During the late 1990s, several years after its launch in the U.K., Maxim magazine rose in popularity in the U.S., quickly becoming one of the top men’s publications on the market. Walking a fine line between other magazines geared towards guys, such as the fashion-centric GQ and scandalous, explicit Penthouse, Maxim’s mission was — and continues to be — to produce content that, as its official tagline reads, “promises to seduce, entertain and continuously surprise readers.”

Since its inception, the most highly-anticipated feature of Maxim has been the cover girl emblazoned on the front of each issue. Typically, it’s a well-known actress who is experiencing major success in her career. Each completes an interview for the magazine and partakes in a photo shoot while scantily clad, some more so than others, and many go on to earn coveted spots in Maxim’s annual Hot 100 compilation.

During the magazine’s peak years — arguably the late ’90s and early 2000s — numerous actresses appeared on the cover of Maxim. While a number were thrilled to have the opportunity, others had some regrets about their decision to be featured in the men’s magazine. And we bet there’s some who posed that you didn’t even know about.

In October 1999, during the height of Melissa Joan Hart’s career as the titular character on “Sabrina the Teenage Witch” (a role that she has a negative take on the idea of reprising), the then 23-year-old posed for the cover of Maxim. The shoot featured Hart, her hair mussed, both draped on a couch in black lingerie with the top undone and sprawled on a bed with a sheet barely covering her body.

Little did Maxim readers know at the time, but Hart had a wild night prior to the shoot, arriving for the sessions still high on Ecstasy. Shortly after the shoot, while at the premiere for her rom-com “Drive Me Crazy,” Hart received some devastating news. “My lawyer shows up and goes, ‘You did a photo shoot for Maxim magazine?,'” she recalled on the Pod Meets World podcast. “I’m like, ‘Yes, I did.’ They’re like, ‘Well, you’re being sued and fired from your show.'”

Though Hart initially thought her career was in jeopardy because of the racy shoot, it was the words on the cover — “Sabrina, your favorite witch without a stitch!” — that caused an uproar. As part of her contract with Archie Comics, Hart agreed to never play the character of Sabrina Spellman in the nude. “That was supposed to be me promoting my movie, it wasn’t supposed to be a character,” she said of the images. “I had no control over what they wrote on the cover.” Luckily, Hart was not fired and continued to star on the magical sitcom for four more years.

For three years, from 2001 to 2004, Hilary Duff was an icon among kids, tweens and teens thanks to her hit Disney Channel series “Lizzie McGuire” and youth-friendly rom-com “A Cinderella Story.” However, like most kid stars, Duff didn’t want to be stuck with that wholesome image for the entirety of her career, with the actress eventually taking steps to branch out into fresh endeavors.

Duff was actively shedding her Disney persona by 2009, appearing in the indie film “According to Greta,” releasing the song “Reach Out” – a far cry from early hits like “So Yesterday” — and appearing as Maxim’s January cover girl as part of a special Young Hot Hollywood edition. “Mothers come up to me and say, ‘Don’t ever change, you’re such a good girl.’ I am a good girl. But how can I say I won’t ever change?” Duff, then 21, told Maxim. “That’s impossible. And trust me, being a really good girl can work against you.”

Elsewhere in the interview, Duff discussed what drew her to a drama like “According to Greta,” rather than something else Disney-esque. She explained, “I see an acting career lasting longer than a singing career. I’ve been thinking of the long term. ‘Greta’ is an indie picture, which I love. The character’s obsessed with suicide. She’s funny and artistic and impossible not to like. I felt like I related to her exactly — minus the suicide part.” Given her preference for more mature roles, Duff was disappointed over the scrapped “Lizzie McGuire” reboot storyline that was too explicit for Disney.

After making a name for herself on Nickelodeon’s “The Amanda Show,” Amanda Bynes transitioned into a big screen star, appearing in hits like “Hairspray,” “She’s the Man” and 2010’s “Easy A.” Several months prior to the latter film hitting theaters, the 23-year-old Bynes was named “America’s Sweetheart” by Maxim and appeared as the cover girl for February. She sported two looks in the photo spread: a black lingerie set as well as a pink set with a white covering.

For Bynes, it was an honor to receive a call from the popular magazine. “This was my first sexy photoshoot. I was in lingerie, I was in high heels … and it was really fun. It was really cool because I felt sexy, but it was classy and it was really cool. I feel like I’m becoming a woman,” she said in a behind-the-scenes interview with Maxim.

