Not often do we equate Fyodor Dostoevsky’s concept of Existentialism with comedy, but the truth of it is that the two pair together quite well.

It can be difficult to define yourself as anything short of being a cynic when immersed in the study of human nature and its Existentialism roots. If anything, the development of cynicism for the Existentialist is almost an unavoidable occupational hazard. Look on the bright side though; with an understanding of Existentialism and the divine cynicism responsible for the existential dread we endure on a daily basis, we are bestowed the gift of dry humor. An acquired taste in comedy designed to precisely reflect the jaded and insightful nature of the modern Existentialist, it’s no wonder that we (especially those of us here at VM Productions) retreat to the cool comforts of humor amid the woes of living in a waking world of existential dread.

In the spirit of existential dread, bleak outlooks and dry humor, check out these five cult classic comedy films fit for the challenge of humoring just about any jaded soul.

5 Of Our Favorite Comedies Focused On Dealing With Existential Dread

My First Mister

Easily the single most overlooked film on this surely binge-worthy list, My First Mister starring Albert Brooks (The Simpsons, Finding Dory) and Leelee Sobieski (Eyes Wide Shut, The Wicker Man) is a genuinely dry, awkward and grimly-silly coming-of-age tale. Set within the confines of a hilariously unlikely friendship between a juvenile, but significantly jaded, mall-goth and a short-fused OCD bachelor, My First Mister is a parable on the relationships that we, as humans, form to protect ourselves from the looming threat of existential dread brought forth by being lonely and misunderstood.

From the bleak bottomlessness of existential dread, to the awakening of a newly found optimism, the entertainment value of this film is found not in adventure but in its insight into the human condition and the need to form relationships. Managing to be both bittersweet and cynically hopeful, My First Mister is an enigma even among dark humor flicks and a must-see for fans of any such stylings.

2. Heathers

Heathers is as classic a teen “dramedy” as Clueless but also just as dysfunctional as its sinister sister Jawbreaker. In case this classic somehow slipped through your fingers over the years, Heathers is a stupendously hilarious allegory on struggling to fit in within the confines of conventional society while dealing with the dangers and temptations of such brought on by peer pressure while staying true to yourself. Starring Shannen Doherty (Mallrats, Charmed), Christian Slater (Archer, True Romance) and Winona Ryder (Stranger Things, Edward Scissorhands), Heathers is the perfect hybrid of an aesthetic and puffy-sleeved romantic comedy and a teen slasher.

3. Office Space

Quite possibly the premiere ballad for the 9-5 working stiff, Office Space has earned itself a permanent seat at the metaphorical table for film’s dealing with existentialism in the most viscerally humorous ways possible. Focusing on the trivialities of everything from our daily commute to trying to date in the “working world,” Office Space is an insightful foray into the daily struggles of cubicle dwellers as it is undeniably candid in its humor.

4. American Beauty

A film set for the stage, American Beauty was initially intended as a play before making its way to the silver screen. Focusing on the many facets of human nature such as relationships, sexuality and conformity and the various pressures of maintaining the ideal outward aesthetic, American Beauty manages to be both tragic and hilarious in all of its explorations into human melancholia. With its superb humor and complexity, it’s no wonder this title continues gaining the favor of struggling, workaholic and socially rebellious fans year after year.

5. Clerks

As if the chaos for these lowly convenience store attendants wasn’t enough to ignite a downward spiral of existential dread, writer and director Kevin Smith’s use of black and white perfectly accentuates the daily dose of cynicism his 1994 cult classic retail anthem, Clerks brings. The ironically austere appeal of Clerks dry and raunchy humor launched an empire of similarly humored films to come from Smith including fan favorites with an ever revolving cast like Mallrats and Dogma.

What’s your favorite comedy film dealing with existential dread? Connect with us on Facebook and Twitter and drop us a line telling us what your favorite comedy film is and why!

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