Ben Stiller is perhaps greatest recognized for broad comedic roles in hits like Zoolander and Meet the Dad and mom, however beneath the mainstream laughs lies a filmmaker drawn to darker, extra introspective themes. Transitioning easily from actor to acclaimed director, Stiller’s tasks ceaselessly grapple with isolation, id crises, and societal pressures. He skillfully merges unsettling parts with comedic timing, creating tasks that really feel each acquainted and disquietingly unusual.

Severance
- Launch Date
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February 18, 2022
- Showrunner
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Dan Erickson, Mark Friedman
Followers captivated by the uneasy rigidity of Severance will discover related vibes in Stiller’s various physique of labor. From the grim but fascinating jail break drama Escape at Dannemora to the surreal melancholy of The Secret Lifetime of Walter Mitty, these movies and exhibits exemplify Stiller’s present for crafting tales that unsettle as a lot as they entertain.
10
‘Escape at Dannemora’ (2018)
A stark departure from Ben Stiller’s comedic roots, Escape at Dannemora is a harrowing, slow-burn crime drama based mostly on the true story of a 2015 jail break in upstate New York. The collection follows two convicted murderers, Richard Matt (Benicio del Toro) and David Sweat (Paul Dano), who manipulate a lonely jail worker, Tilly Mitchell (Patricia Arquette), into aiding their elaborate escape. Stiller directs all seven episodes with a meticulous, virtually medical consideration to element, capturing the claustrophobic monotony of jail life whereas slowly unraveling the complicated, typically disturbing relationships between the important thing gamers.
Stiller’s Directorial Evolution into Psychological Darkness
Whereas Escape at Dannemora lacks the overt surrealism of Severance, it shares the identical eerie sense of entrapment, each bodily and psychologically. Stiller’s path leans right into a grounded, procedural fashion, however beneath the realism lies an undercurrent of dread. His means to extract layered performances—significantly from Arquette, whose portrayal of Tilly is each pathetic and terrifying—proves his directorial energy in navigating morally murky territory. Very like Severance, the collection explores themes of management, manipulation, and the phantasm of freedom, making it a must-watch for followers of unsettling, slow-building rigidity.

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9
‘The Secret Lifetime of Walter Mitty’ (2013)
A visually gorgeous and deeply introspective adaptation of James Thurber’s quick story, The Secret Lifetime of Walter Mitty follows the mundane existence of Walter (Ben Stiller), a timid, daydreaming picture editor who embarks on a real-life journey to trace down a lacking {photograph}. Whereas the movie initially presents itself as an uplifting journey of self-discovery, there’s an underlying melancholy that provides Walter’s escapism a bittersweet edge. His vivid fantasy sequences—at occasions humorous, at occasions surreal—blur the road between creativeness and actuality, creating an environment that feels each inspiring and unnerving.
Fantasy as a Double-Edged Sword
Very like Severance, Walter Mitty explores themes of dissociation, id, and the methods by which we assemble alternate realities to flee dissatisfaction. Stiller’s efficiency is restrained, letting Walter’s loneliness seep via the grand journey. His path, in the meantime, leans into dreamlike visuals, emphasizing huge, empty landscapes that replicate Walter’s inside void. The movie’s existential undercurrent aligns with Severance’s depiction of compartmentalized lives—each protagonists wrestle with the dissonance between their imagined potential and their lived actuality. Whereas Walter Mitty finally leans extra optimistic, it nonetheless carries the identical eerie sensation of watching somebody get up from an extended, self-imposed sleep.
8
‘Actuality Bites’ (1994)
A defining movie of Nineteen Nineties Gen X cynicism, Actuality Bites captures the aimless, post-college drift of a gaggle of pals navigating love, work, and id in an more and more company world. Directed by Ben Stiller, the movie follows aspiring documentary filmmaker Lelaina (Winona Ryder), her sarcastic greatest pal Troy (Ethan Hawke), and her well-meaning however out-of-touch boyfriend Michael (performed by Stiller himself). Whereas marketed as a romantic dramedy, Actuality Bites carries an underlying bleakness—its characters teeter between idealism and nihilism, their relationships strained by the very techniques they declare to reject.
A Much less Overtly Sci-Fi Severance
Although Actuality Bites lacks the overt style parts of Severance, it resonates in its critique of company tradition and the soul-crushing compromises maturity calls for.
Stiller’s character, Michael, represents the seduction of assimilation—he’s a well-meaning however clueless government who tries to package deal Lelaina’s uncooked, genuine documentary into one thing marketable. His presence highlights one in every of Severance’s core tensions: the wrestle between private authenticity and the machine-like grind of capitalism. The movie’s existential undertones, mixed with Stiller’s means to steadiness humor with discomfort, make it an early precursor to the themes he would later discover extra absolutely in Severance.

