Hilary Duff's Most Controversial Moments Ever

This article references eating disorders and racism. 

Weaned on the showbiz nourishment that only a giant like Disney could provide, Hilary Duff has managed to sidestep the pitfalls that await a child star once Mickey Mouse's guardianship gives way to the harsh realities of adulthood. Part of that has to do with her charm as the titular misfit character of "Lizzie McGuire." The show attracted a youthful audience to the family channel, and it ran for three seasons until 2004. 

While Duff's photogenic qualities were given, it was her ability to portray an adolescent oddball caught up in situations out of her element that made her relatable to audiences. She's considerably extended her career parlaying that element. That's been evident in her portrayal of the gaffe-ridden Kelsey Peters in the Paramount+ offering "Younger" and scatterbrained Sophie in the Hulu-streamed "How I Met Your Father." Both of these were arguably delivered while her peers struggled with an over-the-hill teen celebrity stereotype that would eviscerate their careers.

Duff has confidently declared that if given a second chance, she'd take the child star route again. "I wouldn't do it all exactly the same, but I can't look at my life and be like, 'I wish this was different,' because I don't know if it would get me to where I am right now," she said to Cosmopolitan. Still, that doesn't nullify some bad decisions that could have wreaked havoc with her livelihood, including questionable relationships, public feuds, and the occasional inability to pick up on social cues. Here's a look at a few stains on her otherwise squeaky-clean image.

Early in her career, Hilary Duff found herself on the receiving end of shade thrown by Lindsay Lohan, then one of Hollywood's best-known teen actors, having made a name for herself in the remake of "The Parent Trap." It all started when Duff and late singer Aaron Carter started dating in 2002, before he dropped her in favor of Lohan a year and a half later. That tête-à-tête lasted only a few months before Carter hopped back to Duff. The reunion was short-lived and shut down for good after Duff found out Carter was philandering with yet another girl. As legend tells it, the two ladies then began a red-carpet Cold War that saw them attending each other's movie premieres. Was Duff even invited to the "Freaky Friday" premiere? And was Lohan really necessary on the "Cheaper By the Dozen" red carpet? We'll never know. But the feud was fired up, regardless.

In 2004, Lohan used her guest-hosting stint on "Saturday Night Live" to up the ante. During her opening monologue, featured player Rachel Dratch made an appearance with a truly unflattering portrayal of the star's rival. Speaking to USA Today, Duff insisted that she wasn't insulted. Nonetheless, she thought the sketch was mean-spirited, adding, "I don't think [Lohan] likes me very much." No kidding. By 2007, the conflict inexplicably ended. "We are both adults and whatever happened, happened when we were young," Duff told People. "It's over." All has been quiet on that Hollywood front ever since. 

Hilary Duff's "Lizzie McGuire" character went through several school crushes, finally getting her first kiss in the second season. But while Lizzie was still working on her romantic batting stance at home plate, Duff was allegedly rounding the bases away from the soundstage. After going out with the likes of Aaron Carter and "Cody Banks" star Frankie Muniz, 16-year-old Duff moved on to her first serious relationship. In 2004, she started dating 25-year-old singer Joel Madden, a pairing the two wanted to keep under wraps. "I think a lot of people had ... an issue with an age thing," Duff said on "The View" in 2005. "... We think it's kind of weird to make a [spectacle] out of everything."

As for how far the coupling went in the amorous department, Duff was vague, leaving her fans to connect the dots. "I had a 26-year-old boyfriend, so everyone can make their own assumptions about what I was doing," the actor told Cosmopolitan in 2015. If the couple did the nasty within their two year courtship, Madden would have found himself in a pack of trouble, given that the legal age for sexual consent in California is 18. Had the two been caught in flagrante delicto, Madden would likely have been nailed with a misdemeanor or felony, at worst facing up to four years in jail if found guilty.

Hilary Duff is seldom on record for starting a feud, but in 2004, she seemingly picked a target who wasn't afraid to shoot back. In this case, the crosshair dweller was Avril Lavigne, whom Duff criticized for apparently showing disregard toward fans who'd imitated her fashion sense. "I think some of the things Avril said about her fans were kind of mean-spirited," Duff told World Entertainment News Network (per Paper). "... I was like, 'You should be happy that these people like you and look up to you!'" Lavigne was not best pleased. Immediately, she retorted to Newsweek, "I'm like, 'Excuse me?' First off, it's not even true. I never said that. And second, who the hell cares what she has to say about my fans? Whatever. Hilary Duff's such a goody-goody, such a mommy's girl."

