requent “Student of the Month” Brandy Klark (Aubrey Plaza), in Boise, Idaho, is the anticipated valedictorian of Merriwether High School. In her graduating class of 1993, she holds the highest GPA – as well as the highest ever recorded in the history of the institution. Despite being smart, overachieving, laser-focused on future success, and downright gorgeous, she’s routinely mocked and incessantly bullied by her classmates, who heckle her speech until the principal removes her from the podium. “Get off the stage, virgin!”

Weirdly, she’s even belittled by her older sister, Amber (Rachel Bilson) – and this behavior isn’t stopped by their parents (Connie Britton and Clark Gregg). Brandy has an admirer, Cameron (Johnny Simmons), as well as best friends Fiona (Alia Shawkat) and Wendy (Sarah Steele), who are typical bad influences. Since Brandy has spent her best rebellious years following all the rules, remaining overly honest, maintaining perfect attendance, and observing proper grammar, it’s up to Fiona and Wendy to corrupt her – at least for a small period of time during the summer. And the most appropriate location for her righteousness makeover will be the local pool, where she’s going to be a new lifeguard – and where the boy she likes, hunky college guy Rusty Waters (Scott Porter), happens to work. “You blew a major opportunity.”

After a “Napoleon Dynamite” type of visually creative opening title sequence, the film makes use of its hard-R rating, with plenty of sexually explicit conversations as Brandy, disappointed in her lack of experiences with the opposite sex, forms a list of adventurous activities (many of which, she has not the slightest clue as to their meanings) to engage in before she accomplishes her ultimate goal: intercourse with Rusty. “Teabagging. Must be British.”

Although the film is filled with recognizable faces – including Bill Hader, Christopher Mintz-Plasse, Donald Glover, Andy Samberg, and more – the many roles don’t add much. It all boils down to nerdy Brandy’s misplaced interests and her eventual recognition of what’s important. In the meantime, countless sequences delve into the uncommon theatrical topics of masturbation, orgasms, circumcision, semen, breast size, promiscuous sex acts, drugs, and foul language – all involving teens (carrying on from where pictures like “Superbad” set a bar). Irresponsibility, friendships in crisis, emotional distances, and genuine romantic feelings do crop up, but they never feel sincere.

The main problem with “The To Do List” is that it’s only intermittently funny. A few scenes are amusing, but for the most part, the film substitutes genuine hilarity with overwrought raunchiness; it aims to be edgy rather than humorous (it touches upon the ideas of the “American Pie” series, but in reverse, from the woman’s viewpoint, and without the benefit of being one of the first of the genre). Mild comic mishaps and pranks (primarily involving carnal escapades gone awry) pose light chuckles, but laugh-out-loud moments are practically nonexistent. At least the finale presents a sex-positive perspective, though it’s thoroughly questionable when Brandy’s mother offers lube as a priority over prophylactics after a birds-and-the-bees talk.

– Mike Massie