‘She’s All That' 15th Anniversary: Cast and Crew Reminisce About the Making of the ‘90s Classic
The 1999 coming of age comedy She’s All That holds a special place in the hearts of millennials. On the movie’s 15th anniversary, the cast and crew open up about the making of the movie, memories of Paul Walker, M. Night Shyamalan’s contributions, and much more.
On January 29, 1999—exactly 15 years ago—a modern day adaptation of Pygmalion was thrust on an unsuspecting public. Filmed in sunny Torrance, California, and boasting a young, attractive, and mostly unknown cast, the MTV gen film was an odd fit for distributor Miramax, run by brothers Harvey and Bob Weinstein, who specialized in high-brow indie fare (one year prior, they'd taken home the Best Picture Oscar for the costume drama Shakespeare in Love). Despite this, and the fact that it opened over Super Bowl weekend, the effervescent teen flick shot to No. 1 at the box office, and earned a grand total of $103 million worldwide against a $6 million budget. It was a sleeper hit. In the 15 years since, due to the laundry list of stars it helped launch, its funky vibe, catchy-as-all-hell soundtrack, and phrases like “major wiggage,” “hoover it,” and “jump up my ass,” it's gone on to become a coming of age classic; a film that’s revisited by twenty-somethings time and again on cable.
I’m talking about She’s All That.
The film centered on Zack Siler (Freddie Prinze Jr.), the campus stud at a high school in Southern California. When he’s suddenly dumped by his ditzy girlfriend, Taylor Vaughan (Jodi Lynn O’Keefe), in favor of a vacuous ex-Real World star by the name of Brock Hudson (Matthew Lillard), Zack tries to salvage what’s left of his ego by deeming her replaceable. His soccer pal, Dean Sampson (Paul Walker) calls BS, and the two make a bet: Zack has six weeks to turn any girl Dean chooses on campus into prom queen. So, Dean picks Laney Boggs (Rachael Leigh Cook), a dorky, surly art student. And the fun begins.
In addition to the aforementioned central cast, director Robert Iscove’s film boasted many other big names in smaller roles. Kevin Pollak and Tim Matheson served as Laney and Zack’s fathers, respectively; Laney’s Sega-obsessed little brother, Simon, was played by Kieran Culkin; Oscar winning actress Anna Paquin was Zack’s sister, Mac; The West Wing’s Dulé Hill was Zack’s pal; Taylor Vaughan’s crew was played by Gabrielle Union—in her first film role—and rapper Lil Kim; and, last but certainly not least, Usher—yes, THE Usher—played the school DJ. Oh, and filmmaker M. Night Shyamalan even admitted to rewriting some of R. Lee Fleming’s screenplay.
She’s All That has gone down in history as one of the most popular teen movies of the ‘90s; a generational classic that introduced us to not only the next generation of actors, but songs like Fatboy Slim’s “The Rockafeller Skank,” which played during the film’s big dance number, and Sixpence None the Richer’s “Kiss Me,” the movie’s de facto theme song. It deserves its rightful place alongside the oeuvre of John Hughes, and was the last film reviewed in print by the late Gene Siskel, who gave it a positive review.
We reached out to the entire cast of She’s All That, and many of them were gracious enough to participate and share their favorite memories from the making of this ‘90s gem on the occasion of its 15th anniversary.
ON HOW TIME FLIES
Freddie Prinze Jr.: I didn’t even know the movie did that well, to be completely honest with you! This is so funny.
Rachael Leigh Cook: Man, I can’t believe it! It’s so crazy. I feel like so many things in my life have happened since then.
Matthew Lillard: I look back and just think, “Where the hell has all the time gone?”
Kevin Pollak: I think it's a damn well made film and am proud to be a part of a film that launched a number of amazing careers including Freddie and Rachael, of course, but also Paul Walker, of course. I didn't mention Usher because he was quite the star prior.
Jodi Lynn O’Keefe: This movie was so much fun for me. We had such a fun time. We were all peers, and young.
ASSEMBLING THE AMAZING CAST
Robert Iscove (Director): Harvey Weinstein gave the film to me. I was one of the many people that was involved with Chicago after I did Cinderella, and there were many problems and Chicago was being put on hold, so he said, “In the meantime, I have this great project that I want you to direct.”