Lavigne later lashed into Duff on Boston FM station MIX 98.5 (per PopDirt), sniping, "I'm like, 'Who are you to talk about me? You should know better. Don't talk trash with me, you can go screw yourself." Quickly, Duff's publicity camp raised a white flag to quell the truce, sharing an apology for her statements while insisting that the whole situation had been grossly exaggerated. In a statement shared by "Access Hollywood," her team added, "Although she has never met Avril Lavigne, she is a big fan of her music."

On several occasions, Hilary Duff has found herself in hot water, most likely because she was naive or far removed from the social norms that more everyday folks had to follow. A case could be made for both reasons when in 2016, Duff and her personal trainer boyfriend Jason Walsh dressed up for a posh Halloween bash in Beverly Hills. Unfortunately, they obviously didn't get the memo about attire violating the cultural appropriation code, especially when their questionable choice of wardrobe wandered into racist territory (above). So it was perfectly understandable why the Twittersphere was rattled over photos of Duff in a pilgrim outfit, accompanied by Walsh in aboriginal buckskin, complete with a full chief headdress and war paint. 

The tweets came fast and furious, with comments responding to a Just Jared report of the costumes ranging from sarcastic ("The perfect white power couple!") to outraged ("This offends people, not at all okay. Why not just go in black face? Same thing"). 

Realizing that she had unwittingly overstepped some boundaries, Duff issued an apology on Twitter. "I am so sorry to people I offended with my costume," she wrote. "It was not properly thought through and I am truly, from the bottom of my heart, sorry." At the time of her wardrobe miscalculation, headdresses were already controversial talking points with several music festivals banning the item from their performance venues, with sports teams like the Kansas City Chiefs and the Chicago Blackhawks following suit a few years later.

After Hilary Duff was finished with the "Lizzie McGuire" series in 2004, she focused more on her recording career, although she managed to get movie roles in rather lightweight fare like "A Cinderella Story" and "Cheaper By the Dozen." Her chance to land a meatier opportunity arrived in 2009 by way of a lead role playing mobster Bonnie Parker in "The Story of Bonnie and Clyde," an adaptation of the classic 1967 drama "Bonnie and Clyde," which won two Oscars. 

But news of the casting wasn't exactly endearing to actor Faye Dunaway, who played Parker in the original outing, landing an Oscar nomination for her efforts. "Couldn't they at least cast a real actress?" she reportedly lamented, per Entertainment Weekly. Duff was hardly diplomatic in her retaliatory remarks to Dunaway, playing the has-been, ageist card for all its worth. "I think that my fans that are going to go see the movie don't even know who she is," Duff hit back to E! Daily 10 (per OK!). "I think it was a little unnecessary, but I might be mad if I looked like that now, too."

Dunaway didn't respond to Duff's comments, but eventually had the last laugh. Several months later, after Duff married NHL player Mike Comrie and while expecting their first child, she was cut from the Parker role. Per TMZ, producers denied her pregnancy had anything to do with the decision and paid her $100,000 for her dismissal.

Between recording stints and movie roles, Hilary Duff also took the occasional cameo contract on the prime-time television circuit, garnering appearances on such fare as "Joan of Arcadia," "Ghost Whisperer," and "Law & Order: Special Victims Unit." But by far, her juiciest role on the small screen took place in 2009 on the third season of The CW's "Gossip Girl" as recurring character Olivia Burke, a famous actor masquerading as a New York University student. Of the six episodes that included Duff, one included a potentially steamy scene that saw her character engage in a threesome with characters played by series leads Penn Badgley and Jessica Szohr. Naturally, The CW amped up the sensationalism surrounding the episode via a series of preview ads to garner more viewership, in the process catching the eyes of one disapproving lobby group.

When members of the Parents Television Council saw the "Gossip Girl" promos, the group's president, Tim Winter, sent a message to the network, urging them to yank the episode on grounds that it would negatively influence teens who watch the series. "'Gossip Girl' routinely depicts teenagers engaging in promiscuous, consequence-free sexual behavior, and that's bad enough," wrote Winters, per TV Fanatic. "But will you now be complicit in establishing a precedent and expectation that teenagers engage in behavior heretofore associated primarily with adult films?" The CW ran the episode anyway.

Hollywood is not only well-populated by actors, it also has a very healthy crop of lawyers. In 2012, Hilary Duff needed the expertise of a few of them. Two years earlier, a driver was in a collision with the star in a Range Rover at a West Hollywood intersection, and the individual sued her for unspecified damages. In papers filed for the lawsuit, the plaintiff suggested she had experienced "great mental, physical and nervous pain and suffering" from the incident, adding that her injuries would prevent her from doing her job for a protracted amount of time in the future, per TMZ. In 2015, Century City Westwood News reported that both parties decided to settle the case using binding arbitration.

