Never Been Kissed (1999)

Don't worry baby, Everything will turn out alright
Never Been Kissed sees Drew Barrymore's copy editor, Josie Geller, yearn to be a reporter. Something that comes her way when by way of a fluke, she's selected for an undercover mission at High School. Trouble is, is that she's got to be 17 again, and that's something that brings back all of those horrible moments from her high school days. The time of having no friends, the butt of the jokes and ignored by the boys (all told in cringe inducing flashbacks).
Cue much fun as the 25 year old Josie not only tries to bluff everyone that she's 17, but tries to fit in with the youth who have considerably changed from back in her days. Enter cool as ice brother Rob (David Arquette) who decides to lend a helping hand, with some funny and excellently scripted results. Not only this but we of course have the obligatory love interest, only this is a kicker as it concerns Josie's teacher Sam (a sickeningly handsome Michael Vartan). Cue Sam on mind overload as his feelings lead him onto what he thinks is morally dubious ground...
It's as frothy as can be is this one, perhaps in the running for the 90s most chickiest ckick flick? But, and I say this as a middle aged guy, the jokes are spot on, it's endearing as heck and it boasts a quite marvellous turn from Barrymore. It's the sort of performance that could light up the most turgid of comedy movies. It's a threefold character portrayal of some depth and no little charm. She's well supported by the always likable Arquette, while notable turns also come from John C Reilly, the ever reliable Molly Shannon and Leelee Sobieski. While the sharp eyed will spot future Green Goblin James Franco and Susan Storm herself, Jessica Alba, nestling in amongst the teen performers.
Nothing remotely new here, but for some genuine laugh out loud comedy moments, a feel good factor soaring through the roof, a kick-ass soundtrack and Barrymore herself, this is more than recommended as a pick me up movie. 7.5/10

Good watch, could watch again, and can recommend.
Look, I have some fairly negative memories of this movie over the years, and I'm not saying it is the best, but for all its flaws, it holds up surprisingly well.
The idea of Drew Barrymore (even in 1999) being able to pass for a high school student is nonsense. I'm not that big a fan of hers, but she nails this role even if she's clearly an adult at high school, but what the movie is about, and what she expresses wonderfully is the emotion of being in the traumatic experience of high school when you're not part of the ruling class.
I feel like they casted well enough: David Arquette, Molly Shannon, J.C. Reilly, Leelee Sobieski, and Cress Williams (Black Lightning) all do great support roles, and Jessica Alba, Mary Shelton, Jordan Ladd, and all do great antagonist roles.
The writing of writing about a story, in a story of one character hiding herself in another story is oddly meta on a few levels, but it remains complex without being overly complicated, is still funny, and has plenty of substance.
While I don't imagine I'm going to watch this very often, I'll have to credit my mother: this is worth the watch, even after 20 years.