5 Dark Academia Movies to Hold You Over Before ‘The Holdovers’!

If ‘The Holdovers’ hasn’t been released in a theater near you yet, here are some movies to tide you over while you wait!

It’s been nearly 20 years since Alexander Payne and Paul Giamatti collaborated on the Academy Award winning Sideways, and with their new project, The Holdovers, slowly releasing to theaters across America, fans have been getting a craving for dark academia once again.

Something about old buildings, weird rich people drama, and spending more time at school than anyone has ever cared to, really speaks to people and I can’t say I’m any exception. Thus, since The Holdovers hasn’t been released in theaters yet for all, I figured we all deserved a curated dark academia watchlist while we wait.

Kill Your Darlings (2013)

Let me tell you a story about this movie. Until around 2021, I had no clue it existed. My roommate begged me to watch this movie with him, claiming that it was an insane biopic following Alan Ginsburg (a poet I did not know at this point) and I could not think of anything I wanted to watch less. How wrong I was.

I have not forgotten about this movie since I was roped into watching it and for good reason. 2013’s Kill Your Darlings is a ride from beginning to end that routinely likes to wait until the slow parts to remind you just what kind of movie it is. It has everything: murder, scandalous affairs, weird academic rivalries, and it’s all based on a true story. If any of that sounds interesting to you, give it a try. You will not regret it.

You can watch it now on Max or Amazon Prime.

Dead Poets Society (1989)

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O Captain, My Captain– Let’s go ahead and get this one out of the way because it is a true classic of the subgenre and a must-watch for basically any movie lover out there. The only reason it isn’t at the top of this list is that it almost felt too easy to make it first. This film is a true love letter to your favorite English teacher and holds a special place in the hearts of many, especially due to Robin Williams’ life-changing performance.

It is emotionally intelligent, gentle, and yet sharp and impactful when it wants to be. If core memories were a movie, this would be it.

You can watch Dead Poets Society for rent on Amazon Prime, Vudu, and YouTube.

Black Swan (2010)

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Back to our more contemporary entries, Black Swan toes the line between drama and horror in a way that can only be described as disturbing to its core. Following a ballerina named Nina, she is a shoo-in for the prima ballerina in the artistic director’s opening production of “Swan Lake”. However, she becomes intertwined with a new ballerina named Lily and a twisted relationship emerges.

This film very much applies the aesthetics and values of dark academia to a ballet setting and it works beautifully, reflecting the intense relationship between the women and also between Nina and ballet itself. It is a grueling and intense film that hones in on this deep need for perfection that cannot be achieved.

You can watch Black Swan for rent on Amazon Prime, Vudu, and Youtube.

Maurice (1987)

This movie isn’t dark or dramatic, but it gets to you in a profoundly sad way. Initially published as a novel in 1971, Maurice was never released during the author’s (E.M. Forster) lifetime. It was intentionally released posthumously, as Forster believed it would not be worth it to release while male homosexuality remained liable for prosecution in the UK. It’s a painful story that only got a happy ending many years later.

The film itself is a story about the complexities of love and being queer in a time that made little space for the existence of such people. It is about a man on a journey to accept himself and it is a story best experienced without a great deal of explanation. I encourage you all to seek out this movie and continue to give E.M. Forster’s story the attention it deserves. Also, a young Hugh Grant is there, if that’s any further motivation.

You can watch it for free now on Tubi or on Amazon Prime.

Cruel Intentions (1999)

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Sometimes movies can just be about very talented actresses playing weird psychosexual mind games and that’s okay because at the very least you’re gonna have a good time and it will be exceedingly 90s. Cruel Intentions (starring Sarah Michelle Gellar and Reese Witherspoon) is what you might generously call a weird film, as it follows a woman named Annette who becomes involved in a weird scheme between another woman, Kathryn, and her boyfriend, Sebastian, as she writes an article for Seventeen Magazine about staying pure for marriage with her boyfriend.

Got all that? Great. Glad we’re all on the same page because that’s as much as I can explain without it getting entirely out of hand. It’s got everything Kill Your Darlings has with the cheese of the 90s. This is a movie made for people with a revenge fantasy, but also no one in this movie is a good person.

You can watch it now for free on Tubi and Plex.