Freddie Prinze Jr.: I think this was the first role I had ever been offered. I had done House of Yes for Miramax and Harvey Weinstein, and I’m pretty sure I was Harvey’s pick for this movie. And when you’re Harvey’s pick that’s it, whether they liked it or not!
Rachael Leigh Cook: Harvey had seen this movie I did, All I Wanna Do, with Kristen Dunst and Gaby Hoffman, where I play a kid in high school and apparently I was cast because of that.
Robert Iscove: 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. We went through a million girls for Rachael’s part—from Leelee Sobieski to Mena Suvari to Jordana Brewster. Every young girl we saw. She had to be beautiful, self-deprecating, funny, withdrawn, and all that. Rachael had done a movie for Harvey, All I Wanna Do, and I looked at it and he looked at it, and we said, “Yeah, let’s bring Rachael in.” Harvey is very involved in script development and very involved in casting. That’s how we got people like Kieran Culkin and Anna Paquin in very small parts. He’d say, “You do this for me, and I’ll do something for you.”
Freddie Prinze Jr.: My wife [Sarah Michelle Gellar] had known Kieran since he was 4 years old—she used to walk him home from school. Kieran’s a really great guy, and the only actor who’s more willing to turn his back on this industry than I am. And he’s totally happy.
Rachael Leigh Cook: I went to high school with Josh Hartnett! South High in Minnesota! That would have been wild.
Kevin Pollak: I was sent the script and liked it, but it wasn't until I heard that Freddie Prinze Jr. was the lead that I agreed to do it. You have to remember, this was before most people knew him as a film actor, or millions of teenage girls fell in love with his charming smile. I had seen him in a tiny dramatic film called House Of Yes with Parker Posey, and thought he was the absolute real deal.
Matthew Lillard: To be honest, I think it was my relationship with Freddie. He and I had just done that box office epic Wing Commander and became great friends while we were shooting in Luxembourg. He put in a good word, I met the creative team and they took a chance on me. It was a great job for me at the time and I have Freddie to thank.
Robert Iscove: The movie was filmed at the same high school as Buffy: The Vampire Slayer, and Sarah [Michelle Gellar] did a cameo in the film, but she refused to speak! For whatever reason, she wouldn’t say a line. We were just happy to have her. I think she was just starting to see Freddie at that point, although nobody was aware that she was just starting to see Freddie, because he had just broken up with his girlfriend.
Freddie Prinze Jr.: Sarah had a cameo, and we had done I Know What You Did Last Summer before this, but I think I was still with Kimberly [McCullough] at the time. I wasn’t with Sarah yet.
Tim Matheson: I had worked with Rob Iscove on a TV movie, Dying To Love You. He called and asked if I would jump into the part. I liked the script, the cast, and of course working with Rob. The tone of She’s All That was so different from Animal House that I never made any connection between the two films. She’s All That was so much sweeter than Animal House’s overtly political and anarchic tone. Being a modern retelling of Shaw's Pygmalion, it’s a love story, while Animal House is a larger comic tale of snobbery, elitism, and the class system.
Usher: I guess they couldn't find anyone cooler to play a dancer, DJ, and voice of a daily high school announcer. So I said what the hell, I'm your guy.
ON THEIR OWN HIGH SCHOOL EXPERIENCE(S)
Freddie Prinze Jr.: I was WHACK in high school. I had one friend who was a little nerdier than me, and look, I was sort of raised by my godfather and the strong men he knew, and my godfather was Bob Wall, the guy who first trained Bruce Lee when he came to America, so I didn’t know how to throw a football but I learned mixed martial arts. I went to the same high school in Albuquerque, New Mexico [La Cueva High School], as Neil Patrick Harris, and I remember him getting onstage and getting everyone excited about acting by doing an impression of Dudley Moore from Arthur. I was like, “BAM, that’s what I want to do.” I didn’t care about our 6’2” quarterback where it was as good for him as it was ever going to get. I wasn’t cool and kept to myself, and we had off-campus lunch, so when that bell ran I’d go off and sometimes never come back. High school was weird, man. I felt like I needed a passport to be there and I just didn’t have one.
Rachael Leigh Cook: I was pretty nerdy and kept to myself in high school! Not as much of a dork as Laney, though. I was into drama but wasn’t really into painting.
