Dark times call for dark comedies. These 34 films look at life’s bleaker moments and shine a light on the funny parts.

The 34 best dark comedies of all time

Dark times call for dark comedies. These 34 films look at life’s bleaker moments and shine a light on the funny parts.

By Debby Wolfinsohn

and Ilana Gordon

Ilana Gordon is an entertainment, culture, and comedy writer originally from Connecticut. She currently lives in Los Angeles.

EW's editorial guidelines

on August 26, 2026 11:10 a.m. ET

Traditional joke math suggests that tragedy + time = comedy. The 34 films on this list don’t follow this formula, though, because dark comedy isn’t about making comedy comfortable for everybody — it’s about using humor to create comfort for the sometimes niche audience that needs to see it. A film about a grieving family (*The Royal Tenenbaums*) might seem in poor taste to some; to others, it might be the only thing saving them from their own grief.

If your coping mechanism for tough times is laughter, then this is the list for you. These 34 comedies streaming across the internet satirize global issues like nuclear war, cultural trends like beauty pageants, and leave no stone unturned in their quest to make life’s toughest stuff more emotionally palatable.

Keep reading for **‘s list of the 34 best dark comedies of all time, and remember: It’s okay to laugh.**

I Love You to Death (1990)

Miriam Margolyes as Joey’s Mother and Kevin Kline as Joey Boca in ‘I Love You to Death’.

TriStar Pictures/Everett

Serve spaghetti (with a killer sauce) for this one, folks, because marinara is the preferred vehicle for poison in this very Italian true-crime romp. Black? Pitch, because it’s about, ya know, an actual plot to kill an actual philandering husband (played by Kevin Kline in his prime). Based on the wild tale of a real woman (Frances Toto) and her multiple attempts to off her cheating spouse, Tracey Ullman plays the jilted wife with aplomb. Espresso-dark and over the top (with an amazing cast including Keanu Reeves and River Phoenix), the real story is crazier than fiction, but you won’t find any spoilers here. *—Debby Wolfinsohn*

Where to watch *I Love You to Death*: Amazon Prime Video (to rent)

Better Off Dead (1985)

John Cusack as Lane Meyer in ‘Better Off Dead’.

So much to love here: a baby-faced John Cusack, quotable lines (“I want my two dollars!” “Gee, I’m real sorry your mom blew up, Ricky.” ), random cartoon moments, Curtis Armstrong (*Revenge of the Nerds’* Booger!) skiing in a top hat, goofball humor (dinner literally crawls off the plate), and because this is a dark comedy, a running “I’m going to kill myself” plotline that feels about as serious as everything else in this film, which is to say, not very. With a director with a name like Savage Steve Holland, what did you expect? Tell the kids this was exactly what growing up in the ‘80s was like. *—D.W.*

Where to watch *Better Off Dead*: Amazon Prime Video (to rent)

The War of the Roses (1989)

Kathleen Turner as Barbara Rose, Danny DeVito as Gavin D’Amato, and Michael Douglas as Oliver Rose in ‘The War of the Roses’.

20th Century Fox Film Corp./Everett

An extra-dark comedy that veers toward sadism, the film is saved by the chemistry and star power of Kathleen Turner and Michael Douglas (fresh off their *Romancing the Stone *series), with an assist from an excellent Danny DeVito. There are no good guys in this divorce, especially when the family estate is involved. Smashing china, falling down the stairs, slugs to the nose, and worse: Even the pets don’t escape the wrath of this toxic couple, and watching them go from happy newlyweds to bitter foes feels, at times, genuinely sad. More than bleak, the film’s been named “one of the nastiest comedies of all time.” *—D.W.*

Where to watch *The* *War of the Roses*: Amazon Prime Video (to rent)

Fear and Loathing in Las Vegas (1998)

Johnny Depp as Raoul Duke in ‘Fear and Loathing in Las Vegas’.

Universal/Everett

This film must be seen to be believed — and for fans of dark comedy, it must be seen. Wickedly hilarious (and just so…*wrong*) from the get-go, this drug-singed, candy-colored nightmare remains a singularly chaotic vision, a freakish holy trinity/chemical reaction between the minds of Hunter S. Thompson, Johnny Depp, and director-ringleader Terry Gilliam.