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7
‘Everlasting Midnight’ (1998)

Everlasting Midnight
- Launch Date
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September 16, 1998
- Runtime
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88 minutes
- Director
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David Veloz
A uncooked, unsettling dive into dependancy and self-destruction, Everlasting Midnight stars Ben Stiller in a uncommon dramatic position as Jerry Stahl, a proficient but deeply troubled tv author whose success is overshadowed by his heroin dependancy. Primarily based on Stahl’s memoir, the movie unflinchingly portrays the contradictions of Hollywood—the place artistic brilliance typically coexists with private wreck. Stiller’s efficiency is way from his normal comedic persona; his Jerry is charming and quick-witted, but hollowed out by his personal compulsions. The movie strikes via flashbacks and surreal, drug-fueled sequences, making a fragmented, disorienting ambiance that mirrors Stahl’s fractured psyche.
Stiller’s Darkest Position Earlier than Severance
Like Severance, Everlasting Midnight explores themes of duality—the rigorously managed public persona versus the chaos beneath. Stiller’s Jerry is trapped in a cycle of self-sabotage, very similar to the Lumon staff who unknowingly suppress their worst impulses for company effectivity. His efficiency is haunting in its restraint, proving that lengthy earlier than Severance, Stiller was drawn to tales about isolation, dependancy to routine, and the existential dread of being consumed by one thing past one’s management. Should you’re in search of one other Stiller challenge that leans into psychological misery and eerie introspection, Everlasting Midnight is a vital, unsettling watch.
6
‘The Cable Man’ (1996)

The Cable Man
- Launch Date
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June 10, 1996
- Runtime
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96 Minutes
On the floor, The Cable Man seems to be like a typical ‘90s comedy, however beneath its slapstick and absurdity lies one thing far darker. The movie follows Steven (Matthew Broderick), a mild-mannered man who makes the error of befriending an overzealous cable installer, Chip (Jim Carrey). What begins as a innocent friendship spirals into an obsessive, psychological nightmare as Chip inserts himself additional into Steven’s life, revealing a deep loneliness and emotional instability that turns comedic desperation into one thing genuinely unnerving. Stiller directed the movie, leaning into its uncomfortable rigidity and foreshadowing his later means to combine humor with unease.
Social Isolation and the Risks of Synthetic Connection
Like Severance, The Cable Man explores loneliness in a hyper-connected world. Chip’s obsession with tv as a surrogate for actual human interplay feels eerily prophetic—lengthy earlier than the web and social media, the movie examined how media consumption may distort somebody’s sense of actuality. Stiller’s path heightens the movie’s eerie high quality, utilizing stark lighting, voyeuristic framing, and an off-kilter comedic tone that retains the viewers on edge. Whereas marketed as a broad comedy, The Cable Man is a deeply unsettling take a look at emotional dependency and the way isolation breeds desperation—an concept Severance takes to its personal excessive.

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5
‘Greenberg’ (2010)

Greenberg
- Launch Date
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March 26, 2010
- Runtime
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107 Minutes
A deeply uncomfortable character examine, Greenberg follows Roger Greenberg (Ben Stiller), a failed musician who returns to Los Angeles to house-sit for his brother whereas aimlessly making an attempt to rebuild his life. Greenberg is bitter, aimless, and unable to attach with the individuals round him—together with Florence (Greta Gerwig), his brother’s assistant, who turns into an surprising emotional tether. Directed by Noah Baumbach, the movie is an train in restrained awkwardness, forcing the viewers to take a seat within the discomfort of Greenberg’s self-imposed isolation and his incapability to operate in a world that has seemingly left him behind.
A Portrait of Self-Sabotage
If Severance explores the suppression of feelings in favor of company effectivity, Greenberg is the inverse—an unfiltered take a look at a person whose unchecked neuroses make him virtually unattainable to be round. Stiller’s efficiency is brilliantly uncomfortable, stripping away any likability in favor of uncooked honesty. Like Mark Scout in Severance, Greenberg is a person caught in emotional limbo, unwilling or unable to maneuver ahead. The movie’s melancholic tone, mixed with Stiller’s refined but devastating efficiency, makes it the most effective precursors to Severance’s exploration of id, loneliness, and existential inertia.
4
‘Zoolander 2’ (2016)

