Former American President Calvin Coolidge once postulated that his country's most common commodity is unrealized potential. Few of us can claim not to possess it, but it takes a special sort of underachiever to match the feats of Imogene (Kristen Wiig), a playwright once thought to be destined for greatness, but who has spent most of her twenties and thirties frittering away her talent and opportunities. As Imogene begins, she's just about hit bottom, having staged a suicide attempt in a desperate bid to hold on to her philandering boyfriend - it's about the only thing she's staged in a very long time. And it's not a hit.
Things can only go up from here, and they do in this wildly quirky and weirdly optimistic comic character study. After her fake suicide attempt, Imogene is remanded to the custody of her mother (Annette Bening), a blowsy, overbearing gambling addict with a friendly but somewhat seedy goof of a boyfriend (Matt Dillon) who claims to be working for the CIA. This unexpected homecoming forces Imogene to confront her lingering feelings about her long-dead father, but it also finds her developing a surprising intimacy with her mother's lodger, the much-younger Lee (Darren Criss), a singer currently exhibiting his talents in a Backstreet Boys cover band. Lee would seem anything but substantial on the surface, yet his sincerity and intelligence is arresting, and he may be just what the doctor ordered for our recovering heroine.