The story begins with Depp’s voiceover reading Thompson’s famous words: “We were somewhere around Barstow on the edge of the desert when the drugs began to take hold.” As perfect as Depp’s maniacal performance is, he actually serves as the straight man (if you can believe that) next to the half-feral turn Benicio Del Toro conjures up as Thompson’s lawyer, stealing the show every time he blinks. *—D.W.*

Where to watch *Fear and Loathing in Las Vegas*: Amazon Prime Video (to rent)

Four Lions (2010)

Riz Ahmed as Omar in ‘Four Lions’.

Midget Entertainment/Everett

A laugh fest about a bunch of suicide bombers? Yes, we think *Four Lions* might be the textbook definition of “dark comedy.” English filmmaker Chris Morris invites us to laugh at terror, literally, putting the stupidity of these hilariously clueless jihadists front and center. As EW’s critic put it, “These guys are not charming; they’re horrifying in their ignorance, and they cause real damage. But there’s a weird relief to be found in the opportunity to laugh ourselves sick at their expense, if only for an instant.” *—D.W.*

Where to watch *Four Lions*: Amazon Prime Video (to rent)

Ingrid Goes West (2017)

Elizabeth Olsen as Taylor Sloane and Aubrey Plaza as Ingrid Thorburn in ‘Ingrid Goes West’. Neon

The sun-drenched black comedy *Ingrid Goes West* is filled with enough avocado toast, big hats, and selfies to double as an Instagram time capsule. Playing the charmingly unhinged Ingrid, an internet stalker of the highest order, Aubrey Plaza doesn’t hit a false note. And neither does her costar, Elizabeth Olsen, playing a breezy L.A. girl personified. Olsen fully inhabits her role as a popular social media influencer and the object of Ingrid’s obsession. EW’s critic praised the film’s “keen sense for the loneliness and inanity of a life lived online,” calling it a “clever, corrosive little trick of a movie.” *—D.W.*

Where to watch *Ingrid Goes West*: Netflix

Delicatessen (1991)

Jean-Claude Dreyfus as Clapet, Jacques Mathou as Roger, Rufus as Robert Kube, and Karin Viard as Mademoiselle Plusse in ‘Delicatessen’.

Miramax/Everett

Bathed in yellow smoke, this quirky French dystopia is a visually stunning collaboration between Jean-Pierre Jeunet and Marc Caro. If you’ve seen their other work of genius, *The City of Lost Children *(1995),* *you already know what you’re in for: a living, breathing, beautifully surrealist nightmare. And while *Delicatessen* is, without a doubt, dark (the title is inspired by a butcher who uses his carving skills on, gulp, human meat), it’s leavened by fantastic performances and a sense of zany, off-kilter silliness happening within a meticulously crafted world. *—D.W.*

Where to watch *Delicatessen*: Amazon Prime Video (to rent)

A New Leaf (1971)

Walter Matthau as Henry Graham and Elaine May as Henrietta Lowell in ‘A New Life’.

ullstein bild/ullstein bild via Getty

*A New Leaf *is a showcase for the freakishly talented Elaine May, pulling off a triple threat as the writer, director, *and* star. May plays Henrietta, a very rich, very awkward botanist with zero social skills who is targeted by a gold-digging creep (the excellent grump, Mr. Walter Matthau). His plan to marry this adorable nerd, murder her, and take all the cash does *not* go as planned in the most painful way possible (for the audience, too). Poor, innocent Henrietta falls madly in love with Matthau’s character, the first person to shower her with kindness and care. May’s sense of physical comedy is on full display here (her three-minute “trying to put on a dress” sequence, for example, is legendary). *—D.W.*

Where to watch *A New Leaf*: Kanopy

Drop Dead Gorgeous (1999)

Ellen Barkin as Annette Atkins, Allison Janney as Loretta, and Kirsten Dunst as Amber Atkins in ‘Drop Dead Gorgeous’.

