Mary Stuart Masterson's gayness is barely a secret.
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It’s rumored that 1987's Some Kind Of Wonderful exists only because John Hughes was pissed off about Pretty In Pink. If Hughes had his way, Duckie and Andie, the best friends from the TBS staple, would've ended up together in the end. But since test audiences didn't like that and instead wanted Andie to end up with the decidedly less-gay-seeming yuppie Blaine, that ending was produced. As retaliation Hughes made Some Kind Of Wonderful the next year, which is basically the same exact movie but with the genders of all the characters reversed. Now he could have the ending he wanted all along.
In Some Kind Of Wonderful, Watts (constant lesbian-in-hiding Mary Stuart Masterson) is cast in the Duckie role, playing the badass best friend to protagonist and Andie 2.0 character, Keith (Eric Stoltz, who tragically has far fewer colorful lace vests than Molly Ringwald in Pretty In Pink).
Even though I don't believe it was intentional on Hughes' part, in both movies the fantastically cool but overlooked best friend is super, super gay. And while it would be awesome if the fantastically cool but overlooked best friend was believably straight and thus a plausible romantic option for our intended hero, this isn't the case in either movie, as evidenced in this photo which may as well be a still from an Indigo Girls music video.
There's even a scene in Some Kind Of Wonderful where the tough biker guy who constantly harasses and therefore is probably way into Watts, tells her she must be a lesbian and of course, it's supposed to be a #MajorBurn. So, it totally makes sense that even if she was (and she was) gay, she was closeted. If you were already getting shit for being a presumed lesbian in 1987, imagine how much more you'd get if you were a confirmed lesbian. Probably (sadly) not worth the trouble.
Now before you can say it, I want to acknowledge that, as in all Secretly Gay Movies, it's completely possible to have a character like Watts who is straight as an arrow and simply enjoys dressing like she just walked out of a 1992 San Francisco leather bar. Secretly Gay Movies is oftentimes just as aspirational as it is observational.
However let’s consider the evidence for Watts’ Sapphic side. First of all, she goes by her last name. How butch is that. Secondly, there is the hair. Sure, straight girls can rock a pixie cut, but a short haircut like that and a leather motorcycle jacket reads more Jenny Shimizu than Mia Farrow. Also, Watts plays the drums. Her character is basically defined by this hobby. Is there any instrument more lady gay than the drums? Not even an acoustic guitar at the Michigan Womyn’s Festival is more gay than the drums. So other than Watts constantly drumming on things, wearing lots of mandarin collars, and some of the best secondhand leather vests money can buy, we can just assume that Watts has a closet full of flannel (the official lesbian sigil) even though we never actually see her wear it.
The entire plot of Some Kind Of Wonderful is based around a love triangle between Keith, Watts, and Amanda Jones. That's right. The Amanda Jones. The girl so cool that she has her own song that is basically her name repeated a million times. But the question really becomes, how is this a love triangle exactly? Is it "Who gets Keith?" or "Keith, Watts, and which one of us is more into girls?'"
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I'm not suggesting that Watts was into Amanda Jones herself – she probably had a jones on for Ally Sheedy in The Breakfast Club – but I will say this conversation happens when Keith first admits he's kind of into Amanda. (Note: I took some liberties for our amusement.)
Keith: What do you think about Amanda Jones?
Watts: (pauses, thinks about how hot girls are, thinks about how she'll get her ass kicked for thinking about how hot girls are) …rat bait, why?
Keith: Just curious.
Watts: What about? Like, being gay? I'm curious about that all the time. It doesn't mean you have to do anything about it. Wait, what was the question again?
Keith: Her, who she is.
Watts: Because she's beautiful, right? Guys are so sickening. Really it must be a drag to be a slave to the male sex drive. Fortunately, I couldn't care less about the male sex drive.
Keith: I didn't say anything about sex.
Watts: (sarcastic) Oh, you wanna start a book club with her?
Book club formation is one of the primary forms of lesbian foreplay. You both start reading Virginia Woolf and next thing you know you are married. It's a thing, I swear. I read about it at a lesbian book club.
The movie is full of moments like this including
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And this part, where Watts is helping Keith practice his kissing skills so he'll be really good at kissing girls and so will she.
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Is there anything conclusive about whether or not Watts was gay? Sure, she ended up with Keith in the end, but plenty of lesbians date guys in high school and then realize “Oh this is a bad idea primarily because I am a homo,” enroll in an all-girl liberal arts college where they make Ani DiFranco mix tapes, played drums in a riot grrl band, and date girls who dress like Edie Brickell. A decidedly better fate.
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