That same year marked the end of Bynes’ acting career, with the star announcing her retirement on Twitter after being less-than-thrilled with how she looked on screen in “Easy A.” She told Paper in 2018, “I saw it and I was convinced that I should never be on camera again and I officially retired on Twitter, which was, you know, also stupid.” Three years later, Bynes experienced a public breakdown and was placed under a conservatorship by her mother through 2022.

Throughout the ’90s, Danielle Fishel graced TV screens across the country every Friday night as Topanga Lawrence on “Boy Meets World,” part of ABC’s family-friendly “TGIF” lineup. Unlike many child actors who look to distance themselves from their early roles as they get older, Fishel embraced her popularity as Topanga, returning to the character in 2014 on Disney Channel’s “Girl Meets World,” which ran for three seasons.

In April 2013, after news broke of the spinoff series, Fishel posed for the cover of Maxim in a beige bra and blue cardigan while holding a vintage telephone to her ear. Another shot from the session featured her posing with a vacuum cleaner while donning a white bra and blue skirt.

She shared in the interview with Maxim (via The Hollywood Reporter) that her “Boy Meets World” days mean just as much to her as they do the fans. “We were in people’s family rooms every Friday for seven years,” she said. “When I watch old episodes, it’s like watching home movies, so I imagine that other people feel the same way. ABC’s ‘TGIF’ lineup was probably the one time a week when parents and kids all watched TV together.”

Over the span of 13 years, Jennifer Love Hewitt, of “I Know What You Did Last Summer” and “Ghost Whisperer” fame, was featured on the cover of Maxim four times — in November 1999, March 2005, May 2009 and April 2012. In fact, she was named the magazine’s Sexiest Cover Girl of All Time.

For Hewitt, it was a thrill to pose at various points in her life and career. During a behind-the-scenes interview with Maxim for her 2009 shoot, she said, “I’m a Maxim girl, I like it. It’s nice for me because I’ll be able to take the three covers and put them through as who I’ve been in all the different stages of my life because the first time, I was really young. And then I was kind of young, and then I just turned 30, so it’ll be nice to go back and say, ‘See? Mom was hot one day.'”

During her 2012 interview with Maxim (via E! News), she candidly revealed her favorite body part to show off: her breasts, which she (somewhat) jokingly told USA Today that she would insure for $5 million if presented with the opportunity: “I’d be like, ‘Do it. Love it! Why not?'”

Lindsay Lohan graced the cover of Maxim in September of both 2007 and 2010. While the “Mean Girls” star’s inaugural appearance featured her in a series of non-revealing dresses, she opted for a black-and-white striped bikini for the second one, with many seeing it as a nod to her impending jail time.

In late summer of that year (the photo shoot was done in June), Lohan was expected to complete a 90-day jail stint after a series of run-ins with the law, which included attending an MTV Movie Awards afterparty while wearing an alcohol-monitoring SCRAM device following her 2007 DUI arrest. She ended up only having to spend 14 days behind bars before she was transferred to a rehab facility.

At the time of her second Maxim interview, Lohan was 23 and hopeful for a future of no longer making negative headlines. She said (via E! News) her main goal was “to focus on myself and my work and to move all press on me to focus on the work I do.” Though the next several years were fraught with more jail time, probation violations and concerning tabloid headlines as she struggled with addiction, Lohan eventually reclaimed her life. She’s now a proud wife and mother, and continues to be a force to be reckoned with on the big screen as she returns to the role of Anna Coleman in the highly-anticipated “Freakier Friday,” a sequel that co-star Jamie Lee Curtis pitched to Disney.

It was in July 2003, the year that “Charlie’s Angels: Full Throttle” hit theaters, that Cameron Diaz was emblazoned on the cover of Maxim for the first time. Sporting a white bikini, she was pictured seductively posing in the middle of her two “Charlie’s Angels” co-stars Lucy Liu — who had a solo cover in September 2002 — and Drew Barrymore.

While Barrymore never had a cover of her own, Diaz returned to Maxim eight years later as the cover girl for the June 2011 issue. Though she wore a western-esque ensemble for the carwash cover shot (a cropped flannel with low-rise denim shorts), the inside photos showed her as a provocative educator in a nod to that year’s flick, “Bad Teacher.” “Well, it’s the first time for a magazine!,” she told Maxim (via OK!) of her classroom look, which included a skin-tight dress, glasses and an apple. “I think ‘sexy teacher’ is one of the first on the checklist of fantasy costumes for most guys.”

