But while The To Do List has its share of Wedding Singer-ish gags (centering around the somewhat more specific 1993 rather than Singer's mid-decade catch-all 1985), its timeline has uses beyond nostalgia on the part of its prospective audience or its writer-director Maggie Carey: it creates a plausible environment of simultaneous sexual openness and cluelessness, keeping graduating high school senior and valedictorian Brandy Klark (Aubrey Plaza) from researching her newfound sexual curiosity on the Internet (although, let's be real: wouldn't a real-life Brandy Klark maybe dial up to a BBS or two in 1993?). Plaza, as a comedian, is known for deadpan surliness, and even though Brandy's uptightness earnestness precludes her usual sarcasm, Plaza's pitiless eyes and monotone are still put to good use. As it turns out, her disaffected hipster persona is not so far off from an irritable nerd.
Brandy's best friends Fiona (Alia Shawkat) and Wendy (Sarah Steele) have wilder streaks, and when they drag her from her college to-do list long enough for a drunken party, Brandy lays eyes on a hot boy, embarrasses herself with her lack of experience, and decides to create a new list: sex stuff to try before she goes off to college. She also gets a job lifeguarding at the local pool run by Willy (Bill Hader, Carey's real-life wife); spars with her older sister Amber (Rachel Bilson, surprisingly well-cast) and, yes, if we must, contends with the affections of a guy she sees only as a friend (Johnny Simmons). After the movie sets up Brandy's list, it's basically a series of sketches allowing Plaza to take the lead in enacting dirty jokes with even more comic guest stars: Andy Samberg (very funny), Donald Glover (sadly underused), Christopher Mintz-Plasse (didn't he graduate in 2007?), and so on. The construction is choppy and the filmmaking not always graceful, but The To Do List is very funny—and to its credit, keeps the rom-com BS to a minimum; Brandy gets to draw some conclusions in re: the big deal about sex that are so worthwhile (and relatively sex-positive and laid back) that it's almost better that they're hit square on the nose. Moreover, the cast is so varied and talented that watching the endless combinations and recombinations of actors becomes sort of like watching a good version of an endlessly 'shipped and re-shipped 90s TV cast. The Way Way Back is this summer's more heartfelt ensemble coming-of-age comedy involving pool maintenance. But The To Do List is a funnier, wilder, and, in its sloppy way, better alternative.