In regards to teen films, the class of 1999 is a pretty elite group. That year we got 10 Things I Hate About You, Cruel Intentions and American Pie to name a few but arriving second that year was She’s All That, one of the first of the 90s teen romantic comedies to find great success at the box office. The film was released on January 29, 1999, and opened two weeks after Varsity Blues, another teen film that seized the top of the box office for two weekends in a row.

For She’s All That, the timing was everything and the reason it still resonates today is that it has a lot of heart and charm, despite swimming in cliches of the genre.

The transformation of the ugly duckling has its roots in George Bernard Shaw’s Pygmalion and its most famous movie incarnation, My Fair Lady. Somewhere along the way, this became the foundation for nearly every teen romantic comedy at the time She’s All That was released (except Clueless, which took the Emma route). 1987’s Can’t Buy Me Love is probably one of the best examples from that time period and She’s All That would become the most significant one to take on that premise when it was released in 1999. You take someone, usually the girl, who is a bit nerdy but still pretty by just about anyone’s standards and pair them with someone good looking and popular and it’s their goal to turn the ugly duckling into a swan. There’s usually some kind of ulterior motive that sets this into motion. In the case of She’s All That it involves Zack Siler (Freddie Prinze Jr.) who is the most popular guy in school and a shoo-in for prom king. Not only is he good-looking but he’s got the fourth-highest GPA in his class and has been accepted to every college he has applied to. The girl who becomes his makeover goal is Laney Boggs (Rachael Leigh Cook), an unkempt art student with minimal social skills and is “a waste of perfectly good yearbook space” as Zack’s ex-girlfriend Taylor (Jodi Lyn O’Keefe) puts it. Zack and Taylor were an item until she came back from spring break and broke up with Zack because she met Brock Hudson (Matthew Lillard), a self-centered TV star who was on The Real World. It’s this event that prompts Zack to accept a bet put in place by his friend Dean (Paul Walker).  Zack consoles himself by claiming that Taylor is replaceable by any girl in the school.  Dean disagrees and challenges him to a bet on whether Zack can turn any random girl into the Prom Queen within six weeks, a coveted position held by the most popular girl in school. Thus the genesis of She’s All That is born.

Even though all of this has been done before and even a mere month and some change later after the release of She’s All That in 10 Things I Hate About You, the film doesn’t succumb to all of its familiar cliches because of the appeal of its characters. Zack is likable and charming while Laney is adorable and worth rooting for. Freddie Prinze Jr. and  Rachael Leigh Cook share solid chemistry and even though R. Lee Fleming Jr.’s script isn’t high art, they deliver some of his zingers with enough talent and screen presence to make it all work. The charm even extends to the supporting cast which includes the late Paul Walker, Jodi Lyn O’Keefe, Matthew Lillard, Anna Paquin, Kieran Culkin, Gabrielle Union, and Dule Hill. They may be filling in typical teen movie stereotypes but they’re having fun with the material and it’s clear that they are enjoying themselves.

Surprisingly, She’s All That has aged pretty well. There are the usual signs of its 1999 birth but the themes and concepts still ring true and you can see a lot of what She’s All That does in teen offerings today. It also, like any film that breaks the pop culture barrier, has been referenced, imitated and made fun of in various other projects. Its most iconic moments are referenced in everything from then-contemporary films like Jay and Silent Bob Strike Back and Not Another Teen Movie (which famously parodied most teen movies of 1999), to more recent TV shows like Scream Queens, Superstore, Brooklyn Nine-Nine, Broad City, and The Unbreakable Kimmy Schmidt. I even learned in some of my research that the new series Schooled just aired a She’s All That inspired episode just last week. I mean looking back at it, doesn’t the infamous “Rockafeller Skank” prom dance sequence seem more like the viral moments that fuel the internet today as they are shared by people all over the world? It really seems like She’s All That was ahead of its time in a lot of ways.

She’s All That wasn’t really embraced by critics (it carries a 40% rotten rating on Rotten Tomatoes) with some critics calling it “formulaic, toothless — adolescent, in the worst sense of the word.” The fact of the matter is, She’s All That wasn’t made for the critics. It was made for its target audience and at the time it became one of the most popular teen films of the 90s. It claimed the number one spot at the box office from Varsity Blues, which spent two weeks at the top spot before She’s All That came along and ultimately grossed $63.3 million domestically and $103.1 million worldwide, all on a $10 million budget.

At the end of the day, there is a message in She’s All That. Sure, it’s a cheesy teen film from the 90s but even 20 years later, its resolution is something that should still be taught to kids who are currently navigating the halls of high school. It’s really a story about being yourself and although Zack tries to change Laney, it’s Zack who realizes he has to make changes in order to win over a girl who’s out of his league intellectually and emotionally. From a pop culture standpoint, She’s All That has an impact that is obvious. Teen movies come in waves. Nearly two decades after She’s All That, 2018 gave us a whole new slew of high school heroes to root for: Love, Simon broke barriers by showcasing a gay love story in an otherwise textbook teen rom-com; Blockers proved that young women could own their sexuality without permission from the men around them & The Hate U Give put the life and death concerns of Black teens front and center. I haven’t seen it myself but I hear that To All The Boys I’ve Loved Before revitalized the genre with a fresh, insightful look at what it means to be a teenage girl. All of these films owe a debt to movies like She’s All That because 20 years later, the formula is familiar but constantly being revamped for a new audience. Besides, even if you don’t want to look into the deeper side of the film, you can still just enjoy the prom dance sequence and listen to the sweet sounds of Sixpence None The Richer and soak in all of the nostalgia.

Check out a few 20th anniversary facts about She’s All That below:

1. Filmed at the same high school as Buffy The Vampire Slayer. Sarah Michelle Gellar, who was the star of Buffy at the time, has a small non-speaking cameo in the film and also co-starred with Freddie Prinze Jr. in I Know What You Did Last Summer in 1997. The two would later get married and are still married today.
2. The Prom dancing sequence originally wasn’t scripted and wasn’t going to be filmed. It was added in at the last minute to make the movie go a few extra minutes. The sequence was choreographed by Adam Shankman, who would go on to direct A Walk To Remeber and Hairspray.
3. This film was the last to be reviewed in print by Gene Siskel before his death. The famous critic os Siskel & Ebert fame actually gave it a favorable review.
4. It was the film debut of Gabrielle Union.
5. In a 2013 interview,  M. Night Shyamalan claimed to have ghostwritten the script. Fleming has denied this. On the Blu-ray commentary for the film, director Robert Iscove confirms that Shyamalan was brought in after pre-production began as a contributor to the script. After his story points were added, the final rewrite was then handed back to Fleming so that he could lend the story his unique voice in writing for teenage characters.
6. Freddie Prinze Jr. and Matthew Lillard appeared together again in the Scooby-Doo movies, as Fred and Shaggy.
7. Director Robert Iscove said in a 2014 interview that Josh Hartnett was considered for the role of Zack before Freddie Prinze Jr. was cast.
8. Dule Hill (Preston) and Rachael Leigh Cook (Laney Boggs) later appeared together in the 2006 series, Psych, as Burton ‘Gus’ Guster and Abigail Lytar, respectively.
9. The falafel restaurant is the same one used in the 1989 movie Loverboy starring Patrick Dempsey.
10. Milo Ventimiglia is one of the JV soccer players cleaning the house in one of the scenes.