“Bad Teacher” marked one of her final films before Diaz quit acting, though she has since resumed her career to film the Netflix comedy/action movie “Back in Action” and lend her voice to Fiona in “Shrek 5.”

Best known for starring in almost every “Resident Evil” movie as well as “The Fifth Element,” Ukrainian-American actress Milla Jovovich appeared as the Maxim cover girl in the U.S. for the September 2009 edition, with the same shoot used for the Australian version of the magazine in March 2012.

While some of the shots depict Jovovich in a two-piece black lingerie set, others are reminiscent of Melissa Joan Hart’s risqué cover, with a white sheet barely covering anything. In her interview with Maxim, Jovovich revealed that she had the option to wear as much or little as she preferred, with a number of dresses at her disposal if she wanted something more modest. However, that’s not the vision she was aiming for. “I was like, ‘Look, I do Vogue, OK? I’m not doing this to advertise a designer — I’m doing this to show my body. Lingerie and a sheet, OK?,'” Jovovich recalled.

Elsewhere in the interview, when asked how she felt about being a “dream girl for geeks” given the nature of her filmography, especially the “Resident Evil” franchise, she explained that she embraced it: “I love that, man! I think it’s great because it means that smart men like me. Plus, nerdy guys are always the cool ones in the end. I mean, who wants to date a stupid jock?”

From “Scary Movie” to “American Pie,” Shannon Elizabeth was one of the “it” girls of the late ’90s and early 2000s. Naturally, this status earned her a spot as Maxim’s cover girl not once, but three times, in January 2000, December 2003 and June 2008. Elizabeth chose a slightly different look each time, transitioning from a beige corset to a white tank and shorts to an off-white mini dress, bra slightly showing over the top.

In an interview for Maxim Australia’s October 2020 issue, Elizabeth looked back on her three cover girl experiences with nothing but positivity. She said, “I mainly remember always being in great hands when I’d shoot with Maxim. I always knew we would have the best photographer, hair, make-up and wardrobe. The pictures were always stunning, too!”

Elizabeth also discussed a variety of other topics in the interview, including her decision to stop eating meat, how Buffy in “Scary Movie” was her favorite character to play, and the pride she took in her charity work for animals through the Shannon Elizabeth Foundation.

Alyssa Milano was selected as the Maxim cover girl for the March 1998 issue, coinciding with the premiere of “Charmed” (from which she allegedly got Shannen Doherty fired) on The WB. For the shoot, the “Who’s the Boss?” actress wore tie-up leather pants and alternating black and white tank tops. Fifteen years later, at the age of 40, while promoting her new drama series “Mistresses,” Milano returned to Maxim’s cover for its July 2013 edition, this time rocking white underwear and an unbuttoned blue flannel with nothing underneath.

During her latter interview with Maxim, Milano reflected on being a child star in the ’80s, which came with its share of awkward moments. “It wasn’t weird, because I didn’t know any different. You know, I went through puberty like everyone else,” she said (via The State Journal-Register). “It only got embarrassing when the show would take what was going on with me and write it into the show, like ‘Samantha’s First Bra.’ It was like, ‘Okay, guys, do we really need to do this?’ But what an awesome time stamp!”

In 2006, Kristen Bell was becoming a household name thanks to her portrayal of the titular character on the drama series “Veronica Mars,” which premiered two years prior and would go on to enjoy four seasons over the span of 15 years. As was the tradition for hot commodity actresses, Bell appeared on the March 2006 cover of Maxim, wearing different iterations of black lingerie, sometimes with a black cardigan falling off her shoulders.

But while some cover girls, such as Amanda Bynes and Jennifer Love Hewitt, saw their features in Maxim as opportunities of a lifetime, Bell didn’t remotely feel the same way. She candidly revealed in a 2009 interview with The Orange County Register that she did not want to do the photoshoot, but felt obligated to. “…I fought it at the time. You have no idea how much I fought it. It boiled down to choosing the lesser of two evils,” she said.

When prompted to explain what she meant by this, she revealed the other, stronger evil: “Angering some people I shouldn’t anger. I could have risked my career. So I did the magazine shoot. It’s not the route I would choose to go, but I had to do it and I tried to do it as tastefully as possible. I don’t want to be that type of actress.” Bell went on to say that, unlike other actresses in Hollywood, she didn’t consider landing a Maxim cover a rite of passage.

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