Maggie Gyllenhaal as Sherry Swanson
Brad William Henke as Bobby Swanson
Sam Bottoms as Bob Swanson, Sr.
Kate Burton as Marcia
Ryan Simpkins as Alexis Swanson
Giancarlo Esposito as Officer Hernandez
Danny Trejo as Dean
Rio Hackford as Andy Kelly
Bridget Barkan as Lynette Swanson

Directed by Laurie Collyer

Laurie Collyer’s heartbreaking indie drama is mostly noteworthy for Maggie Gyllenhaal’s realistic portrayal of a troubled woman trying to get back her daughter after getting out of jail.

Sherry Swanson (Maggie Gyllenhaal) has just been released from prison after three years. She’s trying to get back on the right path and reconnect with her young daughter Alexis (Ryan Simpkins), who has been raised by Sherry’s brother and his wife. They’ve grown attached to the girl and don’t believe that Sherry has cleaned up and is responsible enough to care for her, creating more problems for Sherry on her attempts to find a new life.

Another great indie find from this year’s Sundance Film Festival, “Sherrybaby” is neither instantly loveable like “Little Miss Sunshine” nor magical like “The Illusionist,” instead being a gritty real-life story of a woman whose story could reflect any one of thousands of women released from jail every year, trying to start their lives anew. Some succeed, many fail, and “Sherrybaby” is based on the story of a woman who ends up somewhere in between.

The big difference between Sherry Swanson and the usual women who end up in jail is that she’s young, pretty with blonde hair and the looks of a model, but she also comes from a well-to-do middle class family. Something happened that led down a path of drugs and stripping jobs before being jailed for three years, presumably on drug charges. Jail has toughened her up, making her more stubborn and headstrong, and at the halfway house that’s her new home, she immediately gets into fights with the older women, because they don’t like her good looks and condescending attitude towards them. You can tell that Sherry is used to coasting through life on her looks and using her sexuality to get what she wants from the men she meets; she even performs a sexual favor to get a job she wants working with kids. Her no bullsh*t parole officer, played by Giancarlo Esposito, is not so easy, knowing that he has to be tough with her to get through and making it clear that he won’t hesitate to throw her back in jail if she starts doing drugs again.

All this stuff doesn’t bother Sherry, because she’s more concerned about being with her daughter Alexis who has been cared for by Sherry’s brother and his wife. They’ve both grown attached to Alexis and they don’t think Sherry is able to care for her. Sherry’s childlike nature allows her to get along great with kids, but her lack of good judgment makes it hard for people to trust her. On top of everything, her brother’s daughter has trained Alexis to call her “Sherry,” igniting Sherry’s greatest fear, that she’s lost her daughter and her motivation to clean up her act. It’s surprising that Sherry doesn’t have the support of her family when she gets out, but as we learn, her family issues may have contributed to her drug use in the first place. We can only imagine what Sherry must have done before going to jail to earn such distrust from her family, and it makes the story more intriguing because we’re only given a few clues to what happened. Wisely, the movie never uses flashbacks and Sherry rarely talks with anyone about what happened before she went to prison.

The movie is fairly harsh and to the point, rarely sugarcoating what it’s like to be on parole after going through the penal system, and it doesn’t skimp on the details in trying to show this experience. The realism of the dialogue and the situations makes it a jarring experience, a lot of that coming from director Laurie Collyer and cinematographer Russell Fine’s “fly on the wall” technique, which one presumes is born from their experience making documentaries. Despite the movie’s low budget, it really does look great.

Though Collyer spent years researching the movie and reworking the script, it really is Maggie Gyllenhaal’s movie, since few other actresses her age could have pulled off such a tough role, acting the way she does but still creating a sympathetic character. This amazing performance makes Sherry’s plight is even more heartbreaking, but Gyllenhaal brings just enough of the childish wonder to the role to make you care about her and forgive her when she flips out or falls off the wagon.

Gyllenhaal spends a lot of the movie in clinging and revealing clothing, or no clothes at all, but Collyer makes sure that it’s more to enhance the realism rather than using the nudity and sex in an exploitative way. It really is almost the exact opposite to Roger Corman’s ’70s women’s prison movies, while also being less outlandish than Park Chan-wook’s recent “Lady Vengeance.”

The entire cast is great–it’s always great seeing Brad William Henke–but there’s a particularly strong supporting performance from Danny Trejo, the tough Mexican from Robert Rodriguez’s films, as a sympathetic AA sponsor who means well, but who also ends up taking advantage of Sherry’s vulnerable state.

More important than anything else, “Sherrybaby” never tells you what to think about its main character or the people around her. It never makes judgments, allowing the viewer to decide whether Sherry deserves what happens to her, and which influences in her life are the bad ones. A lot of it can be depressing, but where Sherry ends up seems to be in a better place, at least in terms of her mental well-being, than where she is at the beginning of the movie.

The Bottom Line:
Sure, many people might find this movie to be a bit of a downer, because nothing seems to go right for its main character. Some might feel that Sherry deserves what happens to her because of her attitude and drug use, but others, particularly women, may understand why she feels pressured to do some of the things she does. Either way, fans of independent filmmaking who know what great writing and performances can come out of such labors of love, should be able to appreciate the way that Collyer and Gyllenhaal create a very real portrayal of this troubled woman and offer a muted rainbow at the end of the storm.

Sherrybaby opens in New York and L.A. on Friday, September 8.

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Weekend: Nov. 22, 2018, Nov. 25, 2018

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