Jodi Lynn O’Keefe: The character of Taylor was fully based on life experience and girls that I had seen and known growing up when I was in middle school and high school. There’s always that girl who’s the most popular and the prom queen, and you feel like she has everything, and I was such an awkward nerd when I was in high school. I didn’t look anything like Taylor Vaughn in high school, and don’t think I came into my own until after.
THE SHYAMALAN INTERVENTION
Freddie Prinze Jr.: I didn’t know about the M. Night Shyamalan thing for probably a decade, and when someone brought that up, I thought, “That’s a bunch of BS, man!” because I’d never met him, and the script that was given to me said “R. Lee Fleming” on it. And there was some sort of writer beef or something? “Which dork will prevail in the steel cage of death!”
Rachael Leigh Cook: That M. Night Shyamalan thing totally floored me. When I heard that from my manager, I said, “Yeah, and I kidnapped the Lindbergh baby.” It made no sense to me whatsoever. But now, in terms of the hacky sack scene? Pretty much the same as Signs. It is amazing. I think you’ve convinced me to re-watch that scene.
Robert Iscove: M. Night’s big thing was addressing what the bet was really about, and he told us this story about a friend of his who made a bet in high school and then had to streak naked across the quad, so we then turned it into Freddie having to be naked at graduation at the end of the movie. And yes, M. Night did the performance art piece—and the hacky sack sequence—and he wrote a bit about what happened at the end of the party scene.
Freddie Prinze Jr.: It’s a trip to keep something like that organic. I can’t hacky sack like the way you saw that sequence cut together—I have 5, 6 reps in me tops. I had to have an earpiece in my ear that kept this weird, modern art-crappy beat in my head, and do the hacky sack, and even if it fell, I had to continue the sequence: “Never let it drop… don’t let it drop… sooner or later, it has to drop.” I can’t believe I remember those lines! They brought in this world-class hacky sack player who had tricks like nothing I’d ever seen, and in 5 minutes he had me going from 6 in a row to 12 in a row.
Rachael Leigh Cook: All of my concern about that scene was related to the leotard. I had no content complaints about that scene, I was entirely focused on what I was going to look like in a unitard, because who wouldn’t? Well, unless you’re Paul Walker. [Laughs]
Robert Iscove: Lee Fleming had a great knack for linking the script to the past, so Laney Boggs is named after [Winona Ryder’s character] Kim Boggs in Edward Scissorhands and Laney Pierce in Reality Bites. And the Zack and Taylor characters are named after the members of Hanson. But Lee Fleming was so good at these character’s vernacular that after M. Night did his rewrite, I brought Lee Fleming back on the movie to rewrite all the things M. Night had done in Lee Fleming’s voice.
REMEMBERING PAUL WALKER
Robert Iscove: Richard Gladstein, who was one of the producers, knew Paul from Meet the Deedles and brought him in to have a meeting with us. Paul was very reluctant to do the movie. He joked, “You don’t want the second banana to be better looking than your lead guy.” [Laughs] He was anxious to show both his dramatic chops, and his comedy. He was a sweetheart, you know.
Freddie Prinze Jr.: Everyone wanted to be Paul Walker’s character. People would come up to me and go, “Yeah, your character was cool and all, but I want to be like Paul Walker’s character.” Everyone always wants to be all big and buff, right? [Laughs]
Rachael Leigh Cook: Paul seemed like a big deal even then. I think we knew that he had been cast in Varsity Blues, and he was in Pleasantville, which was THE movie that you wanted to be in if you were roughly all of our ages at that time. I went in to audition for it [for the Reese Witherspoon part] and I’m pretty sure the rest of our cast did, too.
Freddie Prinze Jr.: Paul and I, we didn’t have much of a relationship when the film was over, but we had a relationship on the film. When he came in and read, it was him against this other actor, and Paul was the less famous of the two, and he did a great job on the audition. Back then, an actor would have to wait 2-3 weeks to be told whether they got the part and that was just bullshit. So after I knew he got it, I left the room, saw him in the parking lot and told him, “Look, you got it. Don’t tell anyone I told you, and make sure you don’t accept scale. They want you, not the other guy.” And he froze and was like, “Dude, are you serious? Thanks so much for telling me!” And they didn’t end up telling him for two more weeks! So we were really cool all throughout the shoot. Plus, he was big into jujitsu like me. It’s a respectful, spiritual vibe, if you’re into jujitsu. But we never got to roll [in jujitsu] once! I wish we had.
