1. Before Freddie Prinze Jr. and Rachael Leigh Cook snagged the roles of Zack Siler and Laney Boggs, director Robert Iscove talked to several up and coming actors.
"I remember talking to Josh Hartnett for the role that Freddie did, and pretty much anybody who was young and either in a hit TV show or starting to break in features," he told The Daily Beast in 2014. "We went through a million girls for Rachael's part—from Leelee Sobieski to Mena Suvari to Jordana Brewster."
2. After Prinze was cast as the high school president and star athlete, the character was slightly rewritten.
"I made him a little sweeter probably than he was originally written and that allowed a bit of vulnerability there," Prinze explained to Today, "so that when he did mess up but he felt bad for it, people gave him some sympathy rather than saying, 'Ahh, he's a jerk!'"
3. Cook recalled Prinze struggling to film the climactic scene in which Laney confronts Zack, asking, "Am I a f--king bet?!"
"He was kind of emotional in that moment," she revealed to Today, adding that she remembered "he was kind of choked up and that was definitely the cutest thing I'd ever seen."
4. In 2013, controversy ignited when M. Night Shyamalan alleged he "ghost-wrote" the script, a claim credited screenwriter R. Lee Fleming Jr. vehemently denied. But, according to Jack Lechner, who served as Miramax's head of development in the late '90s, neither writer is wrong.
"He did a solid rewrite," Lechner told Entertainment Weekly of Shyamalan's contribution. "He made it deeper, made the characters richer."
Specifically, producer Richard N. Gladstein told E! News, The Sixth Sense auteur's tweaks "helped enormously with the relationship with Kevin Pollak [who played Laney's father, Wayne]," but that the script "was pretty much done" by the time it made its way to him.
5. While it became one of the most memorable scenes in the movie, Cook admitted to feeling "self-conscious" while filming Laney's slo-mo walk down the stairs to reveal her makeover to Zack.
"There were two of that dress. We needed a stunt double dress for the scene where I had to run out and fall down in the driveway," Cook explained to Entertainment Tonight. "One dress felt a good size smaller than the other one. Apparently the [main dress] was not available, so I'm in the second dress just going like [holds breath] to get down the stairs. Just without breathing. Say some words and then we'll be done!"
6. Costume designer Denise Wingate explained to Interview magazine why Laney had to be wearing red in that pivotal scene.
"Up until that point her palette was very drab," Wingate said. "That's why when she comes down the stairs to meet Zach that moment was more about the color than the dress itself. It was this bold statement of her dressing in a color that was so different than anything we'd seen her in before."
7. Sorry to burst your bubble, but Prinze admitted to Today that he needed a double for Zack's infamous hackeysack performance because the actor did, in fact, let it drop many times.
"I thought I was going to get good at it, as they said they had a trainer for me. I didn't realize how long it would take," Prinze recalled. "It was the day of and Rob said, hey, we're going to shoot the hackeysack scene.' I was like, 'Man, I can only get it four times in a row.' He said, 'I know, don't worry. We've got a world champion hackeysacker and he looks a lot like you. He's a good double for you.'" I was like, 'Oh cool!' And so if you watch the scene again, you'll see your boy…I think I got three in a row on a good take…so the first three are me!"
8. Remember that over the top falafel hat Laney had to wear at her job? "I actually asked for a falafel hat, that was my idea," Cook revealed to Today. "So I did that to myself."
9. Matthew Lillard demanded a personal trainer before signing on to play Brock Hudson, the MTV reality star boyfriend of mean girl Taylor (Jodi Lynn O'Keefe).
"He's like, 'Because I want to be buff if I'm going to be in the pool,'" Iscove explained to Cosmo of the actor's request. "And we went, 'OK. You want to be buff, be buff.' So he did. He spent two months with a trainer and then we did his Real World stuff in the beginning, which I shot on video actually, where the rest of the movie was on film."
10. "Kiss Me" by Sixpence None the Richer hit number two on the Billboard Hot 100 after being featured in the movie, going on to stay in the Top 10 for 16 weeks. In Europe, the movie's title was changed from She's All That to Kiss Me.
