Avoiding cliches, Sherrybaby tells the story of a drug user and ex-con trying to reconnect with the daughter she barely knows. Maggie Gyllenhaal plays the part with raw conviction and she is ably supported by a well-chosen cast.
At the start of the film, Sherry (Gyllenhaal) has just been released from prison and must report to a parole officer, Hernandez (Giancarlo Esposito), in order to arrange housing and employment. Right away, Sherry defies her legal guardian by requesting to meet with her young daughter (Ryan Simpkins), who is being cared for by her passive brother (Brad William Henke) and bitter sister-in-law (Bridget Barkan). Later, Sherry further tests her parole status by leaving the halfway house where she is assigned and moving into her brother's house.
The awkward reunion with her daughter, tensions with her other family members, and difficulty getting a job lead Sherry to return to her old, bad ways, including drinking and having unprotected sex. After realizing that early childhood sexual abuse was at the root of many of her problems, Sherry also starts taking drugs again.
Because of her transgressions, Sherry nearly lands back in jail, but she is shown mercy by Hernandez. In the end, she makes the painful decision to get in-patient treatment for her debilitating addictions, even though it will keep her apart from her daughter.
While little about the narrative is surprising or revealing (even the incest theme), the personal and honest way Collyer tells Sherry's story makes it riveting. There are a few minor lapses, such as when Sherry's resentful sister-in-law (wonderfully played by Barkan) doesn't register any objections to Sherry's moving in, but, for the most part, the narrative seems true-to-life and uncompromising. Collyer's focus and approach is reminiscent of the work of Alison Anders (Gas Food Lodging, Mi Vida Loca) and the lack of flourish is appropriate. (This is no Requiem for a Dream.) On the other hand, the few moments of "style" stand out strongly, such as the turning point where Sherry resumes her drug use (a montage beautifully scored by Jack Livesy).
Best of all, there are no false notes in the performances. Everyone is believable and "real," from Gyllenhaal (brave in a demanding role) to Barkan, Henke, Esposito, Sam Bottoms (as Sherry's father), Danny Trejo (as Sherry's most caring lover), and Ryan Simpkins (a standout as Sherry's troubled daughter). Only Kate Burton is wasted in a bit part playing Sherry's mother-in-law.
Though downbeat in subject and not always easy to watch, Sherrybaby is a harrowing journey well worth taking.