Oh, Dear God, It's March Again: Essential Movies About Existential Despair [Please Help!]

The Swimmer
As far as films about the promise of American midcentury life go, “The Swimmer” is a doozy. It’s based on a beautiful New Yorker short story by John Cheever, who was an expert at profiling the multifarious nature of human sorrow. The Technicolor film adaptation, directed by Frank Perry (“Diary of a Mad Housewife,” the Joan Didion-penned “Play It As It Lays”) with some uncredited help from a then-ascendant Sydney Pollack, manages to build off and improve upon the source material, mercilessly poking holes through the flimsy façade of 1960s suburban bliss. Burt Lancaster gives one of his most memorable performances here as virile suburbanite Ned Merrill, and he’s assisted by “3 Women” actress Janice Rule, as well as Joan Rivers in her film debut. “The Swimmer” is a film of pool parties and subtly unsettling personal exchanges, one that only grows stranger and more alluring as it builds towards its memorably provocative conclusion. – NL

“Synecdoche, New York”
Charlie Kaufman’s sprawling directorial debut, “Synecdoche, New York,is an overwhelming film. This isn’t Kaufman in the quasi-humanist mode that won him acclaim with films like “Adaptation” and “Eternal Sunshine of the Spotless Mind,this is Charlie Kaufman: Full Throttle. “Synecdoche” might feel like a cinematic therapy session, but it’s also one of the most thematically ambitious directorial debuts you’re ever likely to see. Much like the ever-evolving play at the center of the film, penned by Caden Cotard (the maddeningly brilliant Philip Seymour Hoffman), Kaufman’s debut is about the never-ending cycle of existence and our quest for a place in the chaos of it all. Even when we feel like we’re finally on the right track, our lives can still feel meaningless; our purpose, ultimately unclear. Like Kaufman, Caden is praised as a genius, but his genius is tragically undercut by his own deep-seated fears of inadequacy and the notion that he’s simply watching life pass him by. Caden is constantly searching for meaning in his life, yet by the end, he’s missed out on an entire lifetime of meaningful relationships and interactions that he never truly experienced because he was so preoccupied with obsessively analyzing his own misery. It might be his most polarizing film to date, but only Charlie Kaufman could make something as simultaneously bleak and life-affirming as “Synecdoche, New York.” – MR

Through A Glass Darkly
Couldn’t all of Ingmar Bergman’s movies said to be about existential despair (and most of Antonioni’s at that?)? Sure, but few of the Swedish maestro’s works are as openly fascinated with that topic as “Through a Glass Darkly,” which was originally conceived as a three-act stage play. “Glass Darkly,” although it’s still a relatively early film in this director’s filmography, often plays like a game of Ingmar Bergman bingo. A remote island as a primary location? Check. Psychosexual hang-ups and tortured spiritual inquiry? Double check. Dreamlike harbingers of spiders? Better check that one off too. The film unfolds over the course of a single day, exploring tough topics such as mental illness, the absence of God, and the parasitic inclination that certain writers suffer from when they mine their own family misfortunes for “material.” Like all of Bergman’s films, “Glass Darkly” rejects passive viewing: it’s an unflinching interrogation of humanity’s darkest impulses. – NL

“Wendy and Lucy”
Few directors are as adept at depicting American poverty as Kelly Reichardt, as proven by her lo-fi masterpiece “Wendy and Lucy.” Over the course of 80 minutes, Reichardt shows us the economic plight of the modern American through the eyes of a drifter named Wendy (Michelle Williams, in her best performance) and her companion, a dog named Lucy. Reichardt is portraying an entire generation defined by economic peril, and she does it mostly through wordless interactions, beautifully ruinous imagery, and a central performance that will break your heart. There’s remarkable restraint in Reichardt’s approach that puts her in a class of her own, but it’s rarely been put to better use. “Wendy and Lucy” also benefits immensely from the power of silence. The hurricane of emotions Reichardt leaves you grappling with in the film’s final moments never feels manipulative because the preceding 70 minutes offer such a sensitive understanding of the trauma of being poor in America. Reichardt’s masterwork hits even closer to home a decade-plus after its release, particularly as we look down the barrel of another financial crisis that will only further punish the most economically impoverished citizens in the wealthiest country on Earth. – MR