New Line Cinema/Everett

Minnesota nice turns into Midwestern murder in *Drop Dead Gorgeous*, a black comedy mockumentary about a series of attempted assassinations in a small town beauty pageant qualifying competition. Amber Atkins (Kirsten Dunst) is a 17-year-old aspiring journalist who hopes to win the Sarah Rose Cosmetics American Teen Princess Pageant to pay for college. But first, she must survive her hometown pageant, a high ask considering someone is picking off the contestants one by one.

This satire is a dark, funny takedown of small-town values, beauty competitions, and the public’s obsession with young girls. The comedy flopped at the box office, but *Drop Dead Gorgeous *proved ahead of its time — the movie cast Amy Adams in her first film role — and has since been declared a cult classic. —*Ilana Gordon*

Where to watch *Drop Dead Gorgeous*: Tubi

Fargo (1996)

Frances McDormand as Marge Gunderson in ‘Fargo’.

Gramercy Pictures/Getty

The OG middle America noir is brought to you by the Coen brothers, whose understated style is often imitated but never duplicated. (Now, if we could include Noah Hawley’s sublime small-screen spinoff we would, because the film and the FX series both mix humor and violence to create a deliciously dark comedy hot dish.) *Fargo* was hugely influential, being one of the first times mainstream moviegoers had seen plain-spoken folk at the center of a violent crime story, and the sensation of laughing while covering your eyes in horror (one word: woodchipper) became a core memory for ‘90s film lovers.

With *super great *performances from the likes of Frances McDormand, William H. Macy, and Steve Buscemi, EW’s critic described the setting as “a landscape so muffled by snow and Scandinavian-bred, low-affect courtesy.” *—D.W.*

Where to watch *Fargo*: Netflix

The Producers (1967)

Gene Wilder as Leo Bloom and Zero Mostel as Max Bialystock in ‘The Producers’.

John Springer Collection/CORBIS/Corbis via Getty

For this, his first film, dark comedy hall of famer Mel Brooks went *big*, deciding that fearlessly taking on the Nazis (and the American public) would be a good introduction. This bold move paid off, cementing his place in cinematic history (and our hearts) forever, but at the time, well, you could say it took some (Space)balls*.* Yes, Brooks created something so risky — people just didn’t *make fun of Hitler* like that — that the studio nearly pulled it from circulation. A pitch from Peter Sellers, interestingly enough, is what saved it. Brooks later admitted his M.O. was this: When it comes to real-life horror, sometimes the only logical response is comedy. *—D.W.*

Where to watch *The Producers*: Tubi

* The Death of Stalin* (2017)

Jason Isaacs as Field Marshal Zhukov in ‘The Death of Stalin’. Entertainment One UK

From Armando Iannucci (*Veep*)* *comes a different sort of barbed political satire, a historical comedy as black as burnt toast. Set in 1953 after the titular dictator’s passing, the film revels in the chaotic, messy, bumbling power struggle that ensues among figures like Nikita Khrushchev (Steve Buscemi) and Georgy Malenkov (Jeffrey Tambor). If this sounds a bit like *Succession* (created by Iannucci’s peer/former co-writer Jesse Armstrong, who worked on *The Thick of It* and *In The Loop* with him), we can only say that great minds think alike. Fun fact: In what may be the greatest compliment of all, the film was condemned by Russia as anti-Russian propaganda. *—D.W.*

Where to watch *The Death of Stalin*: Amazon Prime Video (to rent)

American Psycho (2000)

Christian Bale as Patrick Bateman in ‘American Psycho’.

Lionsgate/Courtesy Everett Collection

Bret Easton Ellis’ 1991 best-seller looks unrecognizable in Mary Harron’s cinematic adaptation of the controversial novel. Starring Christian Bale as Patrick Bateman, a yuppie investment banker whose only real passions are consumerism, dining out, and committing murder, this black comedy and horror fusion satirizes the mass-consumption and performative lifestyle that was a hallmark of the 1980s culture and economy.