CHERISHED MEMORIES FROM SHOOTING
Tim Matheson: We shot near Ronald Reagan's Bel Air home, the Western White House. He had settled in after his terms of office were over.
Freddie Prinze Jr.: The dance sequence is the best for a thousand reasons. That’s the scene where I met Adam Shankman [the choreographer], and he became my friend and my wife’s friend. When it came time to marry us, we got Adam ordained online so he became “The Holy Reverend Jewish Dude Adam Shankman,” and married us. And it’s a sequence that I was horrified to do, because I had never danced on camera before. I was more in the Fat Joe world of, “Gangsters don’t dance, we just pull up our pants,” but Adam made it very simple and showed me the crew, and the dancers were just killer. I remember Dulé being pissed that he wasn’t able to tap dance, so he insisted on doing this stupid hoedown thing.
Robert Iscove: I’m sorry I couldn’t get a tap number in the movie from Dulé!
Freddie Prinze Jr.: Dulé’s this world-class tap-dancer. 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. Eventually, I turned a room in my house into a tap dance studio and we’d put on rap music, tap dance, and drink scotch until like 4 in the morning. Dulé Hill is a great friend. He was in my wedding and he’s held my children.
Rachael Leigh Cook: I remember seeing Dulé tap dance! For the big dance number, I was trying to protect myself so I remember making the case to our choreographer, Adam Shankman, that my character wouldn’t know this dance and that I’m not a born dancer, so I think that’s how I ended up just doing a move or two here or there. Jodi’s character did most of the dirty work. And if I ever hear “The Rockafeller Skank” again I’m going to shoot myself. [Laughs]
Jodi Lynn O’Keefe: My favorite memory of the entire shoot was the dance scene, and the night we actually had to film it. We were all in our prom gowns and tuxedos, and I laughed my face off. The number of times I fell on my face was crazy. Usher was DJing the entire thing, too. I look back on it now and I’m like, “Oh my god! Usher was our high school DJ?” That kills me.
Usher: The prom scene was the most eventful for me. I was able to live my high school prom experience through filming because I wasn't able to attend my own prom.
Rachael Leigh Cook: No one was as cool as Usher, and I was a huge Usher fan, so one of my most cherished moments from filming was when I walked up to the set to shoot the prom scene—having missed my own prom, and much of the “normal” high school experience because of acting—and meeting Usher and him saying, “Hey, pretty girl!” I thought to myself, “Make sure he’s talking about you before you say anything,” so I really looked around, but we were in a parking lot at the time so it was definitely to me. I remember being very bashful at the time and saying, “Thank you!” He really made my day, that’s for sure.
HARVEY WEINSTEIN’S STAMP
Robert Iscove: Harvey wanted to cut the big dance number! We fought forever about the dance number and it wasn’t until Harvey said, “OK, I’m going to get Usher to do more scenes and all that then,” that he gave in. Harvey didn’t understand why you’d stop the movie for a big dance number. I had seen some stuff that Adam Shankman had done—a video he did—and knew that the style was exactly right for it.
Freddie Prinze Jr.: Harvey wanted to put a sword fight in this movie for no reason whatsoever! “It’ll be from the drama department, and they’ll be this sword fight, and it’ll be great!” We were like, “That’s not even in the script!” And then his brother, Bob, comes in and goes, “Yeah, it’ll be great.” But they were worried about the dance sequence? Come on, man! And then, me and Rob did this other movie, Boys and Girls, and we got a note from Harvey that said they wanted to put a sword fight into that one, too, which made no sense because it was a contemporary piece, and Jason Biggs played an architecture student! Those were the crazy notes you’d get from the studio back in the day. I don’t understand how Miramax directors didn’t all go insane.
Rachael Leigh Cook: Oh. My. God. I would’ve been up for fencing, though! That’s an amazing piece of trivia.
