I’m liking Maggie Gyllenhaal the more I see of her (having now seen a whopping two movies of hers). I don’t mean just that she’s hot. She is, but purely on looks, she isn’t quite at the superstar level of hot.

I think it’s that she has more of an intriguing sexuality to her because her characters have complexity or brains or a little something on the ball. Plus her looks are a little different from the typical hot woman that everyone goes nuts over, and a lot of times—including with her—that kind of offbeat look grows on me and I find such women especially interesting to look at.

Both here and in the other movie I’ve seen with her in the lead (Secretary), she does quite well in what I would have to think are difficult roles. In Secretary she plays scenes where she has to be sexy, but with enough of an offbeat fetishistic oddity to get laughs, without thereby undercutting the sexiness.

And she pulls it off. She’s very erotic in that movie, yet at the same time you’re aware there’s an undercurrent of playing the unconventional sex at least a little bit for laughs.

In Sherrybaby she plays another highly sexualized role, another troubled character with a lot going on inside her. Again she succeeds in manifesting a certain raw sexuality, yet having a lot more complexity and nuance to her than just that.

Gyllenhaal plays a junkie trying to get clean. She’s just been released from prison. She moves into some kind of group home or halfway house, though she also stays part time with her brother and sister-in-law, and later with an Indian guy she’s seeing. She has a tough guy parole officer to report to. She needs to work, attend AA type meetings, and stay clean to stay out of prison, and to reclaim her young daughter, whom her brother and his wife have been taking care of in her absence.

So in that last respect it’s the same as Clean—a junkie whose motive to get off drugs is to regain custody of her daughter. I preferred this movie’s handling of the theme better, perhaps because I find Gyllenhaal more intriguing to watch as noted above.

I kind of went back and forth on how realistic her portrayal is, but ultimately decided it is mostly convincing.

At times I wanted to say that even though she has some issues, she’s maybe just a little too sharp, a little too strong, a little too functional for someone who has messed up her life with drugs and is just getting out of prison. But I suppose there are all levels of competence amongst people who operate on the seamy side of life—the junkies, the sex workers. (She’s been a stripper—underage for a time—done at least some hooking, etc.) I’ve known a few women—not all that many and most of them not all that well—who had something like that kind of life, and it’s not like they were all fucked up to the same degree. Some were at least somewhat competent.

And that’s really all she is. Somewhat competent. Not a pure victim. Not a hopeless case. More dynamic and self-directed than the stereotypical junkie you’d see in a movie, and probably more dynamic and self-directed than the average junkie in real life. But limited enough, and prone to fuck ups enough, to still be within what I would think is a realistic range.

As I mentioned, she’s a very sexual character, and that’s part of what makes her interesting. She instinctively bargains with sex to get what she wants. She needs a favor, she needs somebody to bend a rule, she needs a loan, she needs someone to take her side in a dispute—whatever—if it’s a guy, she plays the sex card. Whatever will be enough to cause them to want to repay her, whether it be flashing her tits, going down on them, or spreading her legs.

Sometimes it works in getting her what she wants, sometimes it doesn’t. But it certainly works often enough for her to continue trying it regularly.

Her attitude toward it fascinated me. She comes across as very neutral and businesslike about it. It’s just a transaction, or attempted transaction. She gives no indication that she has contempt for men because she can manipulate them, nor that she feels angry or victimized because they put her in semi-coercive positions where she has to let them take what they want from her sexually. She doesn’t seem to think less of herself because of it, nor does she come across as arrogant about it, like she’s proud of how successfully she does what she does. She isn’t bemused by the men. She doesn’t seem to have a special respect for those who don’t succumb to her charms.

No, it’s all a lot more neutral and unemotional than that. She doesn’t seem to have any more of that stuff going on inside her about sex than about any other transaction, any other way of influencing people to help you in some way.

Maybe you get a loaf of bread by handing over cash for it, you get somebody to let you change lanes by flashing a smile and gesturing, you get a child to stop annoying you by using a certain tone of voice when addressing him or her, you get someone to buy your car by speaking rapidly, confidently, and knowledgeably, and so on. Rarely do you stop and analyze any of it. Rarely do you feel much about it. Guilt, pride, resentment, indignation, self-loathing, contempt, etc. would all seem quite out of place when you’re just making a transaction, or just doing or saying what tends to get people to do something you want.

Well, sometimes instead of money, a smile, a tone of voice, or verbal salesmanship, it’s a blow job that gets you what you want. To her, it seems, it’s just a neutral fact of life that many men much of the time respond to something sexual from her in a way that suits her purposes, so she does what she needs to do.

Using sex the ways she does—and her stripping, hooking past—doesn’t seem to have turned her into someone who can’t have more “normal” or “healthy” sex. When she’s with her Indian friend, she’s able to relax and have relationship sex with him just fine.

Though then again, who’s to say that’s not manipulative at some level as well, whether consciously or not? One day she might need a ride, a place to crash, a loan, an alibi, so why not have one more person on her side who’s disposed to help her? It seems like her using her pussy as a bargaining chip hasn’t spilled over into her dating relationship with an equal, but maybe she’s just more subtly using it as a bargaining chip there as well.

The family dynamics are consistently interesting and well handled in this movie. Her brother is something of a milquetoast, seemingly dominated in turn by his sister and his wife, who mostly don’t like each other. But when you think about it, I don’t know that there’s anything all that objectionable or weak about him after all. He’s a nice guy, he’s trying to help his sister while staying on good terms with both her and his wife, yet he’s not just doing everything she wants and irresponsibly letting her walk all over him. He’s a decent human being, and I would say mostly a positive character.

The movie’s complex enough, though, that even as I say that, there’s a whole angle hinted at with their father that maybe indicates a certain weakness in the brother, maybe a guilt about not standing up a certain way and showing some courage when it could have made a difference.

Similarly, the sister-in-law is not just simplistically hostile toward her husband’s sister. There’s a tension there, they take some shots at each other (mostly about the daughter), but her feelings and behavior are more mixed than that.

There’s one exchange between the two sisters-in-law in particular that caught my attention as unusually well done. It’s understated enough that I couldn’t even be a hundred percent sure that it implies what it seems to me to imply. The moment comes and goes and I’m left thinking I now have a little more insight into both characters—the sister-in-law from what she said, and Gyllenhaal from how she parried it—but I don’t know. Maybe the sister-in-law meant nothing, and Gyllenhaal wasn’t subtly responding to it at all. It’s all nuance, and it’s very nicely done.

There’s also a good “a ha” moment with the father. He’s in the movie just enough to give a general idea of the kind of upbringing she probably had, and to see it was the kind of suburban, middle class childhood with a seemingly fairly sane, nice dad, that typically doesn’t produce a stripper in and out of prison for drugs. But then there’s the “a ha” out of nowhere that gives a key clue about the family, and lets you make more sense of things.

I also liked the way that toward the end she gains some insight into parenting, into the difference between loving your child in the abstract and being determined to regain the opportunity to parent her, versus what it takes to parent on a day-to-day basis, where a lot of the mundane challenges don’t fit a fantasy, don’t automatically succumb to a “love conquers all” approach.

Sherrybaby is an intelligent, thought-provoking, well-acted movie from start to finish. It’s far from a fresh idea or fresh milieu—drugs, crime, sex, a sympathetic protagonist trying to get out of the gutter—but if anything that makes it even more of an accomplishment that it impressed me as much as it did. I’d put this in the top 20% of films I’ve written about so far, maybe in the top 10%.


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