Zoolander 2
- Launch Date
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February 12, 2016
- Runtime
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102 Minutes
Whereas the unique Zoolander (2001) was a goofy satire of the style trade, its 2016 sequel takes a flip into unexpectedly darker, surrealist territory. Zoolander 2 follows Derek Zoolander (Ben Stiller) and his former rival-turned-friend Hansel (Owen Wilson) as they’re pulled again into the high-fashion world, solely to search out themselves entangled in a weird conspiracy involving assassinations, secret societies, and a plot that stretches past the same old bounds of parody. The humor leans extra sinister, with exaggerated violence, grotesque physique horror (like Will Ferrell’s Mugatu present process nightmarish beauty surgical procedures), and a nihilistic edge that makes it really feel extra unsettling than its predecessor.
Absurdism with a Sinister Streak
Stiller’s Zoolander 2 aligns with Severance in the best way it takes a heightened, corporate-driven world and exposes its dystopian underbelly. Whereas Zoolander performed as a self-aware spoof of vainness and superstar tradition, Zoolander 2 leans into an eerie world the place characters usually are not simply exaggerated however trapped in their very own self-parodies. Derek, as soon as the last word himbo, now grapples with irrelevance, isolation, and the surreal horror of being a relic in an trade that discards individuals as rapidly because it glorifies them. Although the movie is commonly absurd, it has moments of uncanny bleakness—virtually as if Severance’s company detachment was repackaged in high-fashion absurdity.

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3
‘Duplex’ (2003)

duplex
- Launch Date
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September 26, 2003
- Runtime
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89
- Writers
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Larry Doyle
At first look, Duplex seems to be a lighthearted comedy about an formidable younger couple making an attempt to safe their dream residence. However because the movie unfolds, its tone veers into darkly comedic horror. Ben Stiller and Drew Barrymore star as Alex and Nancy, a pair who purchase what looks like the right Brooklyn brownstone—aside from one downside: their upstairs tenant, Mrs. Connelly (Eileen Essell), an aged lady whose seemingly innocent presence escalates into full-blown psychological warfare. As they desperately attempt to take away her, the movie morphs from a unusual comedy right into a nightmare about actual property, entitlement, and ethical decay.
Stiller because the Everyman on the Brink of Insanity
Very like Severance, Duplex faucets into a secular scenario—proudly owning property—and warps it into one thing terrifying. Stiller’s Alex begins as a well-meaning husband however steadily unravels, pushed to irrational extremes as his dream of homeownership turns right into a dwelling nightmare. His gradual descent mirrors the type of psychological breakdown seen in Severance, the place characters wrestle to reconcile their perceived management with their precise helplessness. The movie’s humor is more and more uncomfortable, forcing the viewers to chortle whereas watching two individuals lose their grip on sanity—a signature component of Stiller’s darker comedies.
2
‘Flirting with Catastrophe’ (1996)

Flirting with Catastrophe
- Launch Date
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March 22, 1996
- Runtime
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92 minutes
- Director
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David O. Russell
David O. Russell’s Flirting with Catastrophe follows Ben Stiller’s character, Mel Coplin, as he embarks on a chaotic street journey to trace down his organic dad and mom. Not too long ago married and a brand new father, Mel is determined to resolve his personal id disaster earlier than absolutely getting into maturity. What begins as a easy quest spirals into an off-kilter odyssey of miscommunication, misunderstandings, and deeply dysfunctional household dynamics, all wrapped in an more and more surreal ambiance.
A Man Shedding Management of His Personal Narrative
Whereas Flirting with Catastrophe is extra rooted in farce than outright psychological horror, it shares Severance’s fascination with id and the absurdity of making an attempt to reclaim one’s personal life. Stiller’s Mel is each a information and a sufferer of the chaos round him—he’s looking for readability however as an alternative finds himself tangled in weird, unplanned detours that strip him of any sense of management. The movie’s sharp, neurotic vitality mirrors Severance’s depiction of people trapped by bigger forces, desperately making an attempt to make sense of a world that refuses to play by logical guidelines.
1
‘Brad’s Standing’ (2017)

Brad’s Standing
- Launch Date
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September 15, 2017
- Runtime
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101 minutes
Brad’s Standing is an introspective, anxiety-laden character examine that follows Brad Sloan (Ben Stiller), a middle-aged man grappling with emotions of inadequacy as he accompanies his teenage son on a school tour. Regardless of dwelling a snug life, Brad turns into consumed by comparisons to his extra outwardly profitable faculty pals, spiraling into an existential disaster fueled by envy and self-doubt. Director Mike White (The White Lotus) infuses the movie with a subdued, virtually suffocating tone, making Brad’s interior turmoil really feel as isolating as it’s relatable.
A Man Unraveling in Actual Time
Like Severance’s Mark Scout, Brad is a person trapped in his personal thoughts, unable to reconcile his current actuality with the life he as soon as imagined for himself. Stiller’s efficiency is each subdued and painfully uncooked—removed from his broader comedic roles, he performs Brad with a quiet desperation that makes his inside monologue really feel virtually intrusive.
The movie’s themes of id, remorse, and self-imposed isolation parallel Severance’s exploration of compartmentalized lives, the place notion and actuality are consistently at odds. Whereas Brad’s Standing doesn’t enterprise into dystopian horror, its deep sense of existential unease makes it one in every of Stiller’s most thematically resonant movies for followers of Severance’s model of melancholic self-exploration.