Honorable Mentions:
So the reality is, in cobbling this piece together, we found enough films about existential despair to fill several lists. For now, we’ll have to consign some of these very exciting and worthwhile movies to our Honorable Mentions section, where we pay respect to the outstanding works that almost made the cut.

Spike Jonze has directed a pair of brilliant dark comedies about the terror of our 21st-century existential condition and while we mention most Charlie Kaufman films, “Being John Malkovich,” there is a Kafka-esque comedic existential despair at its center too. Haneke’s “Amour” is not so overtly about despair of the existential variety, but it’s nevertheless an uncharacteristically touching and yet beautifully unsentimental look at the decay that comes with old age. We would be remiss for not including the great “Bitter Tears of Petra Von Kant” here, and ditto for Nicolas Roeg’s masterpiece of sensory dislocation and sexual ennui, “Don’t Look Now.” 

Fight Club” is an important Gen X despair movie that’s not typically as depressed about things: an acidic satirical thriller about a generation raised on false promises and a proverbial bill of goods. Gus Van Sant’sGerry” strips the very ethos of despair down to its most bare-bones incarnation, resulting in one of the experimental indie icon’s most pared-down works. “Dead Man,” Jim Jarmusch’s glorious, psychedelic anti-Western, is very much concerned with our mortal human shells, and what happens when our immortal souls vacate those shells. 2017’s “A Ghost Story” is another excellent entry in this subcategory, enough so that less patient viewers can grit their teeth through that sensationally long take where Rooney Mara grief-binges an entire pie in the aftermath of her lover’s death.

Paolo Sorrentino’sThe Great Beauty” was one that almost made its way onto this list, and was narrowly edged out; it’s certainly one of the raunchiest and most uninhibited movies ever made about crippling spiritual emptiness. “Lost in Translation” and arguably several Sophia Coppola movies, and their examination of teen female isolation, also fits the bill here, as does the Coen Brothers’ massively underrated, seductively aberrant period neo-noir, “The Man Who Wasn’t There.” Jonathan Demme’s Ibsen love letter “A Master Builder” offers some remarkable wisdom in regards to what it means to live a full, examined life, and the Mike Leigh classic “Naked” is as despairing a movie as we’ve ever seen though it probably is more apt on a list about nihilism. The mood of Abel Ferrara’sNew Rose Hotel” is one that’s suffused with deep existential malaise; the same is true of “A Pigeon Sat On A Branch Reflecting On Existence.”

Tarkovsky’s “The Sacrifice” is the master filmmaker’s final statement on the human condition, and does deserve a spot on the list, but we’ve got the somewhat similar Bresson pick on the list and it gets at least a cursory shout-out here. Martin Scorsese’s 2016 passion project “Silence” is another entry that merited inclusion, primarily for its stinging observations about the limits of religious sacrifice. Tarkovsky’s mesmerizing “Stalker” seemed like an obvious choice (maybe too obvious), and let’s not forget “The Truman Show,” which prophesized our reality TV-obsessed culture in ways no one could have seen coming. 

Let’s see… there’s also “Vanilla Sky,” which is without a doubt the most despairing movie ever directed by the otherwise cheery Cameron Crowe (we suppose we could say the same thing for “Waking Life” in regards to Richard Linklater). And last but not least, the magnificent, openhearted celestial parable “Wings of Desire,” which we ultimately decided to swap for the more on-brand and ultimately much more depressing “Paris, Texas.”

Stay safe out there, readers, do whatever you need to enable self-care and, as always, thank you for reading.