11. Rapper Lil' Kim made her acting debut as Alex, one of the popular girls. "So the rumor got out that Freddie and I wore Lil' Kim's wigs," Cook told E! News. "I really hope Lil' Kim's not watching this because that is 100 percent true. I'm sorry, they're magnificent, and they were just there. I'm only human, of course I was going to put on Lil' Kim's wigs!"
12. A few sneaky pop culture references made their way into the movie through the main characters' names. Laney Boggs was an homage to two of Winona Ryder's roles: Lelaina "Laney" Pierce in Reality Bites and Kim Boggs in Edward Scissorhands. Zack and Taylor, meanwhile, were references to members of the band Hanson.
13. Before he played Jess on Gilmore Girls, Milo Ventimiglia had a small role as one of the J.V. soccer players Zack recruits to clean Laney's house.
14. The high school the movie was filmed at is the same campus used for Buffy the Vampire Slayer and Beverly Hills, 90210.
15. Speaking of Buffy, Prinze's future wife Sarah Michelle Gellar made a quick cameo as the high school student who passes on some fresh ground pepper.
"She was there visiting Freddie and we asked her if she would come and do it, and she said she would come and do it, but she wouldn't speak," Iscove told Cosmopolitan. "She wouldn't say any lines. OK, we don't know why you wouldn't say, 'Thank you,' or 'No.' But that was her thing and she did it. And to get Buffy in the movie was certainly [a big deal]—because at that point, Buffy was huge."
And, as Gellar joked on Instagram, "I think you really understood that my character did not want pepper."
16. Iscove had to fight to keep the now-iconic prom scene in the movie, explaining to Cosmo he really "wanted a big dance number" despite the studio's reservations. The solution: More scenes with Usher, who played the school's D.J. (Hey, it was the '90s!)
"That's why we went back and shot more Usher stuff [of him] saying 'Remember what I taught you in dance class' or whatever," he said. "We went back and shot more scenes with Usher in Chicago, which was where he was doing an album, and intercut more."
17. One person who was not happy with the dance number was Dulé Hill, who was "pissed that he wasn't able to tap dance," according to Prinze.
"Dulé's this world-class tap-dancer," Prinze told The Daily Beast. "When we were shooting the volleyball sequence at the beach, I heard him sliding and tapping his feet on the wood, and I said, 'Are you tap dancing?' And he said, 'I'm a hoofer, man.' And that's how we bonded. We started going to this dance studio in Hollywood and we'd tap dance. We did it all the time."
18. The number was choreographed by Adam Shankman, who would go on to direct A Walk to Remember, The Wedding Planner and Hairspray, among other films. Prinze and Shankman immediately hit it off while filming the movie, so much so that he played a large role in Prinze's 2002 wedding. As he told Today, "The choreographer from She's All That married my wife and I!"
19. In an interview with E! News, Cook admitted she "was a little intimidated" by the late Paul Walker, who tragically died in a car crash in November 2013 at the age of 40. "[He] was an awesome actor, but he didn't act actor-y," she recalled. "He seemed like a surfer who somebody picked off the beach and dragged onto a movie set—who happened to be good at acting."
"He wasn't hyper-social, he sort of just did his work and kept to himself," she added. "I think that I was a little bit intimidated by him—plus he's really tall and was super hot, so respect to that. Just, wow."
20. The Internet freaked out over Prinze and Cook's IRL reunion in 2016, with the latter revealing it was Walker's tragic death that ultimately inspired their meet-up.
"I remember in 2013, right after Paul died very, very suddenly, thinking to myself, Wow, life is incredibly short. I should reach out, I should say hi. He's someone who I care about, he's someone who I would want to see again," Cook explained to Today of contacting Prinze. "It had been a million years then and somehow it took me another three years after that to reach out and say, 'Hey, I know we're not day-to-day friends, but it would be great to see you.' So we caught up over an epic coffee and pastry selection."