Luckily for viewers, the film version of *American Psycho* presents the best aspects of the novel without luxuriating in book Bateman’s fevered misogyny. EW’s critic writes that the film is elevated by Bale’s interpretation, noting, “He keeps Patrick lurching blindly toward humanity, until we see a self being born in a man who, paradoxically, was too selfish to have one.” *—I.G.*

Where to watch *American Psycho*: The Roku Channel

The Lobster (2015)

Jessica Barden as Nosebleed Woman and Colin Farrell as David in ‘The Lobster’. Despina Spyrou

Yorgos Lanthimos, quite possibly* the* reigning dark comedy master of the current era, is never content to stay in the lines. Seemingly on a quest to make a film in each genre, though always through the lens of black comedy, *The Lobster *was his stab at dystopian, absurdist…romance? Starring Colin Farrell (looking like a defeated Ned Flanders) and Rachel Weisz, the story is set in a “resort” (ok, prison) whose “guests” are all singles tasked with finding life partners. If they fail, they are transformed into an animal (hence the title). But hey, it’s not *all *bad — you get to choose the animal! With a stacked cast (Olivia Colman, John C. Reilly, Léa Seydoux, Ben Whishaw) and a cool (cold?) style, this film is an uncomfortable, surreal, and contentious love-it-or-hate-it kind of ride. *—D.W.*

Where to watch *The Lobster*: HBO Max

Sorry to Bother You (2018)

LaKeith Stanfield as Cassius Green and Tessa Thompson as Detroit in ‘Sorry to Bother You’. Annapurna Pictures

EW’s critic praised Boots Riley’s genre-defying dark comedy as “the most wonderfully bizarre film of 2018,” and with good reason. Following telemarketer Cassius Green (LaKeith Stanfield in a role he was born to play) down a *serious* rabbit hole, this twisted, Oakland-based take on *Alice in Wonderland* starts weird and gets progressively weirder, building to a surreal conclusion you cannot look away from. Not to be outdone, the amazing Tessa Thompson turns in a fantastically free-wheeling performance as Cass’ artist girlfriend, Detroit. *—D.W.*

Where to watch *Sorry to Bother You*: Fandango (to rent)

Groundhog Day (1993)

Bill Murray as Phil Connors and Andie MacDowell as Rita Hanson in ‘Groundhog Day’.

Columbia Pictures/Getty

*Groundhog Day* is an existential miracle disguised as a Bill Murray comedy. What appears to be a bouncy, silly romp about a slightly surreal situation (Murray plays Phil, a weatherman reliving the same day over and over) is, at its core, actually quite deep. With director/co-writer Harold Ramis at the helm, this film asks surprisingly big philosophical questions — How do we get unstuck? What mistakes do we keep repeating? What *is* the point of life? — without ever hitting us over the head with them. *—D.W.*

Where to watch *Groundhog Day*: Amazon Prime Video (to rent)

Election (1999)

Matthew Broderick as Jim McCallister and Reese Witherspoon as Tracy Flick in ‘Election’.

If Elle Woods had an evil little sister, she would be Tracy Flick, a frighteningly ambitious girl who blows up a man’s life. Reese Witherspoon (then 23, playing a convincing 16)* owns *the role of Flick, a high-intensity creep with perfect posture, chipper enough to cut. The terror in her teacher’s eyes (Matthew Broderick, bringing the schlub factor) tells us everything — she’s a monster in a sweater set. This one takes place in the heartland (Nebraska), where, similar to *Fargo*, the flat colors and plain-spoken style serve to put the fiery story into high focus. Written and directed by Alexander Payne with his usual self-assured, sunny, satirical edge, *Election* is based on the novel of the same name by an author who is no stranger to the dark (comedy) side, Mr. Tom Perotta. *—D.W.*

Where to watch *Election*: Paramount+

The 20 best A24 horror movies ranked, from 'Talk to Me' to 'Midsommar'

16 hilarious mockumentaries that capture the absurdities of everyday life

Borat Subsequent Moviefilm (2020)

