1. When Mark Waters—who'd directed Lindsay Lohan in Freaky Friday—visited the actress in Toronto while she was filming Confessions of a Teenage Drama Queen, he asked her if she wanted to be in his movie. And she had one role on her mind.
"I wanted to play Regina. I had just played—in Confessions and Freaky—not the cool girl in school," she recalled to Entertainment Weekly in 2014. "I was still 17 years old and I wanted to be the cool girl on set." But between the trouble finding a Cady strong enough to go up against her Regina and the huge success of Freaky Friday, it became clear to the powers-that-be that a change was necessary.
"Sherry Lansing, who was heading Paramount at the time, told us, 'We have to have Lindsay play the lead in Mean Girls. It's just not going to work having her play the villain, because she now has an audience that won't accept that,'" Waters told Vulture in 2014, revealing it was up to him to break the bad news to the actress. "Lindsay kind of begrudgingly said, 'Okay, I guess I'll play the lead. At least I get to have more lines.'"
2. Before Waters swapped Lohan out of the Regina role, he had several actresses come in and read opposite her as Cady. One of them was then-24-year-old Rachel McAdams. "I remember watching her do the scene," Waters told Vulture, "and after it was over, I told her, 'I think you're a movie star, but you're way too old for this character. You just aren't going to be able to play the ingenue.' And she said, 'No, I understand, I get it.'" When it came time to find a new Regina, however, casting McAdams became a no-brainer. As she told EW, "Mark said, 'I see Cady a little bit younger, but I think it makes sense if Regina kind of grew up a little too fast.'"
3. Before McAdams could be handed the role of Regina, however, she had to sway the director away from another future co-star: Amanda Seyfried. The Mamma Mia! actress was a serious favorite for the villainous lead prior to becoming the delightfully daft Karen. "She tested for Regina and was kind of brilliant, and very different than Rachel's approach. She played it in a much more ethereal but still kind of scary way. She was more frightening, but oddly, less intimidating," Waters recalled, before adding that it was producer Lorne Michaels who suggested her for "the dumb girl."
He continued, "So she came in and read it and nailed it, and we got the best of both worlds."
4. While it seems impossible to imagine Mean Girls without SNL legends Tim Meadows and Amy Poehler in the roles of Mr. Duvall and Mrs. George, respectively, Waters admitted that Paramount was wary. "It's weird, but Paramount had a nervousness about Saturday Night Live," he told Vulture. "They'd been burned on some Saturday Night Live movies that had come from Lorne , so they didn't want many Saturday Night Live actors in Mean Girls, because then it might feel like an SNL movie and people might shy away from it." Meadows, who'd starred in the flop adaptation of The Ladies Man for Paramount, took "a lot of fighting with the studio," Waters added.
5. It's a good thing that Waters got Poehler cast because she wound up being integral in bringing mathlete Kevin Gnapoor's talent-show rap to life. In fact, Fey left it up to her former Weekend Update co-anchor to pen the bop for actor Rajiv Surendra. "She'll actually give credit to Amy for this, because Amy is more of the rap person," Waters revealed. "Amy definitely coached him on how to do the rap, and she actually gave him some of the moves and choreography for it."
6. When Paramount handed Mean Girls over to the MPAA for the ratings board, they tried to slap the teen comedy with an R rating, if you can believe it. And the studio had to fight back to ensure that the intended audience for the movie could actually go out and see it. "Even in the PG-13 movie, we had to take a lot of things out," Fey told Variety in 2018. "I remember thinking, If this was a movie about a boys' school, 'Is your cherry popped?' wouldn't have to come out." That line was replaced with the much tamer "Is your muffin buttered?" Not everything was a concession on the filmmakers' end, however.
“The line in the sand that I drew was the joke about the wide-set vagina," Waters told Vulture. "The ratings board said, 'We can’t give you a PG-13 unless you cut that line.' We ended up playing the card that the ratings board was sexist, because Anchorman had just come out, and Ron Burgundy had an erection in one scene, and that was PG-13. We told them, 'You’re only saying this because it’s a girl, and she’s talking about a part of her anatomy. There’s no sexual context whatsoever, and to say this is restrictive to an audience of girls is demeaning to all women.’ And they eventually had to back down.”
7. While it was Jonathan Bennett who was lucky enough to ask Lohan what day it was—October 3!—there were a few other contenders for the Aaron Samuels role. In a 2014 interview with Cosmopolitan, Daniel Franzese (who played Damian) revealed that the part originally belonged to a recognizable actor who got himself fired at the table read. "This other actor hadn't shaved and he didn't take his hat off; he was playing it really cool," Franzese said, afraid to ID the actor and embarrass him. "People kept coming over to him like, 'You know, you should really take your hat off.' And then, right after the table read, he got fired and they called Jonathan Bennett, who I guess was their second choice."