Robert Iscove: They didn’t understand why Kieran’s character had hearing aids and wanted more resolution, and I didn’t think we had to go into that. Paul’s character went dark and they were iffy on that transition, but the movie had to have a villain. And with the party scenes, they didn’t want kids drinking alcohol at the party, which is common in most movies. I told them, “Well, if you want them just drinking water then it’s a drug party.” The studio also had issues with the pubic-haired pizza scene. They didn’t know if it was right for kids and they wanted to keep the PG-13 rating. There were hours of conversations about, “Well, how many corn stalks do we put on the pizza? Has he torn out all of his pubes, or only a couple of pubes?” But now it’s one of those great, groan-worthy moments. But Harvey left us alone pretty much during shooting and came in two weeks into the editing process and said, “OK, I think we really have something here. I’m going to put $18 million into TV ads.” I said, “If I had half of that to make the movie, that would have been great!” But I was kidding.
Freddie Prinze Jr.: They released the film on the day my father took his life, and that day, January 28, was a hardcore thing for me to process and deal with at that time in my life. I remember speaking to Kevin Pollak at the time and said, “I don’t think I can go to this premiere, man. I’m freaking out.” And his wife at the time, Lucy, calmed me down to the point where I could get in the car and go there. I had crazy visions like something bad was going to happen. But I got there and everyone seemed to enjoy it. I’ve only seen the film once and it was in that weird frame of mind, so I’ve never really gotten the opportunity to properly appreciate it. Hearing Harvey Weinstein go, “I don’t care if your father died today! You’re going to the premiere of the movie!” which was what they were feeding me, was hardcore.
Robert Iscove: Those kids made up that freestyle rap scene! We were setting up the scene with Laney in the courtyard and they were extras just standing around and rapping it, “Ba-dum… She’s All That!” They’d just made it up on the spot, and we were like, “This has to be in the movie.”
Rachael Leigh Cook: When we were shooting that infamous scene of, “Am I a bet? Am I a fucking bet?” it really resonated with Freddie somehow, and he would really cry after every take. I remember when the director said, “Cut,” he’d be tearing up. It rocked him a bit. I remember thinking he was such a stellar person for having that reaction to a scene.
Freddie Prinze Jr.: I remember we were shooting the volleyball sequence and Dulé was doing really well and getting these good vertical jumps and spikes, and Rob was just getting these montage shots. Behind him, I had dug “Dulé Sucks!” in big vertical letters with my foot, and I didn’t know Rob couldn’t see it. Two days later, Iscove came up to me and was like, “What the fuck?” And I was like, “What?” And he said, “I just saw the dailies from the beach! It’s unusable! The whole sequence now has ‘Dulé Sucks’ in the background!” I don’t think those scenes made it into the movie.
Robert Iscove: I would say about half of Matt Lillard’s dance during the “Give It to Me Baby” sequence was improvised. He was great.
Matthew Lillard: I WISH that were true. If I could do that off the cuff I would be WAAY more fun at parties! I worked with the incredible Adam Shankman and his assistant at the time Anne “Momma” Fletcher. We worked for three days to put it together… every time I hear the song I feel the slightest tinge of rhythm rollin’ through my loins.
Rachael Leigh Cook: He just went for it. I think Matthew, in retrospect, had the clearest idea of what this film was going to be, because he really pushed the limits of the tongue-in-cheek aspect of it. I’m really happy that he did because he’s one of my favorite characters in the movie. I also loved the whole Real World show-within-a-movie thing. I thought that was inspired.
Robert Iscove: Lee had started some of the Jeopardy things in the script, but a lot of the stuff Kevin came up with. He’d just sit in his dressing room and go, “How about this one?” and “How about this one?” It became a much bigger part of the film because of Kevin.
Kevin Pollak: After getting a few takes on the scene when I'm giving answers to the TV as I watch Jeopardy, I was asked if I wanted to improvise my answers for comedic effect. So, when I watched that scene at the premiere and saw that the director chose only the answers that I made up, I was surprised and delighted beyond belief.
Jodi Lynn O’Keefe: “You’re vapor, you’re SPAM, you’re a waste of perfectly good yearbook space!” I can’t believe I remember that from 15 years ago! That dig was written that way, though. My character was really well written. She was terrible to her core, and great.