Sacha Baron Cohen as Borat in ‘Borat Subsequent Moviefilm’. Amazon Studios

Sacha Baron Cohen’s mustachioed, overly-confident Kazakh is back, baby, in yet another tragicomic wonder. Traveling through the U.S. with his daughter, Tutar (Maria Bakalova), *Borat Subsequent Moviefilm* is like a reimagined, unscripted version of a bizarro buddy comedy, full of moments *so *unwieldy they give new meaning to the word “awkward.” Some of the most iconic bits include the now-infamous Rudy Giuliani encounter and the horrifying father-daughter OB-GYN visit. As EW’s critic writes, “His outrageous, uncountable isms — the confident screeds against women and Jews, the casual endorsements of incest or indentured servitude — are of course satirical, and entirely the point.” *—D.W.*

Where to watch *Borat Subsequent Moviefilm*: Amazon Prime Video

Being John Malkovich (1999)

(Center): Orson Bean as Dr. Lester and Cameron Diaz as Lotte Schwartz in ‘Being John Malkovich’.

Universal Studios

Pair the dark comedy dream team of Charlie Kaufman (writer) and Spike Jonze (director) with a stellar cast willing to go there (Catherine Keener, Cameron Diaz, John Cusack), and the result is one of the most surreal films ever. *Being John Malkovich* — a wild gem EW’s critic describes as a “delightfully absurdist, occasionally off-putting masterpiece of existential voyeurism that runs on its own off-brand logic,” is a mind-blowing treat. Trying to explain its appeal on paper is almost impossible, but we’ll try. One of the plot devices is a portal/tunnel allowing access to the Malkovich brain. Another is a “half-floor” jammed between two normal, full-sized floors. Also, puppets, obsessive love, body-swapping, a rescue chimp, and more puppets. It’s dream-like and claustrophobic in the best way. *—D.W.*

Where to watch *Being John Malkovich*: Amazon Prime Video (to rent)

In Bruges (2008)

Brendan Gleeson as Ken and Colin Farrell as Ray in ‘In Bruges’. Everett Collection

Dark as a cup of Yorkshire Tea, *In Bruges*, penned by writer/director Martin McDonagh (2022’s *The Banshees of Inisherin*) tells the tale of two hit men visiting the Belgian tourist town of Bruges. The decidedly *not* touristy reason for their visit? One of them, (Colin Farrell) has accidentally killed a young boy, and the other (Brendan Gleeson) has been ordered to off him. The setting for this settling of scores is the film’s third star. Lovely and rich in history, Bruges is famous for its canals, stone bridges, and quaint pubs, painting a charming backdrop for a couple of excellent performances in a film that is quite heavy, but also shockingly funny. *—D.W.*

Where to watch *In Bruges*: Amazon Prime Video (to rent)

Beetlejuice (1988)

Michael Keaton as Betelgeuse, Geena Davis as Barbara Maitland, and Alec Baldwin as Adam Maitland in ‘Beetlejuice’. Warner Brothers/Everett

With its signature sweet but creepy tone, this Tim Burton film is exhibit A in how scary things (death, the paranormal) can be adorable — and the trick is in the perspective. When the world’s nicest couple (Geena Davis and Alec Baldwin) perish and become ghosts, only a certain depressed goth princess named Lydia (Winona Ryder, who else) can see them. Serving as their real-world representative, Lydia defends them against idiots like her parents (nearly “killing” them with a seance) and sleazebag monsters (Michael Keaton‘s slapstick Beetle-dude). Hilariously funny and at times downright scary, this genre-defying movie is creative both in concept (death is kinda like the DMV?) and in aesthetic (a feast of practical effects, namely a stripped sandworm). There simply isn’t a dull moment. *—D.W.*

Where to watch *Beetlejuice*: Amazon Prime Video (to rent)

In The Loop (2009)

Mimi Kennedy as Karen Clark and James Gandolfini as Lt. Gen. George Miller in ‘In the Loop’.

