Three years after entering prison for robbery as a 19-year-old heroin addict, Sherry Swanson (Maggie Gyllenhaal) begins her first day of freedom, clean and sober. A model prisoner who has undergone personal transformation, she immediately sets out to regain custody of her young daughter Alexis (Ryan Simpkins), who has been cared for in her absence by her brother Bobby (Brad Henke) and his wife Lynn (Bridget Barkan).
Unprepared for the demands of the world she’s stepped back into, Sherry’s hopes of staying clean, getting a job, and becoming a responsible mother are challenged by the realities of unemployment, halfway houses, and parole restrictions. Bobby and Lynn’s concerns about Sherry’s ability to care for Alexis, and her inability to prove them wrong, threaten to destroy the already delicate relationship she has with her daughter, as well as her newfound sobriety.
Disillusioned and haunted by wounds from her childhood, Sherry is eventually confronted with life-altering questions about her own survival and what it means to be a good mother. Ultimately she learns that as the harsh realities of life often get in the way of her best intentions, sometimes it’s best to take life one small step at a time.
Trejo (pronounced Treh-ho), a Mexican American, was born Dan Trejo, Jr. in Los Angeles, the son of Alice Rivera and Dan Trejo, a construction worker. He is a cousin of filmmaker Robert Rodriguez and a native of the Echo Park neighborhood of Los Angeles. As a youth, he roamed the streets around his home area, committing various crimes and became addicted to drugs. He was in and out of jail many times as a teenager.
While on the streets, Trejo developed talent as a boxer and considered taking up boxing as a profession. That ambition was dashed by a lengthy prison sentence. While serving time in San Quentin State Prison, he became the California state prison champion in both the lightweight and welterweight divisions. During this time, Trejo became a member of a twelve-step program, which he credits with his success in overcoming drug addiction.
When we first see Dean, he doesn't seem impressive. Besides being an addict, he's eager to sleep with Sherry while he has another woman on the side. But soon he seems to be reasonably committed to Sherry. He says he'll be her friend as well as her lover. He takes her home after she gets high, and drives her to her daughter's birthday party. It appears he'll be a stabilizing and possibly long-term presence in her life.
Sherrybaby isn't deep but it's well done. This review from IMDB.com kind of captures how I feel about it:
Certainly all performances in the film hold up pretty well. It is especially interesting to see Danny Trejo in a role in which he is actually nice for a change--a bit of a sleaze, true--but still on the side of good (as opposed to rentable bad-guy/thug). All the interactions between the characters follow the theme of the film; it is realistic. But 'Sherrybaby' is not devoid of faults. At all. One of its key shortcomings is its lack of any clear point. You get the feeling most scenes do not serve any purpose other than to give us a feel for the way things are run (wow, I feel like I'm writing about Scorsese) in the white trash culture.