Starting all over is a huge challenge to those paroled from prison. The deck seems to be stacked against them. Their movements are closely monitored by a parole officer; they must find work and a place to stay as soon as possible. Oftentimes old friends are out of the question since they may have contributed to the criminal behavior that got them in prison. Family members may have mixed feelings about welcoming an ex-con back in their lives. Worst of all, are employers and other so-called normal members of society may see them as nothing but damaged goods. It is a hard and lonely road to a new life after doing time.
Sherry Swanson (Maggie Gyllenhaal) has just been paroled after serving three years in prison for robbery. She is a recovering heroin addict and must immediately check into a halfway house. An angry woman there immediately dislikes her, assuming Sherry thinks she's better than everyone else. Parole Officer Hernandez (Giancarlo Esposito) is a no-nonsense man who makes it clear to Sherry that she must follow the rules and stay on the straight and narrow path of rehabilitation. He gives her permission to see her brother Bobby (Brad William Henke) who with his wife Lynnette (Bridget Barkan) has been looking after Alexis (Ryan Simpkins), Sherry's young daughter. They have bonded with the little girl and are uneasy about her mother's visit.
In an interview, writer and director Laurie Collyer has stated: "Sherrybaby is a film about hope — the hope of a young woman trying to reconnect with her child after a long hard road of drug addiction and prison time. It is a desperate, almost primal hope which exists beyond reason. But this is truly what hope is — an indomitable spirit that keeps us believing that life can be what we imagine. As a character, Sherry Swanson is the embodiment of hope because she has nothing left to believe in, and yet she still believes." Collyer teases a top-drawer performance out of Maggie Gyllenhaal who demonstrated her great talent in Secretary.
It is easy to cheer for Sherry as she struggles to fulfill her high hopes as a loving mother. But she tries too hard and comes off as a smothering parent whose neediness gets in the way of what she wants. She uses her sexual allure on an employment agent who then gives her a job working with children. Sherry claims to rely more on the Bible than the 12-step program but she does find a friend in Dean Walker (Danny Trejo) who has seen and done it all. He nurtures her when she needs it most. Sherrybaby is an engaging film that vividly conveys one ex-con's struggle to turn her life around.