Robert Iscove: Harvey put Lil Kim in the movie. I had not known about her rap career prior to shooting, and it wasn’t until the end of the shoot that she gave me all her discs. I thought, “Thank god I didn’t know about this before,” because I only knew her as this sweet young thing that she was presenting in the film.
Freddie Prinze Jr.: This movie cost us $6 million to make. It was not a big budget film. Lil Kim showed up in a stretch limousine to the set and was wearing almost our budget in diamond earrings, rings, necklaces, sunglasses, high-heeled shoes with diamonds on top. I remember thinking, “This girl’s got like $3.5 million on her right now!” And that’s how she came to the set every day. I remember thinking, “I wish I had some rap talent!”
Rachael Leigh Cook: I can’t believe that? Three million? I’m not surprised. I’m really upset that I never saw that! I do have some Polaroid’s of Freddie and I wearing Kim’s wigs in the make up trailer when she wasn’t around. He looks fantastic. But I ran into Lil Kim about five years after the movie was done and she looked so different I didn’t recognize her at first, and then I heard her voice and realized it was her, and she was just as nice as could be.
Jodi Lynn O’Keefe: I actually kept in touch with Lil Kim for a while after!
Freddie Prinze Jr.: People tell me, “Hey, I loved that movie!” and sometimes girls come up and go, “You were so cute back then!” and then quickly try to qualify it, like, “Oh, but you still are!”
Rachael Leigh Cook: After I got the message that you wanted to chat, I asked for Freddie’s managers info because I haven’t talked to that guy in over a decade, and he’s the nicest, coolest, funniest person. I guess we don’t run in the same circles but I’m going to call him up and hunt him down. And I always feel like I’m on Candid Camera when I’m in the drug store or something and “Kiss Me” comes on, because I think it subliminally triggers memories from the movie for people, so then you get the, “Do I know you from somewhere?” from the cashier. The fact that I still bear a passing resemblance to that girl from 15 years ago makes me happy.
Robert Iscove: It was the biggest opening in Miramax’s history up to that point! We had to trust Harvey’s marketing skill and he said, “Super Bowl weekend’s the weekend to open it,” and he proved to be right. I was at the openings in France and in Rome, where it was called Kiss Me—in English. It amazed me because they don’t have that high school experience, they don’t have proms, and the film really resonated well in those countries. It shocked me that this little film we made in Torrance, California, connected with people abroad.
Kevin Pollak: When I finally met Freddie on the set I told him that I was there because of my seeing him in House Of Yes, and my sincerity and fandom made him tear up a bit. Turns out he had been a fan of my stand-up comedy since he was 12 years old, as he explained, and when I heard that I told him how much his dad meant to me and we became fast friends, which I'm quite pleased to say remains to this day.
Jodi Lynn O’Keefe: I run into pretty much everyone from time to time. I recently ran into Freddie at the grocery store, which was so weird because we hadn’t seen each other in years, and he actually ended up marrying my childhood friend, Sarah Michelle Gellar. We were friends when we were 8 and met while doing kids modeling for the Ford Agency in New York. We were on the same cover of a couple of children’s books at the same time, like Sweet Valley High. We go way back.
Matthew Lillard: It’s a quintessential 90’s teeny-pop film. There’s an innocence about those types of films that people can hold onto.
Usher: I feel like I was a part of a legacy, it was like The Breakfast Club or Ferris Bueller's Day Off of that era. I'm happy I did it.
Freddie Prinze Jr.: I fell asleep on the couch at like 11:30 pm watching Some Kind of Wonderful. I’d just finished doing Wing Commander in Luxembourg, and that flight was brutal, so I closed all the curtains in my house and passed out. And when I woke up, it was only like 11 minutes later in the movie. I was like, “What?” I’d literally slept for 12 hours straight and the movie had just come on TV again on a Cinemax loop. I’d just gotten She’s All That, and I had this weird vibe that it would be that sorta vibe. Some Kind of Wonderful was never going to be The Breakfast Club, because that’s this beautiful play that somehow works as a movie, but it was still a movie that reached out to the jocks and the outcasts, and if She’s All That could be like Some Kind of Wonderful, I thought that would be great, because it’s more for the outcasts. When our movie first came out, a lot of people went teenybopper crazy, but a lot of people also came out and said, “That was me, man.”