Film
Never Been Kissed
A newspaper copywriter goes undercover as a high schooler to get the teen-culture scoop she can't write from adult experience, and promptly relives every humiliation she thought she'd escaped. It's frothy, earnest, and openly nostalgic for the John Hughes era it's imitating. Watch it for Drew Barrymore's genuinely disarming lead performance, not for narrative rigor.
If you liked this
10 Things I Hate About You1999
Same year, same teen-movie renaissance, but sharper and funnier, with a Shakespeare backbone holding the romance together. Heath Ledger is impossibly charming and the banter still holds up.
But If you want Josie's sweetness rather than Kat's spikiness, this one runs colder and more sarcastic.

Easy A2010
Emma Stone's breakout, and a smarter update of the high-school-reputation plot — funnier, more self-aware, and honest about how fast rumors calcify into identity.
But It's talkier and more ironic than Never Been Kissed's earnest romanticism; less swoon, more satire.

13 Going on 302004
Flip the premise — an adult trapped inside her teenage fantasies instead of the reverse — and you get the same wistful ache about who you were versus who you became.
But Leans harder into magic-realism whimsy; if you wanted grounded awkwardness, this is broader and glossier.

The wildcard
Something you would not have found on your own.
Peggy Sue Got Married1986no page yet
Same engine — an adult forced back into adolescence to reckon with a self she'd outgrown — but played as wistful drama instead of comic fantasy, thirteen years before Josie tried it for laughs.
Kathleen Turner, playing a disillusioned adult who wakes up back at her own high school reunion and then, impossibly, back in her teenage body, wrestling with who she used to be.
But Slower, more melancholic, and genuinely interested in regret rather than romance-as-redemption.
More like this (8)
Mean Girls2004
The definitive map of high-school social terrain that Josie is trying to infiltrate — quotable, vicious, and precise about clique anthropology.
But Meaner and more cynical throughout; the romance is a footnote, not the engine.

The Wedding Singer1998no page yet
Barrymore again, a year earlier, radiating the same wounded optimism, this time opposite Adam Sandler in one of the most purely likable rom-coms of the decade.
But No high school at all — different setting, different decade nostalgia (80s wedding culture instead of 90s teens).
She's All That1999
The mirror-image makeover plot, same release year, same prom-centric climax — a nice double feature if you want to marinate in exactly this moment in teen-movie history.
But Thinner characters, more overtly a bet-driven gimmick than an emotional journey.

Clueless1995
The gold standard this whole genre is quietly indebted to — witty, stylish, and warmer to its heroine than most teen comedies bother to be.
But No adult-undercover twist; if that's the specific hook you wanted, this plays it straight.

Music and Lyrics2007no page yet
Barrymore a decade on, still doing endearing-klutz-finds-love, this time against Hugh Grant's washed-up pop star. Comfortable, low-stakes, reliably charming.
But No high school setting or coming-of-age angle; it's a straightforward adult rom-com.
EverAfter1998
Barrymore's Cinderella riff, made the year before this one — proof she could carry a period romance as easily as a teen comedy.
But Completely different register: fairy-tale drama, not comedy, and set centuries earlier.

Welcome to the Dollhouse1996
It's the same high-school caste system Josie infiltrates, minus the fantasy that popularity or love fixes anything — the corrective register to Never Been Kissed's sweetness.
The unglamorous, unglossed version of the same social battlefield — a genuinely uncomfortable, blackly funny portrait of middle-school cruelty with no makeover arc waiting at the end.
But There's no romantic rescue, no happy prom; it sits in the misery rather than resolving it.

Freaks and Geeks1999
Released the same year, obsessed with the same outsider-trying-to-belong dynamic, but stretched into episodic form so the awkwardness gets room to actually breathe instead of resolving by the credits.
An 18-episode time capsule of the exact same high-school landscape, told with more patience and specificity than any single film could manage, and stuffed with future stars.
But It's a serialized commitment, not a two-hour hit, and its comedy is quieter, sadder, less tidy.

People
Cast
Drew BarrymoreJosie Geller
David ArquetteRob Geller
Molly ShannonAnita
Michael VartanSam Coulson
Jessica AlbaKirsten
John C. ReillyGus Strauss
James FrancoJason
Octavia SpencerCynthia- Jenny BicksMiss Haskell
Garry MarshallRigfort
Sean WhalenMerkin
Cress WilliamsGeorge
Directing
- Raja GosnellDirector
- Richard GravesFirst Assistant Director
- Benita BrazierScript Supervisor
- Susan J. HellmannSecond Assistant Director
Writing
- Abby KohnScreenplay
- Marc SilversteinScreenplay
- Jenny BicksWriter
Production
- Justine ArtetaCasting
- Kim Davis-WagnerCasting
- Jeffrey DownerCo-Producer
- Drew BarrymoreExecutive Producer
- Nancy JuvonenProducer
- Sandy IsaacProducer
- Steven J. JordanProduction Designer
- Jack L. MurrayProduction Supervisor
- Jeffrey DownerUnit Production Manager
Recommended by
10 Things I Hate About You, Easy A, She's All That, 21 Jump Street, The Truth About Cats & Dogs, 13 Going on 30, Sierra Burgess Is a Loser