Like the recent Half Nelson, the main attraction (for both the audience and the star) of Sherrybaby is the strong lead performance from Maggie Gyllenhaal (Trust the Man, World Trade Center).   Aside from a spectacular performance in Secretary, Gyllenhaal has typically lurked in smaller, less flashy roles.  Here, as Sherry Swanson, she proves that she has what it takes to make it in the big leagues. Swanson is fresh out of jail and a recovering addict.   She wants to start her life again, but is having an extremely difficult time doing so.

Sherry's primary concern is regaining custody of her daughter Alexis (Ryan Simpkins).  Sherry's brother Bobby (Brad William Henke, World Trade Center, North Country) and his wife Lynette (Bridget Barkan, Stateside, Everyday People) have been caring for her while Sherry was in jail.  And while Sherry wants to be a good person and a good mother, she simply does not know how to do so.   She is unwilling to work hard to get what she wants, always preferring to take the easy route.  She lashes out at any potential setback, and comes dangerously close many times to relapsing in the face of adversity.

The deck stacks against her quickly.  She moves into a halfway house but has serious problems getting along with the other women.   Sherry wants a good job, but when she doesn't get it, she trades sexual favors for it.  She refuses to follow simple rules around her probation.   Her life is a train wreck waiting to happen, and it's hard watching Gyllenhaal go through the steps.  Writer/director Laurie Collyer has Sherry make all the wrong choices, and it just causes her to spiral further out of control.   Collyer does a few things that don't really make much sense, but do help contribute to Gyllenhaal's feeling of helplessness.  Bobby and Lynette seem to be trying to take Alexis away from Sherry.   They tell her to call Sherry by her name instead of "mommy."  It is the worst feeling of betrayal for Sherry, who is frustrated that she cannot do anything about it.   Because Collyer tells Sherrybaby from Sherry's point of view, she never explains why they feel this way.  Worse, she throws in a scene with Sherry's father that feels highly contrived.

But even with some of the plot issues, Gyllenhaal is still mesmerizing to watch on screen.  Her performance consists of wildly fluctuating emotions – fear, anger, desperation, frustration, and fatalism, all at the same time.   As she gets worse, Sherry lashes out at everybody around her, until she finally gives up, and stares out into space with hollow, soulful eyes.  It's an extremely strong performance, and heartbreaking to watch her slowly fall apart