8. And that's not all Franzese spilled. "Also, Lindsay recently told me that, even before [the actor who got fired], James Franco was considered for the role of Aaron Samuels," he added. "I thought that was so cool—Bennett was great but that would've been cool."
9. While Bennett may not have been the first choice for Aaron, the actor contends that he got the gig because he bore a striking resemblance to Fey's former Weekend Update co-anchor Jimmy Fallon. As he told Huffington Post in 2015, "She said that's exactly 100 percent true."
10. As Fey explained to Entertainment Weekly in 2014, "I tried to use real names in writing because it's just easier." Case in point? The addressed-but-hardly seen Glen Coco, named after her older brother's good friend.
"He's a film editor in Los Angeles, and I imagine it's a pain in the butt for him," she explained to the publication. "Someone said to me you could buy a shirt at Target that says 'You go, Glen Coco!' That was unexpected." Other characters named after real people? Lizzy Caplan's Janis Ian, named after the musician who was one of the earliest musical guests on SNL, and Damian, named after Fey's high school BFF—and current TV Guide writer—Damian Holbrook. Cady, meanwhile, was named after Fey's college roommate Cady Garey.
11. Aside from writing the movie's killer script, Fey also starred in Mean Girls as math teacher and Mathletes advisor Ms. Norbury. But when it came to the math jargon she scripted for herself to say, she had no idea what she was talking about. "It was an attempt on my part to counteract the stereotype that girls can't do math. Even though I did not understand a word I was saying," she told the NYT back in 2004 before revealing exactly how she made those moments in the script make sense. "My friend's boyfriend is a calculus teacher in the Bronx. I took his lesson plans."
12. Mean Girls is based on Rosalind Wiseman's parenting book Queen Bees and Wannabees: Helping Your Daughter Survive Cliques, Gossip, and Other Realities of Adolescence, and, since it has no fictional narrative to adapt, Fey was free to draw from her own high school experiences to create a plot while staying true to what Wiseman's book.
And the author has remained enthusiastic about Fey's interpretation of her work, except for one minor thing. "I do not do trust falls, I have never done trust falls, I will never do trust falls," she told The Atlantic in 2014. "I just remember when I saw it the first time being like, 'Tina, I do not do that.'"
13. Remember that scene where Poehler's Mrs. George is holding her dog, oblivious to the fact that it's gnawing on her breast implant? Here's how they accomplished that. "They, like, pinned a piece of a cocktail wiener into her bra," McAdams told EW. "I thought this dog was going to tear her apart. It was very effective. She was such a pro through it. She's trying to do her lines and being so professional, and this dog is chomping on her fake boob. I'll never forget that."
14. According to Franzese, the initial script contained a scene for Damian that was cut before it was even filmed. "The original ending shows what happened to Damian after [junior year], and he was going to audition for American Idol. Simon Cowell was going to call him chubby and then he was going to run up on the stage and punch him," he told Cosmo. As the actor told the magazine, there were a lot of revisions to the original ending, including a bit where Ms. Norbury busts Kevin G for selling ecstasy, so when she's investigated for being a drug pusher, there are actual drugs in her desk.
"Janis and Damian convince Kevin G. to go to the school board when they discuss her punishment to confess that it was him, but Kevin G never shows up," he continued. "So Damian gets on the podium and kind of bulls--ts his way through saying it was him to try to protect Miss Norbury."
15. Fey famously never considered writing a sequel to the hit film, a decision she's gone on record as regretting. "At the time we did want to start the conversation about the sequel, and for whatever reason I was like, 'No!!! We shouldn't do that!'" she told EW in 2014. "Now I look back and I'm like, 'Why?' But now, no—it's too late now."
As she told Variety in 2018, however, "Maybe it's better, because we can save all the energy for this." This being the Mean Girls musical she wrote with husband and 30 Rock composer Jeff Richmond that premiered in 2017 before opening on Broadway in April 2018. Nominated for 12 Tony Awards and nine Drama Desk Awards that year, it won Fey the award for Outstanding Book of a Musical at the latter and served as inspiration for 2024's Mean Girls musical.
And while there's been no sequel ever made, there has been a film produced bearing the moniker Mean Girls 2. The made-for-TV "sequel" aired on ABC Family (now Freeform) in 2011 and was a stand-alone story that had nothing to do with the original film aside from having Tim Meadows reprise his role as the school's principal. It was not well-received.