Nicola Dove/IFC Films/Everett

Two words: Armando Iannucci. As fans of *Veep* already know, the man has a serious way with political comedy… the darker, the better. An offshoot of his excellent BBC TV series *The Thick of It*, *In the Loop *is like a nastier version of *The* *West Wing* after 100 pots of coffee. The film, featuring Steve Coogan and James Gandolfini, winningly depicts a bumbling U.S. government running headlong into a Middle East war. As EW’s critic lamented, “*In the Loop* invites its audience to *think*, and presumes a certain love of *Monty Python*. Not to mention an appreciation of *Dr. Strangelove.*” (See No. 1 on our list.) *—D.W.*

Where to watch *In the Loop*: AMC+

After Hours (1985)

Griffin Dunne as Paul Hackett and Rosanna Arquette as Marcy Franklin in ‘After Hours’.

What would happen if Martin Scorsese directed a neo-noir screwball comedy about a corporate yuppie’s ill-fated night in New York City? You’d get *After Hours*, an underrated ‘80s movie featuring some of the decade’s brightest talents. Griffin Dunne stars as Paul Hackett, a hapless word processor who attempts to woo a woman he meets in a coffee shop, only to spend the rest of the film paying for it.

Part of a subgenre of Reagan-era films known as the “yuppie nightmare cycle” — similar movies include *Desperately Seeking Susan *(1985)*, Blue Velvet *(1986)*, *and* Fatal Attraction *(1987) — *After Hours *isn’t as well known as *The King of Comedy *(1982), but it should be. In *After Hours*, Scorsese takes the same frantic approach he uses with his crime thrillers to create a fast-moving black comedy. —*I.G.*

Where to watch *After Hours*: Amazon Prime Video (to rent)

The Royal Tenenbaums (2001)

(From left to right): Luke Wilson as Richie Tenenbaum, Gwyneth Paltrow as Margot Tenenbaum, Gene Hackman as Royal Tenenbaum, Grant Rosenmeyer as Ari Tenenbaum (holding Buckley), Ben Stiller as Chas Tenenbaum, Jonah Meyerson as Uzi Tenenbaum, Anjelica Huston as Etheline Tenenbaum, Danny Glover as Henry Sherman, and Kumar Pallana as Pagoda in ‘The Royal Tenenbaums’. James Hamilton/Disney

*The Royal Tenenbaums* feels vintage in the best way, like something unearthed from our collective consciousness. With its beautifully obsessive, antiqued look — from the color palette to the precision-centered cinematography — its blink-and-you’ll-miss-it doll house details aren’t just there to look pretty. Under the exquisite surface is something quite moving, a grieving family grappling with the kinds of big, swirling, complicated feelings that make life hard and art great. Perhaps EW’s critic said it best: “[T]he Tenenbaum children are precocious and extraordinary, yet not protected from unhappiness by their own gifts.” *—D.W.*

Where to watch *The Royal Tenenbaums*: Amazon Prime Video (to rent)

Some Like It Hot (1959)

Tony Curtis as Joe and Marilyn Monroe as Sugar in ‘Some Like It Hot’. Richard C. Miller/Donaldson Collection/Getty

This whiz-bang, cross-dressingly chaotic flick is as fresh now as it was in 1959 — but hey, writer-director Billy Wilder (1950’s *Sunset Boulevard*) wasn’t called a genius for nothing. Two musicians (dynamic duo Jack Lemmon and Tony Curtis) go full drag while on the run from the Mob (seeing their distinct takes on “feminine” is just one of the joys here) and hop on a train full of traveling female musicians (an all-woman band complete with Marilyn Monroe playing the band’s singer and ukulele player).

No wallflowers here; the women are brash, brassy, and refreshingly bold. And while the on-screen action is champagne for the senses, irrepressibly bubbly and bright, its themes are on the serious side, dabbling in desperation, reinvention, and forgiveness. Everyone in this film has got a con (or five), lying and cheating non-stop, but Wilder doesn’t pass judgment. *—D.W.*

Where to watch *Some Like It Hot*: Tubi

Pink Flamingos (1972)

Danny Mills as Crackers and Divine as Divine in ‘Pink Flamingos’. Everett Collection

Predating trash culture, reality TV competitions, true crime obsessions, and even *Jackass* (see: Divine’s dog poop snack), John Waters’ masterpiece of filth is something you have to see to believe (unfortunately, finding it can be a bit of a challenge). Perhaps EW’s critic said it best, in honor of the 25th anniversary, declaring it hilarious, shocking, and scary: “The film has lost none of its danger, its wit, its psychotic exuberance… *Pink Flamingos* still stands as the purest, most joyful jolt of outrage in movie history.” *—D.W.*

*Pink Flamingos* is currently not available to stream.