Duff had an easier time handling a defamation lawsuit brought on her by photographer Darryl Wilkins, who she spotted snapping photos of a boys' soccer team. On Instagram, the star shared a video of herself confronting Wilkins and asking him to stop. When he refused, she published the footage, along with the caption, "Creep! Laws need to change! This is stalking minors! Disgusting!" In the video, the photographer tells Duff that his actions are legal and innocent, as he was practicing photography. Per Radar, Wilkins also sued producers of "The Wendy Williams Show," when the program covered the story. The judge dismissed the defamation suit on grounds of a California law that prevents lawsuits from impeding the right to free speech, per Spectrum News 1. 

For years, Hilary Duff has taken on gigs that would further distance herself from the perky innocence of her Lizzie McGuire character, even if her more nostalgia-minded fan base expressed concerns about her choices. "I don't want to restrict myself from doing things that stimulate me just to make them happy," she told Allure in 2009. "If they continue liking me, that's cool, but I don't want to cater to them. I'm not 13, 14, or 15 anymore." So when Disney came around to discuss the idea of revisiting "Lizzie McGuire" in 2019, this time as a woman in her 30s, Duff knew that there was no way they could tap the same creative veins responsible for the content that paralleled her days at Hillridge Junior High School.

Speaking to Cosmopolitan in 2022, she revealed that the premise was to have McGuire having to move back to live with her parents after ditching her boyfriend, whom she caught having an affair. Beyond that, the power brokers at Disney reportedly weren't too into Duff's ideas for her character. A year later, talks broke down, and the show was scrapped after Disney claimed that the show was too adult. "She had to be 30 years old doing 30-year-old things," Duff insisted to Women's Health. "She didn't need to be doing bong rips and having one-night stands all the time, but it had to be authentic. I think they got spooked."

While Hilary Duff's social life as a single person was an insatiable source of scandal for tabloids, her more recent days as a mother of three and a wife to musician Michael Koma have been remarkably untainted. Even her brief marriage to former Edmonton Oilers hockey star Mike Comrie hardly registered at more than a ripple on the sensationalism scale, making more waves in Canada than in the U.S. But early in 2022, distraught moms across America expressed their dismay over an Instagram video entry that involved one of Duff's children. The video featured 3-year-old Banks in the back seat with actor Molly Bernard, a pal from the time she and Duff shared the screen in the streaming series "Younger" who was watching over the youngster that day. 

But several viewers were alarmed that Banks was not sitting in a child safety seat, which is illegal in California. State laws reveal that any child under 8 has to be in a car seat or booster in the back, while those shorter than 4 foot 9 inches must at least be in a booster seat. It's also clear in the video that Banks isn't even secured by a seat belt. Duff seemed defensive in her response to the criticism. "It's not like I'm driving on the 405 with my kids in the backseat without a car seat," she said to Romper. "You have no context. You don't know where I am."

Hilary Duff's strategy of further disconnecting herself from "Lizzie McGuire" involved more than just picking some more adult-oriented roles. In 2022, She took a cue from a few other former child stars such as Miley Cyrus and Melissa Joan Hart and took part in a nude photo spread. But Duff made it clear that baring all for Women's Health was more than just a career decision, but rather a way to bring attention to the body insecurities she faced in the past, including eating disorders. While hardly graphic, her unfettered epidermic canvas was a testament to how she had succeeded in learning to love and accept herself. "I'm proud of my body," she said to Women's Health. "I'm proud that it's produced three children for me. I've gotten to a place of being peaceful with the changes my body has gone through."

Critics pointed out how Duff was praised for her images, while Britney Spears got trashed for posting her own Instagram nudes at roughly the same time. Much of the criticism directed at Spears appeared to be based on how the images were undignified and embarrassing for a mom of two teen sons. On Twitter, one user pointed out that Duff's photoshoot also missed the mark of its intended message, writing, "No shade to Hilary Duff, who looks incredible, but how is a conventionally thin and attractive woman with a post-baby six-pack redefining anything in Hollywood?"

If you need help with an eating disorder, or know someone who is, help is available. Visit the National Eating Disorders Association website or contact NEDA's Live Helpline at 1-800-931-2237. You can also receive 24/7 Crisis Support via text (send NEDA to 741-741).