Along with Napster, Harry Potter and Y2K panic, teen rom-coms were all the rage in 1999. 

It's unclear if a certain sect of screenwriters got together and agreed that the waning years of the millennium were the time to churn out delightful fare for the underage set, but between 10 Things I Hate About You, Varsity Blues, Cruel Intentions and She's All That it was quite the time to be in high school and dreaming wistfully of first loves and perfect prom dates.

Albeit somewhat disturbing to realize that a bespectacled Rachael Leigh Cook and a poorly attired Drew Barrymore are what pass for impossibly nerdy in Hollywood. 

Such was the premise for Never Been Kissed. Barrymore's Josie Geller is the youngest editor at the Chicago Sun-Times with a penchant for correcting her colleagues' grammar (which, respect), but, perhaps, not yet possessing all of the skills necessary to land the reporting job of her dreams. Then, apropos of nothing, her editor-in-chief instructs her to go undercover at nearby South Glen South and write about her semester in high school.  

The only issue? Josie didn't exactly have the strongest social game as a teen the first time around. And while she totally has been kissed, she's the type of hopeless romantic that believes she should only be puckering up for "the person you're supposed to kiss for the rest of your life." So basically she's totally going to kill it with her fellow youths. 

Dressed in an unfortunate feather boa-lined all-white ensemble, Josie quickly befriends brainy Aldys (Leelee Sobieski), an aspiring professor, novelist and flautist who's already figured out that her best years lie ahead, and develops a troubling crush on Cool Teacher Sam Coulson (Michael Vartan). But with prom fast approaching, hanging with the math club (appropriately named the Denominators) and lusting over an English instructor with boundary issues is not going to get Josie the story she's after. 

For that she relies on brother Rob (David Arquette), also going undercover, to gain her entrée into the cool kids group, which includes a pre-stardom James Franco and Jessica Alba. 

With Rob vouching for her—perhaps the truest line uttered in the movie is when he tells Josie, "All you need is for one person to think you're cool, and you're in. Everyone else will be scared to question it"—she scores a popular date to the big dance, the title of queen and the chance to finally yell out, "I'm not Josie Grossie anymore!"

We're not saying the movie is without its troubling moments. The so-called dream guy, whose name is actually Guy (Jeremy Jordan), refers to unpopular girls as "dogs," and the school clearly has very lax admission standards. But the overarching message about how it's cool to be yourself is sweet. And the whole teacher falling for a student storyline is made more palatable by the winning charms of Michael Vartan. 

By the end, after Josie has apologized for duping him and asked for a shot at a legitimate relationship with all the trappings of a rom-com, who wasn't rooting for Mr. Coulson to show up at the packed baseball stadium and just kiss her already? 

Released 25 years ago on April 9, 1999, Never Been Kissed served as a vehicle for more than a couple legitimate Hollywood careers (hi, Academy Award-winner Octavia Spencer!) and boasts quite a few behind-the-scenes tidbits you've likely forgotten in the past two-plus decades. 

1. The rom-com was the first production for Drew Barrymore and Nancy Juvonen's Flower Films. "I wanted to make this movie because it taps into an emotion that everyone can identify with—the awkward moments of our high school years," the actress told Wild About Movies in 1999.

Coming off her work in Ever After and The Wedding Singer, it was a marked success for the former child star and led to a slew of other successful work. (See: 50 First Dates, He's Just Not That Into You, Whip It!)  "I had fun but wanted to make it work," she told E! News of her first producing gig, "and then when it did I was allowed to make Charlie's Angels so each movie is a piece."

2. Just three months before selling the script, screenwriting partners Marc Silverstein and Abby Kohn were master's degree candidates at University of Southern California. And their stellar first project launched a romantic comedy career for the ages.

After some TV work, they re-teamed with Flower Films for 2009's He's Just Not That Into You before diving into Valentine's Day, The Vow and How to Be Single. "We ride the wave and you just push it around into different areas," he told ET. "We moved into the romantic drama, we moved into the multi-character story arc version of that movie. You just try to keep it fresh. People want to see stories about relationships."