Network (1976)

Peter Finch as Howard Beale in ‘Network’.

*Network* is the story of veteran news anchor Howard Beale’s (Peter Finch) on-air mental breakdown, a decline that is exploited by executives at the Union Broadcasting System. Screenwriter Paddy Chayefsky uses *Network *to express the outrage Americans felt over issues like Watergate and the Vietnam War; to paraphrase the film, people were mad as hell, and they weren’t going to take it anymore.

*Network* has been rightfully criticized for its portrayal of Arabs, but the film’s other themes — the rise of reality TV, the media’s exploitation of celebrities, the prioritization of ratings above all else — now seem like prophecies. The acting is also great: EW ranked Peter Finch’s performance as Howard Beale number 11 on our list of the 30 most memorable Best Actor-winning performances.*—I.G.*

Where to watch* Network*: Amazon Prime Video (to rent)

Harold and Maude (1971)

Bud Cort as Harold and Ruth Gordon as Maude in ‘Harold and Maude’.

FilmPublicityArchive/United Archives via Getty

An outsider romance peppered with gallows humor and bubbling over with giddy optimism, *Harold and Maude* is a life-affirming, weirdly wonderful film about a rich kid with a death wish and his love affair with an exuberant 79-year-old woman. Fans of Wes Anderson will appreciate this for vibes alone, from the sweet Cat Stevens soundtrack to the autumn in New York color palette. A big bomb upon release (perhaps not surprisingly, given the love scene and the numerous over-the-top suicide enactments), it’s now considered a beloved cult classic — and the ideal expression of director Hal Ashby’s shaggy, unconventional, open-hearted storytelling. *—D.W.*

Where to watch *Harold and Maude*: YouTube

Ruthless People (1986)

Judge Reinhold as Ken Kesller, Bette Midler as Barbara Stone, and Helen Slater as Sandy Kessler in ‘Ruthless People’.

Buena Vista/Everett

On the lighter end of the dark comedy spectrum,* Ruthless People* is an utter joy from beginning to end, a mid-80s classic that still sparkles today. Silly? Super, but with a pure heart, and real…you know, *feelings* at its core. Danny DeVito plays a scheming, no-good husband whose treatment of his brassy wife (a divine Bette Midler) has you rooting for the kidnappers (soft-spoken rays of sunshine, Judge Reinhold and Helen Slater) who snatch her for ransom. Midler’s creative, extremely DIY basement “gym” (and her resulting mental and physical glow up!) remains one of the funniest, most unexpectedly heartwarming character transformations of that era. *—D.W.*

Where to watch *Ruthless People*: Amazon Prime Video

Adaptation (2002)

Nicolas Cage as Charlie Kaufman and Nicolas Cage as Donald Kaufman in ‘Adaptation’. Columbia Pictures

If you’re looking for a movie that requires all of your undivided, phone-down attention, let us introduce you to *Adaptation.* Nicolas Cage is perfectly cast as a tortured, frumpy, socially awkward screenwriter (is there any other kind?) AND said screenwriter’s twin brother, whose ham-handed, more commercial attempts at writing pays off infuriatingly well. And that’s the whole thing…oh, wait. Did you forget this is a Kaufman joint? Yes, there is a SECOND film nested within the first, starring a little-known actress (Meryl Streep) playing a real-life writer (Susan Orleans) and reenacting her famed, flower-hunting non-fiction tale (*The Orchid Thief*). *—D.W.*

Where to watch *Adaptation*: Amazon Prime Video (to rent)

What We Do in the Shadows (2014)

Jemaine Clement as Vladislav in ‘What We Do in the Shadows’.

