Like first sex, writer/director Maggie Carey's debut feature, The To Do List, is quick and messy, fitfully pleasurable, full of promise but not quite adept at getting everyone off. It's an impossibly huge deal yet also a modest achievement, something we have to go through but will no doubt be improved upon later. Here, at last, is the first raunchy mainstream comedy about a young woman's quest to unburden herself of her virginity — with the foxiest bro in Idaho, no less, a golden lug of shirtless flesh our heroine objectifies with all the male-gaze brio of Tex Avery's Big Bad Wolf pounding his noggin with a mallet at Red Riding Hood's nightclub act. Except the lust of valedictorian Brandy (played by and written for Aubrey Plaza) is deadpan, held inside, subject to the veto of her shame and intelligence. "You feel like Marky Mark looks," she marvels as she touches the abs of town hunk Rusty Waters (Scott Porter) at a graduation-night kegger, but when she kisses him, she's helpless, like she's trying to pick a lock with her tongue. That chance encounter crashes into drunken movie-comedy humiliation, but one thing does firm up nicely: her resolution to master sex — and Rusty Waters — before going off to college at summer's end.
That is both familiar and fresh. Unlike the hapless virgins in previous losin'-it comedies, Brandy knows she can get laid without resorting to trickery — she wants to learn to do it right, to master a skill she can't cram for. (The movie, to its credit, never pretends that Plaza doesn't turn boys' heads.) And unlike the female characters in previous sex comedies, sex for her is a straight-up choice, something she offers or refuses according to no agenda but her own. This is far from Revenge of the Nerds, where a costumed geek saves the day by sneak-fucking a clueless cheerleader, or from Young Frankenstein, where, with a song cue, Madeline Kahn's bride-to-be celebrates her own rape.
So the movie is something of a milestone. It's also funny enough, at times, to be recommendable on its merits alone, although there's something dispiriting about its junky look, indifferent pacing, and sketch-comedy characterization. Carey hails from the Upright Citizen's Brigade sketch and improv scene, and she knows how to craft a premise and build a joke. Her best idea: Overachieving Brandy plots out her sex life like a course syllabus, crafting a list of things to try before going all the way — hand job, blowjob, dry-humping. The film is set in pre-Google '93, so Brandy has to ask her friends (Alia Shawkat and Sarah Steele, given one good line apiece) what some of these even are — "pearl necklace," she presumes, is something a woman does to a man, something that "sounds elegant."
The comic high points, of course, are Brandy's efforts to engineer these sex acts, often with her lovesick ex-lab partner, Cameron (Johnny Simmons). They build to crowd-pleasing climaxes, laughter, and literal release. Since we're so many years past There's Something About Mary — and Bill Murray getting slimed in Ghostbusters — the eruption of semen is smartly played as a goofy triumph rather than an affront to good taste: Ejaculation is not the gross-out movies have so often made it; instead, it's more like an achievement you might unlock in a videogame.
Plaza is gutsy and often hilarious, both in small moments — nervously steeling herself for "finger-banging" — and when hand-jobbing away like she's trying to loose a bottle's last dab of ketchup. Between the sex scenes, though, The To Do List often flags, especially when Brandy is hanging around a local pool where — too conveniently — she, Rusty, and Cameron have all taken jobs. Carey resorts to puke, farts, and even some weirdly meta shit-eating. She also leans hard on '90s nostalgia, a much more meager vein than the boomer R&B mined in Animal House and The Blues Brothers. Here, the Spin Doctors are played as a joke, Big Head Todd is played in earnest, and 2 Live Crew's "Me So Horny" is an agenda-setting dare. Bill Hader occasionally stops the movie cold with impressions of Eddie Vedder and the neighbor on Home Improvement. He's supposed to be the shiftless manager of a Boise swimming pool, but when not assailing Brandy for the size of her breasts — a miserable recurring gag — he acts like a panelist on some God-awful VH1 show.
Brandy has lessons to learn about having sex with the right person, about communicating with a partner and not reducing life's richest pleasure to a checklist of acts. It's only midlist that it occurs to her that she should try masturbation — and discover how she likes to be touched. And it's only in the end, with a lover who isn't an experiment, that she discovers that her pleasure shouldn't be incidental.
Brandy's parents are wonderfully played by Connie Britton and Clark Gregg. Gregg, as a stern-ish judge, kicks back in bed with The Way Things Ought to Be, the '90s bestseller from slut-shaming man-turd Rush Limbaugh. That's a welcome reminder of this silly film's true seriousness. A lot of bastards out there will hate the idea of young women with a fuck-it list — or even enjoying sex at all. Fuck 'em, and not in the fun way.