3. Before Silverstein would go on to meet future wife Busy Philipps (the pair announced their sepration in 2022), he and Kohn were a thing for some seven years, breaking off an engagement in the early aughts. "When we decided not to get married, we were contractually obligated on a pilot," Silverstein told the Los Angeles Times. "So we figured we should try to work together."

It wasn't great, they agree, "but it didn't take that long to get normal again." Kohn would go on to wed music exec Jason Linn and Silverstein married Philipps and now, he said, "I think we have the best of both worlds. I know a lot of writing teams that, as good friends as they are, still can't say to each other what we can say to each other." 

4. James Franco was perhaps a little hard to spot in his debut film role of cool kid Jason, which saw the UCLA student (credited as James Edward Franco) offer up a scant few lines and mostly serve as a background player in prom-perfect disco attire.

Before the comedy, Franco's credits were limited to a TV movie and a guest spot on Pacific Blue, but later that year he'd break out as head freak Daniel Desario in Freaks and Geeks alongside Silverstein's future bride Busy Philipps.

5. The teen fare also featured a little-known 17-year-old Jessica Alba, a year away from landing on TV screens in Dark Angel. Though she was spot-on as cool kid Kirsten, Alba has admitted she had very little to draw on. "I actually never went to high school. I graduated when I was sixteen," she said of her stint at an L.A.-area academy, "but when I was in junior high, I was, like, the biggest nerd and I had no friends."

Once she began acting—including a two-season gig on Flipper, "They wanted to be my friends, then they wanted to beat me up because I was in magazines and stuff," she continued, "but yeah it brings back weird issues."

6. Supporting leads Barrymore and Michael Vartan was a wealth of talent in secondary roles. All told, the film can claim their cast was made up of three Emmy-nominated actors (Barrymore, Leelee Sobieski and Molly Shannon, who nailed her part as Josie's work BFF), two Oscar nominees (Franco and John C. Reilly—Josie's grumpy boss Augustus in the flick) and an Academy Award winner in Octavia Spencer, underutilized in a bit part as one of Josie's coworkers. 

7. Jeremy Jordan had some experience to draw on playing Guy, the high school heartthrob you totally want to be crunched by. In a bid for pop star fame, he released his debut disc, Try My Love in 1993, with his two biggest hits, "The Right Kind of Love" and "Wanna Girl," peaking at 14 and 28, respectively, on the Billboard Hot 100. Though his acting credits were limited post-Never Been Kissed, he did put out another album in 2013 titled Where Do We Go From Here.

8. One of the bigger stars in the film thanks to her work in Deep Impact and A Soldier's Daughter Never Cries, Sobieski was reportedly offered popular Kirsten, before saying she found the role of ambitious Aldys more interesting.

She'd continue racking up parts before telling Vogue in 2012 that she was looking to retire in deference to her marriage to fashion designer Adam Kimmel: "Ninety percent of acting roles involve so much sexual stuff with other people, and I don't want to do that. It's such a strange fire to play with, and our relationship is surely strong enough to handle it, but if you're going to walk through fire, there has to be something incredible on the other side."

9. Meanwhile, Vartan almost missed out entirely. "I auditioned for Never Been Kissed 116 years ago and I was as nervous as can be," he told E! News during a 2017 visit to The Arrangement's set. "It was my first, one of my first really big movie auditions and I really had no notion or thought that I was gonna get the job."

He credits screen partner and producer Barrymore with helping him score the role of far-too-dreamy teacher Mr. Coulson saying, she "fought very hard for me and I got the job."

10. As if Vartan wasn't charmed enough by Barrymore, her arrival on set certainly sealed the deal. Though the former child actress was already a bonafide star many times over (not to mention the boss, with her Flower Films helming production), "The first day she showed up on that job, she showed up in a 1970s beat-up white Volvo," Vartan told Bravo's The Daily Dish in 2018, "and I was like, 'I like that girl. [She's] down-to-earth, salt-of-the-earth. No nonsense with her. [She's] just a real sweet person."

11. Costume designer Mona May revealed Barrymore got very hands-on choosing Josie's eccentric fashions for the film. (Never forget the all-white, boa-tinged outfit with an accompanying citrus-themed tote.) "We went to Loehmanns to try clothes on because she really wanted to find the coolest, weirdest stuff to create this character," May told Interview in 2018. "She's so strong in her visuals and how she likes things, so it was really us creating it together, which is always really fun."

