, and Tallulah to have an open and honest conversation about their past during an episode of Jada Pinkette Smith's Facebook show Red Table Talk in November 2019. During the interview, Rumer explained that while she had never seen her mother "not be in control around a man," Moore apparently lost herself around Kutcher (via Yahoo! Entertainment). Rumer claimed that she started asking herself, "Who is this person? I don't know who this is."

Demi Moore's attempt to have a baby with Kutcher caused resentment

While sitting down for their mother-daughters Red Table Talk interview in 2019, Rumer Willis opened up about the fact that her famous mom had wanted to have a baby with Ashton Kutcher while they were married — something that caused resentment and judgment, even within the family. Demi Moore's eldest daughter admitted, "When she wanted to have another baby and then it wasn't happening, and there was so much focus on that, it was like, 'Oh, well we're not enough'" (via the New York Daily News).

Even after Moore had gotten pregnant and endured a miscarriage at almost six months, Rumer was still admittedly unhappy, saying, "I think after you had a miscarriage, I literally was just like, 'Why are you so desperate to have another kid?'" She confessed, "I couldn't stand the idea." 

But then Rumer found photographs from when Moore had been pregnant. In one shot that was shared on Red Table Talk, Moore could be seen showing off her bare stomach and large baby bump. "I found these pictures, and I was like, 'Oh my god,'" Rumer said (via Just Jared). "I saw how big her stomach was, and I was like, 'Oh my god, I was so insensitive. I never once went to you and said, 'I'm so sorry' [or] 'Are you okay?'"

She went public about her threesomes with Ashton Kutcher

Engaging in an adventurous private life isn't necessarily scandalous — depending on who you ask — but Demi Moore's choice to open up about a personal situation that occurred with ex-husband Ashton Kutcher certainly sparked plenty of heated headlines. According to Radar Online, Moore claimed that she agreed to Kutcher's request to engage in threesomes while they were married in her Inside Out memoir. Explaining that she "wanted to show him how great and fun [she] could be," Moore admitted that it was a "mistake." 

The actress also wrote that when Kutcher reportedly cheated on her with another woman in their home, he allegedly tried to "deflect blame." She wrote, "Because we had brought a third party into our relationship, Ashton said, that blurred the lines and, to some extent, justified what he'd done." On Moore's side, she claimed the supposed infidelity made her feel "sick to [her] stomach."

While Kutcher didn't directly respond to any of the claims Moore made in her book, he did hop onto Twitter the same day it was released to write, "I was about to push the button on a really snarky tweet. Then I saw my son, daughter, and wife [actress Mila Kunis] and I deleted it." That was probably for the best.

Demi Moore's addiction turned her into a 'monster'

During their 2019 Red Table Talk interview, Demi Moore and her daughters, Rumer, Scout, and Tallulah Willis, addressed the actress' battle with addiction. Tallulah revealed that Moore became a "monster" when she wasn't sober, and admitted that her mother's behavior caused a lot of stress (via E! News): "I remember, there's just the anxiety that would come up in my body when I could sense her eyes shutting a little bit more, the way she was speaking, or she would be a lot more affectionate with me if she wasn't sober." Rumer added, "It was jarring."

Rumer also once had to call 911 during a party in 2012, when her mother had a bad reaction to drugs which resulted in a seizure. Moore talked about the incident during an interview with Good Morning America, saying, "My daughter [was] terrified that she was gonna see me die right in front of her. And within me, I was in a place that was thinking, 'Wow, how did I get in here?'" 

Thankfully, Moore was able to pull through and said, "I think it was a moment that I ... was somehow being given a choice." The choice she made was to get sober. She later wrote her memoir with the hope that by "sharing of [herself] in a way," it "can elevate or open someone else to loving themselves a little bit better."