10 Best Hipster Movies of All Time

Updated June 27, 2018
5 min read

How do you classify “what’s a hipster movie?” or simply put “what’s a cool movie”. In my opinion, hipsters usually fall for the films that are about eccentric characters. Also, if the film is intellectually stimulating or weirdly funny, it is given that hipsters would love it. But here’s the most important criteria: the film should make them feel that it is “cool” to be “different” or “weird”. With that said, let’s jump right into the list of best coolest movies. You can stream some of these best hipster movies on Netflix, Hulu or Amazon Prime.

10. The Perks of Being Wallflower

The Perks of Being a Wallflower’ is a coming-of-age tale of an introvert teen, Charlie, who enters high school as freshman and finds difficult to intermingle until he is befriended by two seniors, Sam & Patrick. A friendship that teaches him to be comfortable in his own skin and explore the new dynamism of relationships. The biggest achievement of the film is how beautifully it captures the rich tapestry of growing up experiences soaked in lessons learnt for lifetime. It also shows that every individual in his or her own way is beautiful and worthy.

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9. Donnie Darko

Donnie Darko is a cinematic wonder. It has a grandiose vision with a sprawling imagination of an affluent adolescent. Down to it’s insidiously naughty elements, “Donnie Darko” is about a young rebel “Donnie” who pays odes to the likes of “The Catcher in the Rye” and successfully brings glib humor through intimidating characters and subjects. Donnie is as weird and wonderful as a movie character can get.

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8. Trainspotting

A black comedy about heroin addicts in Scotland made stars of its cast and director, who gives us fast paced, pulse pounding work that makes no judgments on heroin, great when you are on it, hell when you are coming off. The film opens in a fast-paced motion and never seems to be still, the characters are always walking, running, shooting up, just moving all the time. It also manages to somehow make drug addiction seem both the worst and the coolest of things.

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7. The Royal Tenenbaums

‘The Royal Tenenbaums’ is an amalgamation of all of the qualities that we admire Wes Anderson and his films for. It’s is a delightful adult comedy with many quirks and a sense of poignancy. We have always known Wes Anderson for creating these quirky, social misfits but adorable characters but Royal Tenenbaum might be his best creation of all.

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6. Her

The protagonist in the film falls in love with an A.I. Beat that level of weirdness! But seriously speaking, ‘Her’ is easily one of the most imaginative movies ever made. The true worth of ‘Her’ will be realized when the idea (falling in love with an Artificial Intelligence) that it is based upon gets ultimately realized, and whenever that happens in future, I am sure people are going to look back at Her and at Spike Jonze in disbelieved awe on foreseeing the future with such disarming precision.

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5. Almost Famous

Writer and director Cameron Crowe’s experiences as a teenage rock journalist inspired this coming-of-age story about a 15-year-old boy hitting the road with an up-and-coming rock band in the early 1970s. There’s a personal element to the film that you can’t miss. It is warm and fuzzy, but also equally memorable and effective.

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4. Lost in Translation

‘Lost in Translation’ is the single greatest movie ever made about what it feels to feel nothing — or what we commonly refer to as “ennui”. It is about two people who feel unaccepted and misfit in a place they don’t want to be and yet find a way to enjoy that. Based on an exquisitely rich screenplay by Sofia Coppola, the film is a deft balance of humor, poignancy and melancholy.

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3. The Big Lebowski

Well, the “dude”. Need I say more?

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2. Eternal Sunshine of the Spotless Mind

A love story of two weirdos. And it couldn’t have been more beautiful. The dizzying, surreal epiphany of love and heartbreak has never been explored in the manner and to the degree of success with which this film does. Writer Charlie Kaufman and director Michel Gondry have created a film that is not only unique in its own way but also endlessly re-watchable with something new to be found within every viewing.

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1. Fight Club

Very deserving and expected selection for the numero uno position. There’s a reason why it is a cult classic and especially popular among “hipsters”. Within all in its maze of action and eccentricity, ‘Fight Club’ has a core that any socially misfit person not only identifies with but also wants to live by, and that core is about not giving a fu*k about what others think about you.

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