By the credits, Josie has undergone more than an internal evolution. "At the end we clean her up and you find her soul," said May. "She's gone through this crazy journey and she's now who she's supposed to be."

12. In the decades since that first release, Barrymore and May have gone on more than one department store adventure. "I've worked with her for many years," May raved to Interview of dressing the actress, including for Barrymore's Netflix series, the Flower Films-produced Santa Clarita Diet. 

13. With a peak nineties soundtrack, the film secured the rights to choice songs by Jimmy Eat World, Cyndi Lauper, Blind Melon, Pat Benatar, Madonna and Big Bad Voodoo Daddy. But one standout moment comes when Josie discovers that the more charming parts of South Glenn South's student body have pushed her car into the middle of the football field. The number the marching band is practicing at that moment: The theme song for The Simpsons. 

14. Even legendarily tough film critic Roger Ebert was won over by Barrymore's charms. Though he goes in on the screenplay a bit (it's "not deep or sophisticated, but it's funny and big-hearted and it wins us over"), he admitted he found himself cheering for the requisite happy ending. "The scene is so contrived and artificial, it could be subtitled 'Shameless Audience Manipulation,'" he wrote in his 1999 review. "But you know what? Because the wait involved Barrymore, I actually cared. Yes, I did." 

15. Despite the use of the very legitimate Chicago Sun-Times and various necessary exteriors in the Windy City, the movie was largely shot on location in Los Angeles.

John Burroughs Middle School filled in for South Glen South, UCLA's Jackie Robinson Stadium served as the backdrop for the all-important finale and Josie's childhood home was actually located in the city's Hancock Park neighborhood. As for The Tiki Post, where Rob toiled before his dreams of a baseball career could take off, it's now a Cold Stone Creamery in Monrovia, Calif. 

16. As a clichéd editor-in-chief with nary a trace of subtly, Garry Marshall remarks in one conference room scene, "I don't even know my own kids." Sitting directly to his right: real life daughter Kathleen Marshall, whose other credits include Happy Days, Laverne & Shirley, Runaway Bride and The Princess Diaries.

17. To promote the April 2019 premiere of the flick, Barrymore turned up on Saturday Night Live, her second of six hosting gigs and her first since her debut at age 7 made her the youngest lead ever.

And, yes, there was some kissing. "That was the best thing ever," the actress told Wild About Movies of returning to the sketch comedy show. "But kissing Molly Shannon was even better." Her costar agreed, telling the outlet that Barrymore had skills: "We even did some kissing during our dress rehearsal." 

18. Though there's no chatter of a reprisal for the 1999 flick, screenwriters Kohn and Silverstein say it did serve as inspiration of sort for 2018's I Feel Pretty, starring Amy Schumer as a cosmetics employee who gets the self-confidence knocked into her after falling off a SoulCycle bike.

Asked how their approach for that comedy varied from their first, Silverstein told ET, "Between this and Never Been Kissed, not that different at all. When we started this, we felt like this is a spiritual successor to that movie in a way. Because, again, it's a lead character comedy that has a broad, high concept to it, but it's treated in a very real way."

19. For the record, though, if there were to be a reprisal, count Vartan among those who believe Josie and Sam are still holding steady. "Well, I mean, I think we'd be age appropriate, at least," he told Bravo's The Daily Dish last year. (At 24, Barrymore was just a year younger than her character while Vartan was 30.)

"I mean, she's still younger than me, but yeah maybe I'd be the janitor and she'd be the principal of the school. I guess I'd still be a teacher. Maybe I'd have a tie now, like a little cloth tie. I have no idea."

20. Despite a bevy of roles to choose from, Barrymore names Never Been Kissed as one of her "favorite films" from her storied four-decade career, telling UK's Glamour she "loved playing Josie."

The experience is edged out just slightly by 1998's Ever After, a riff on the classic Cinderella fairytale because the decidedly feminist retelling of the story taught Barrymore how to "rescue" herself. No wonder, then, that the actress would be down to reconnect with her former costars. "We need to do something—a reunion," she told E! News ahead of the 20th anniversary. "We loved it and each other."

(Originally published Tuesday, April 9, 2019, at 3 a.m. PT)