Sorority Boys: An Accidentally Graceful Look at Womanhood and the Trans Experience

Harmony Colangelo
8 min readJan 12, 2020


The year is 2002. An innocent eleven-year-old walks through their local Drug Mart video section looking for a movie to rent over the weekend when cover art showing three men in not-at-all passing drag catches their attention. The title read Sorority Boys and I HAD to watch it. It was to the point of begging my mother to let me rent it (because it was R-rated) but she caved and rented the film. Not for me, but for us.

I was allowed to get it, but only if she watched it with me. How my rather prude mother did not turn it off 5 minutes in when frat boys were slingshotting dildos across the college campus, I will never know. She did, however, ask if I knew what the dildos were. As I think back as an adult, I want to blame the picture quality of a 20+ year old television and non-flesh toned phallics for why I assumed they were launching balloon animal water balloons. But the more I think about it, it was probably just because I was a pre-pubescent, untainted, chubby cherub. Seeing my first sex toys was not what stuck with after all these years, it was seeing men in women’s clothing for the first time broadcast so blatantly like this. This wasn’t Bugs Bunny trying to trick Elmer Fudd in a bit that lasted ten seconds. This was front and center. These were real life people. This was something that I didn’t know was actually possible.

As is probably the case with most eleven year olds, you can’t fully account for taste because you haven’t had time to refine your palate, and sometimes the stuff you cherish as a kid is some absolute garbage. Maybe you only got one video game for Christmas, so you appreciate it no matter how shallow or repetitive it is, because it’s the only game you are going to get for at least six months. (I am looking you Buck Bumble for the Nintendo 64!) Maybe you learned all of the songs from the first nine Now That’s What I Call Music albums even if you didn’t enjoy upwards of 70 percent of the tracks because you want to listen to music but don’t know where to find music that sounds good to you yet, so you settle for “It’s My Life” by Bon Jovi being one of the more anti-authority things you’d ever heard because you hadn’t discovered punk yet.

Or JUST MAYBE a gross-out comedy about three crossdressing college frat boys opens up a world of possibilities for your life because any sort of transgender representation was such a luxury in 2002 that this felt like it something that had never happened before in the eyes of a dorky, eleven year old kid from Ohio.

Now, I’m not foolish enough to think that just because I have an appreciation for a film like Sorority Boys that it should be featured in college gender studies classes or anything of the sort. It didn’t do anything particularly groundbreaking and as far as its exploration of gender goes, this movie reads more like all of those articles written by “nice” guys with clickbait subtitles like “I pretended to be a woman on a dating site for a week to see what it was like and realized just how badly men treat women. This is what I found…” because apparently people would rather listen to the very short term experience of some guy rather than the day to day perspective of any woman.

THAT SAID, this movie is good natured enough that it does actually handle its topics with some level of esteem that deserves at least some recognition, albeit as more of a peer to films like Juwanna Mann than it is to Tootsie.

So what does Sorority Boys do right that makes it worth analyzing outside of some very specific nostalgia for a once budding trans lass? Let’s start by discussing the plot: Dave, Adam, and Doofer (played respectively by Barry Watson, Michael Rosenbaum, and Harland Williams, the latter of which does the best acting of his career in this film… for what that’s worth) are popular brothers at their fraternity Kappa Omicron Kappa, or the oooh so cleverly named KOK house.

Through internal KOK collusion, they are framed for stealing the annual KOK-tail cruise fundraiser money and kicked out of the frat house. Doofer comes up with a plan for them to dress as women to sneak back in the house to get a tape (that only exists because Adam illegally records his sexual encounters without the consent of his partners) that could prove their innocence, meanwhile, end up living at the Delta Omicron Gamma (DOG) sorority as their plan takes form.

From there it’s a lot of typical “men pretending to be women/fish out of water” scenarios, but the main three each have specific arcs. Doofer/Roberta becomes a pseudo house mother and confidant for the girls of the DOG house, Dave/Daisy develops feelings for the incessantly political house leader Leah which becomes a gender fucked lesbian mess, and Adam/Adina learns to not be such a fuckboi by navigating going from being the big man on campus to becoming “unattractive” and constantly being harassed for having a big ass (oh how beauty standards have changed since the early 2000’s).

