Sherry Swanson is a junkie ex-con struggling to stay sober, develop a relationship with her young daughter and find some meaning in her existence. She doesn't have the skills to do any of those things well, however, which leads to increased frustration and continued poor choices. Sherry's damaged, but she won't face the realities of her challenges. Something happened to her during childhood that warped her sense of self; she needs something or someone to make her feel good about herself, because she can't get to that place alone.
Most times that something is heroin. Other times it's found in how she manipulates men.
Maggie Gyllenhaall is remarkable as the lead in Sherrybaby. In perhaps her most substantial role since Secretary, Gyllenhaal displays incredible range: she is at different times desperate, independent, insecure, tough and even sexy.
Gyllenhaal morphs Sherry through these emotions and traits in very subtle ways, and always in convincing fashion.
As good a Gyllenhaal's acting is in this movie, Sherrybaby is difficult to watch. The character's main goal is to regain custody of her young daughter, all the while unaware--as the audience clearly is very much aware--that she does not have the skills to be a good mother. As she gets closer to that goal, it's difficult to remain sympathetic to the character.
We simply don't want her to have her daughter, because we know the harm it would cause the child.
Sherrybaby is an honest, in-depth look inside the life of a young woman who never had much of a chance to succeed. As tough as the film is to watch, it's honest. And that makes it worth the viewing.