Gyllenhaal is riveting, but Sherry is a hard woman to like -- selfish, immature, willing to sleep with pretty much any man she comes across if she thinks it will get her something she wants. Director/screenwriter Laurie Collyer has focused her film primarily on the relationship between Sherry and her daughter's surrogate family: Sherry's brother Bobby (Brad Henke) and his wife Lynette (Bridget Barkan), who are wary and protective about the child they've come to view as their own. There's something oddly schematic about this pivotal conflict -- Barkan in particular lingers in the mind as a kind of endless montage of rolling eyes, hostile glances, and hands that reach out to take Sherry's daughter Alexis out of the room whenever Sherry is trying to get close to her. But the compassion of Collyer's attitude toward her wayward and ultimately victimized protagonist slowly builds into a powerful statement on the possibilities of redemption for even the most lost, and "Sherrybaby" manages some lovely emotional moments in the end.
In a solid supporting cast, veterans Giancarlo Esposito and Danny Trejo stand out for bringing layers of complexity to roles that were probably more sketched than drawn on the page. Esposito's non-nonsense parole officer is so carefully modulated that when the slightest suggestion of compassion toward Sherry flickers across his face, it's more moving than a far more demonstrative display could ever be. Trejo believably moves from unlikely lover to surrogate dad with straightforward grace. Visually, this may be a more workmanlike film than it had to be -- some mostly improvised scenes between a radiant Gyllenhaal and some inner-city daycare kids suggest that a looser approach to the material might have yielded unexpected dividends. As Sherry's daughter Alexis, child actress Ryan Simpkins is an utter delight. Starring Maggie Gyllenhaal, Brad Henke and Bridget Barkan. Directed and written by Laurie Collyer. Produced by Lemore Syvan and Marc Turtletaub. No distributor set. Drama. Not yet rated. Running time: 96 min.