Although it’s supposed to be “just for laughs,” one of the better aspects of the film is watching these alpha male frat boys embrace their roles as women, even if they know it’s temporary. They may try to maintain macho posturing only to impress each other, but after a while, they stop making fun of each other and settle into their new personalities. They get excited that a bag matches their shoes, discuss the function and fashion of high heels, and even call each other pretty.

Maybe this is just me reaching and reading more into something than it ever needs to be, but this particular take on dismantling toxic masculinity is very refreshing. I am not saying this is how men should be getting in touch with their “feminine side” but if they (and everyone honestly) stopped roasting each other for not perfectly fitting the mold that they think they should fit in, I’m sure we’d get along better by removing that fear and hostility from our social lives. Crossdressing, trans, or female subjects all aside, having men simply supporting each other and allowing themselves to be vulnerable as a core aspect of a film’s plot was a rarity until bromance films became common a few years later.

The complications of navigating growing feelings for someone while in disguise is a common trope dating back to Shakespearean times but it is atypical to see those conflicting feelings explored while that person is in and out of disguise. This makes the perceived lesbian relationship between Daisy and Leah unique, especially after they end up together at the end of the film after Leah learns that Daisy is Dave. Suddenly, the guy that she thought was only taking women’s studies to skeeve on women and the sweet girl from Minnesota that caused her to question her own sexuality turn out to be the same person. It is a more sincere look at the phrase “love knows no gender” than that found in a lot of more acclaimed (and probably much better) queer romance plots. It’s certainly not perfect or done that well, but this is a scenario I appreciate seeing.

If we are going to explore gender and sexuality, then let’s crack it open and make a mess if we need to. In 2019, when the singular “they” was named Word of the Year by Webster’s Dictionary, let’s screw around with gender and love more. I want to see a pre-transition trans person who’s partner loves them before and AFTER they transition, but films like that simply don’t exist or do that. Sorority Boys isn’t that story either but in a weird way, this is the closest we may have with maybe the only exception being Dog Day Afternoon which treats it’s trans topic as a surprise twist at the end rather than a focal point to the story, something that films like Sleepaway Camp are criticized for.

Sorority Boys is not a “good” movie. It is not trying to say anything important or have an enduring legacy yet it somehow accidentally does. The primary conflict of this film stems from women being seen as inferior because they aren’t fuckable. Cis or trans, in this movie or real life, that is a big, ugly reason why society treats women the way they do. Studies for years have shown that people are nicer to those they find attractive and the prospect of someone, anyone, having even the illusion that they could get laid makes them nicer and basic respect gets stripped if that fantasy ends. All too many times in my life I have been on the receiving end a conversations that shifted from “you’re beautiful and I want to take you out sometime” to “fuck you. You’re ugly. I hope you go die” just because I said I wasn’t interested. This mindset is what this entire film is set around.

Ultimately, what I think I value the most in this film is that it isn’t trying to be perfect. Queer films by queer folks will nearly always be better then straight people trying to tell stories that aren’t theirs. Sorority Boys is queer in the sense that it has straight actors playing straight characters who spend most of the film crossdressing soooo… it straight up isn’t queer.

LGBTQ+ folx always want more representation (myself included) but because of respectability politics, any film that doesn’t present the community in a squeaky-clean light is blasted. Not every queer person is tidy or a “good example of the community” and not every queer story should be presented as such. The “we’re just like you!” belief is damning and dangerous, because assimilation is not always the answer. Our lives ARE different, and it’s okay to acknowledge that. I would rather see a sloppy, straight film that I can salvage positive examples from because it has some interesting angles, over another bland drama that goes through all of the “proper” motions that perpetuate stereotypes and tired-ass storylines.

For the case of Sorority Boys in the vast ethos of trans films, it’s not great representation but it is like looking at a JPEG quality picture taken with a turn of the millennium Canon digital camera for what that era looked like for trans representation in media. It’s not high quality but makes sense for when and where it took place. We as a community should remember the past, good or bad, because that is how we see what experiences we have covered in the past, and how we can improve on them with better representation moving forward.