How Well Does ‘Never Been Kissed’ Hold Up 20 Years Later?

On this day twenty years ago—April 9, 1999—a little film called Never Been Kissed hit theaters. It did well in the box office, though not a smash hit (that was the year of The Phantom Menace and The Sixth Sense, after all). Critics were lukewarm on it—this was the golden era of teen rom-coms like Clueless, 10 Things I Hate About You and She’s All That and the consensus was that Never Been Kissed, which starred Drew Barrymore as a 25-year-old reporter who poses as a high school student for a story, didn’t have much new to offer.

Then came the dry years of the rom-com, and lovers of the genre were starved for content. Never Been Kissed, written by Abby Kohn and Marc Silverstein and directed by Raja Gosnell, was suddenly a precious gem in a sea of antiheroes and war movies, and was fondly remembered as one of the greatest romantic comedies of all time. (Seriously, Google it!)

But here’s the thing: Twenty years is a long time ago. Times change, humor changes and whether it’s socially acceptable for teachers to hit on students changes. That said, Barrymore’s charm is timeless and Molly Shannon is forever. So the question is: Twenty years later, does Never Been Kissed hold up? I decided to dig into it.

The Premise

Alright, so Never Been Kissed centers on Josie Geller (Barrymore), a 25-year-old copy editor for the Chicago Sun-Times. Josie’s obsessed with order, corrects everyone’s grammar, and waxes poetic about meeting the man of her drams—love all that so far. Josie, who is again a 25-year-old copy editor, also inexplicably has her own office with her name on the door—less excited about this, but I’ll let it pass.

One day, the cartoonishly cut-throat Chicago Sun-Times editor, played hilariously by renowned film director Garry Marshall, decides it’s time to get to the bottom of what’s really going on with teenagers these days. Fine. The way to do this, he decides, is to send his youngest employee—that’s Josie—back to high school for a months-long investigation. Then all the other reporters sit around in the newsroom and watch Josie’s adventures on a hidden camera, á la The Truman Show, a film that came out the year prior. Then later, for very, very loose reasons, her brother also enrolls in that same high school. It’s truly all over the place.

This is where the film loses me. Look, I know journalism was a booming industry in the 90s compared to the deserted wasteland it is today, but surely no editor in their right mind would choose this course of action when you could just, hear me out, interview some high schoolers. 

I know, I know, it’s a movie! They just needed to get Drew Barrymore back to high school! But I could have used more than a 30-second scene of Garry Marshall shouting about how his son has a peanut allergy to justify this one, is all I’m saying.

The Verdict: Does not hold up!

The Jokes

Comedy is a key part of a solid romantic comedy (it’s right there in the name, after all) and Never Been Kissed has a great cast for it: In addition to Barrymore, Marshall, and Shannon, you’ve also got David Arquette (as Josie’s brother Rob), John C. Reilly (as Josie’s boss), Octavia Spencer (as Josie’s coworker), Jessica Alba (as a popular high school girl), James Franco (as a popular high school boy) and more.

I’m happy to report that Never Been Kissed makes good use of this cast. The jokes are solid! I laughed every time the entire school went dead silent to listen to prom announcements. Drew Barrymore is charming and delightful. James Franco declares that an upcoming concert is going to be “ruf-i-licious,” which is supposedly a hip new teen phrase that he’s misusing. Molly Shannon poses as a sex-ed teacher, and starts her lecture by saying: “You like a guy, you do it with him, sometimes he calls, and sometimes he doesn’t!” It’s great!

The Verdict: Holds up!

The Montages

You gotta love a montage (montage), and by my count this movie has three of them: One for when Josie is becoming a nerd with The Denominators, one for when her brother is talking her up, and one for when she’s becoming a popular girl. All are incredible, but The Denominators montage is particularly delightful, even if the poster for the Pi Day sale only gets the first three digits of Pi correct.

The Verdict: Holds up!

Drew Barrymore’s Dancing

Incredible. Inspired. Visionary. I have nothing more to say on this matter. I’ll let the GIFs speak for themselves.

The Verdict: Absolutely holds up!

The Romance

Ah, the big sticking point of this film: The romance between Josie and her teacher, Mr. Coulson (played by Micheal Vartan). No, Josie is not really a 17-year-old high school student. Yes, Mr. Coulson does think that she is. No, that does not stop him from hitting on her.

Here are some facts about Mr. Coulson, as presented to us in Never Been Kissed: Mr. Coulson goes out to party at the local student hangout spot on weeknights. He feels held back by his nagging girlfriend, who would rather do boring adult things like go to a museum rather than hang out with teenagers (the nerve!). He’s clearly instantly attracted to Josie, and comments that 17-year-olds don’t usually know things like Shakespeare, which suggests he was only previously held back from feeling attraction to 17-year-olds because they weren’t up on their literary references. He joins Josie on a romantic Ferris wheel ride, talks to her about his relationship problems, tells her she’s beautiful, asks her to dance at the school prom, all while thinking she is 17. That’s a big no from me on Mr. Coulson!

Here’s the best part: When Mr. Coulson discovers that Josie is in fact, not 17, instead of doing some soul searching on how he probably has a boundary problem with his students, he instead yells at Josie for being a liar and storms off. That’s right: He gets pissed at her, for not being a high school student. Sorry to burst your bubble, Mr. Coulson, turns out you weren’t about to have a sexy affair with an underage student after all. I know, it’s a real bummer. (Side note: Both Josie and her brother also take high school dates to the prom, which is also not cool!)

I’ll say this: The best part of this film is when John C. Reilly suggests the real story here is that Mr. Coulson is totally into his students. I really wish that Josie had published that story, rather than her heartfelt love letter apologizing to Mr. Creepy.

The Verdict: Really does not hold up!

The Ending

In the end, Josie confesses in front of the entire prom that she’s a 25-year-old undercover reporter. As mentioned, Mr. Coulson gets pissed and storms off. Josie’s brother is pissed because he now can’t play in the championship baseball game. Josie’s editor is pissed because there’s no story, and now they’re both getting fired. Josie solves everything by publishing a heartfelt apology in a rival paper, with a proposal: She will stand on the pitcher’s mound for five minutes before the big game and wait to see if Mr. Coulson shows up to forgive her. It’s not really clear why this fixes everything—there’s a vague idea that publicity is good for the school and the paper—but it does, and after the crowd cheers for five minutes straight (really!), Mr. Coulson finally shows up and forgives her.

The Verdict: Does not hold up!

Look, I don’t begrudge anyone who derives joy from Never Been Kissed. The jokes are great! Drew Barrymore’s dancing is classic! But I just hope that, now that we’re in the 21st Century, the Netflix rom-com resurgence will provide some slightly less problematic films to enjoy.

Stream Never Been Kissed on HBO