The Orchard/Madman Entertainment

The mix of deadpan New Zealand humor and horror is a winning combo in this mockumentary about a vampire clan that later spawned an equally electric FX show of the same name. Birthed from the wryly funny, slightly twisted minds of Jemaine Clement and Taika Waititi, *What We Do in the Shadows *takes a fresh approach to its ancient subject matter, applying a blasé, almost bland, *Real World*-meets-*Guffman* approach to the inherently dramatic vamp lifestyle. Flashes of shocking violence (after all, a guy’s gotta eat) present tonal shifts that work brilliantly, while an inherent sweetness (that ending!) keeps things relatable for us soft-hearted humans. *—D.W.*

Where to watch *What We Do in the Shadows*: Apple TV (to rent)

Heathers (1988)

Winona Ryder as Veronica Sawyer, Kim Walker as Heather Chandler, Lisanne Falk as Heather McNamara, and Shannon Doherty as Heather Duke in ‘Heathers’.

New World Pictures/Everett

No one did edgy teen comedy, ‘80s style, better than the Winona Ryder–Christian Slater dream team. And no one ever will again, because *Heathers* is a (wonderfully) problematic time capsule. Is Slater’s Jason Dean just a gaslighter in James Dean’s clothing? Yes. Are we surprised that a teen suicide satire didn’t age well? Nope. But that’s what a good dark comedy can do: Make you squirm as you laugh. The dialogue is whip-smart, crackling, and basically unprintable here, so you’ll just have to check it out for yourself. (And if the use of red lighting, fire, and smoke doesn’t convince you this is a comedy leaning hard into horror, the murders will.) *—D.W.*

Where to watch *Heathers*: Amazon Prime Video

Withnail and I (1987)

Richard E. Grant as Withnail and Paul McGann as Marwood in ‘Withnail and I’.

Cineplex-Odeon Pictures/Everett

This charmingly shaggy, extremely British, incredibly boozy tale, based on writer-director Bruce Robinson’s own experiences, follows the exploits of two unemployed actors (an iconic Richard E. Grant and his patient beyond measure roomie/enabler, Paul McGann) who’ve “gone on holiday by mistake.” The movie gifts us with the most memorably messed-up train wreck in all creation: Grant’s Withnail, an indelible, sallow-faced cocktail of pity, pomposity, and gin. A celebration of horrible flats, youthful cluelessness, and wide-eyed (if not idiotic) innocence, the film captures a brief snapshot in the timeline of these men’s lives. Like the best dark comedies, its emotional gut-punch (in this case, near the end) isn’t sentimental but happens organically, catching you by surprise. *—D.W.*

Where to watch *Withnail and I*: HBO Max

Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964)

Peter Sellers as Dr. Strangelove in ‘Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb’.

As the film that (many would argue) both defined and perfected dark comedy as a form, placing *Dr. Strangelove* at the top of our list was a no-brainer. Comments from Stanley Kubrick revealing his inspiration for the film — the threat of nuclear destruction was just too wild to present as anything *but* a comedy — could also serve as a thesis statement for the entire genre. Overflowing with powerhouse performances from Sterling Hayden, George C. Scott, and, of course, Peter Sellers (in no less than three roles: President Muffley, Capt. Lionel Mandrake, and Dr. Strangelove himself), the movie’s humor works because it isn’t apparent to those who inhabit it.

“People trying to be funny are never as funny as people trying to be serious and failing. The laughs have to seem forced on unwilling characters by the logic of events. A man wearing a funny hat is not funny. But a man who doesn’t know he’s wearing a funny hat…ah, now you’ve got something,” Roger Ebert wrote in his 1999 review of the film. “The characters in *Dr. Strangelove* do not know their hats are funny.” *—D.W.*

Where to watch *Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb*: Amazon Prime Video (to rent)

***Get your daily dose of entertainment news, celebrity updates, and what to watch with our ******EW Dispatch newsletter******.*****

- Movie Reviews & Recommendations

Original Article on Source

Source: “EW Movie”