It's pretty likely that The To Do List will hold a place in cult comedy round-ups for years to come, and that as many people will love it as loathe it. It's one of those just barely over-the-top summer ensemble pieces near custom built for derision, a sort of Wet Hot American Summer-type affair with a cast pulled from every TV show on a comedy geek's short list of favorites. Nearly everything about it sounds awesome: Aubrey Plaza unlocks the lead actress achievement, it's a lady-centric sex comedy about a smart girl taking control of her own shit, and, again, the cast boasts a solid line-up of characters. It sounded like a near sure thing. Plaza's character Brandy Klark is the tightly-wound 1993 high school valedictorian. After being taunted for her virgin status during graduation, Brandy rips her old list of goals from her tropical trapper keeper and, aided by her trampy older sister (Rachel Bilson), maps out a new summer plan of sexual exploration. Before going to college, Brandy hopes to have tried her hand at everything from hand jobs to dry humping to full on intercourse (with the town stud, of course). Like the nature of her to-do list itself, though, Brandy's story is somehow better on paper than it is in practice.
The To Do List kicks things off with a tremendous amount of promise. One of its great strengths is its attentiveness to evoking a near constant 90s nostalgia via its mise en scene. The tour of Brandy's 1993 bedroom in the opening credits (set to "Me So Horny") is fabulously out of date, and the genuine disinterest in taking on the story post-internet works heartily to the story's advantage. This is a time of scrunchies, crop tops, and Jason Priestley posters - not of Snapchat, Tumblr, or any degree of sexting. Everything has to be done the "old fashioned" way, and in scrawling out a hand written list of foreign sounding challenges ("Teabagging. Must be British?") without access to the wide, frightening world of internet porn, Brandy has her work beyond cut out for her. This is the concept that makes the movie funny at its best moments, but also part of its downfall. The To Do List is repetitive and relies too heavily on a concept instead of actually writing enough jokes for its run-time. The way it pans out is basically like so: Brandy writes the list, Brandy works on executing the list, we watch Brandy stumble through it. If you start to imagine how awkward one sexual act is in your average teen comedy, think about how old it could get watching a film where the premise is an unending series of that same fumbling.
To an extent: it is funny. More often than not, there's something quaint and charming about The To Do List. Amid all the graphic conversation, off-color sex jokes, and bodily functions, the movie manages to fall on the side of too cute in ways that can't be explained. All well and fine, but the cuteness clashes with some immediacy against the movie's desperate need to push its gross-out, bodily humor to a place where it's more shocking or repulsive than funny. There's some nasty ass business in this sex comedy. Like, a pool scene that steps into Pink Flamingos/Divine territory with zeal. The moods are so extreme that the jokes and story just can't keep up, and the whole thing seems trapped in this place where it's trying to prove something it shouldn't have to. Frankly, it'd be a better, smarter movie if it played out with a character more like the live-action Daria Plaza played so effectively in the short for College Humor.
Which brings us to a sad truth: Plaza isn't that great as Brandy. While she steps away from the deadpan box of Parks and Recreation and wears the gawky teen guise well, she's a bit rigid and there's something in her eyes that belies crucial aspects of her character. When she needs to look more naive, when we need to feel some sort of empathy for her, we can't. The reason why she works so well playing April on TV is exactly why she doesn't quite hit the mark with Brandy: she looks like she's in control when she shouldn't, like she's smirking when she's meant to be embarrassed. A secondary problem is, of course, that the writing doesn't really allow Brandy to have as much dimension as she should. The awkward, proud nerd we meet early in the film doesn't come across as the risk taker Brandy is quickly established as being, and the further she gets into her list, the more unbelievably stupid her behavior becomes. She's an uneven character in an uneven film, and though there's much that's entertaining throughout, The To Do List just doesn't meet its goals.