333 Best Quirky Movies to Watch (Page 9)

Staff & contributors

When the mildly weird and funny come together, great things happen—especially in film. Whether you’re up for some alternative comedies or romantic dramedies, here are the best quirky movies and show to stream now.

Remarkably, Steven Soderbergh was only 26 years old when he directed this coolly assured debut, the searingly candid script of which he also wrote in just eight days. Despite the pornographic implications of its title, this is more concerned with exploring whether honesty — not sex — is the means to real intimacy. In fact, the only nakedness glimpsed here is of the emotional kind, as twenty-something drifter Graham’s (James Spader) total aversion to lying has an infectious influence on everyone around him.

The primary recipient of that disarming effect is Ann (Andie MacDowell), the wife of Graham’s old college buddy who is blasé about sex and neurotic about everything else. Talking to Graham has a therapeutic effect on her, but he takes something else away from conversation: chronically impotent, he simulates the sexual experience by conducting erotically themed interviews with women on videotape. Preferring to sublimate his desires through his camcorder, Spader’s physically aloof character is a disturbingly prescient one for what it suggested then about technology’s future impact on human relationships. That Soderbergh managed to conduct such a complex psychosexual drama all through dialogue — on his first feature, no less — makes him exceedingly worthy of the record this earned him of the youngest solo Palme d’Or-winning director ever.

Genre: Drama

Actor: Alexandra Root, Andie MacDowell, David Foil, Earl T. Taylor, James Spader, Laura San Giacomo, Peter Gallagher, Ron Vawter, Steve Brill, Steven Brill

Director: Steven Soderbergh

Rating: R

Strange things are happening in the sleepy cul-de-sac where Cameron Edwin (comic Jim Gaffigan) lives: cars are falling from the sky, space rockets are crash-landing in his backyard, and his doppelgänger has just moved in next door and stolen his job. Unnerved by all these weird occurrences and feeling like a failure in light of his looming divorce, Cameron goes full midlife crisis and decides to rebuild the damaged rocket as a last-ditch attempt to fulfill his lifelong dream of being an astronaut. It’d be giving too much away to say anything more about the plot, but suffice it to say that the uncanniness lurking under Linoleum’s surface comes to mind-bending fruition as the rational and the fantastic meld into one. Though it’s already deeply affecting on first watch, this is the kind of movie you’ll immediately want to rewind to absorb the full weight of.

Genre: Comedy, Drama, Science Fiction

Actor: Amy Hargreaves, Gabriel Rush, Jay Walker, Jim Gaffigan, Katelyn Nacon, Michael Ian Black, Rhea Seehorn, Tony Shalhoub, Twinkle Burke, West Duchovny, Willoughby Pyle

Director: Colin West

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Of the many violence-inflected black comedies that Pulp Fiction spawned, Grosse Pointe Blank ranks among the best. Though it’s patently inspired by Tarantino’s magnum opus — John Cusack plays a sardonic, amoral hitman, and the film features bursts of stylized violence and a retro soundtrack — it never feels derivative. The film finds its own identity as a quirky romcom when Cusack’s character, Martin Blank, returns to his hometown for a 10-year high-school reunion on the advice of his terrified therapist (Alan Arkin).

Martin is experiencing professional disillusionment as part of the quarter-life crisis that often takes hold when one realizes it’s been a whole decade since high school. His profession puts a darkly comic spin on that convention, but the film doesn’t treat that element entirely flippantly. Unlike Martin — and so many of the film’s Pulp Fiction-inspired brethren — Grosse Pointe Blank isn’t nihilistic, but quite sincerely romantic. Its hybrid nature and surprising heart come to the fore in Martin’s renewed relationship with the girlfriend he jilted at prom: Debi (Minnie Driver), now a ska-loving radio DJ. Cusack and Driver have sparkling chemistry, which makes the sincerity with which their characters grapple with the possibility of a second chance at happiness all the more absorbing to watch.

Genre: Action, Comedy, Drama, Romance, Thriller

Actor: Alan Arkin, Ann Cusack, Barbara Harris, Belita Moreno, Benny Urquidez, Bill Cusack, Bobby Bass, Carlos Jacott, Dan Aykroyd, David Barrett, Doug Dearth, Hank Azaria, Jenna Elfman, Jeremy Piven, Joan Cusack, John Cusack, K. Todd Freeman, Michael Cudlitz, Minnie Driver, Mitchell Ryan, Steve Pink

Director: George Armitage

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Frances (Greta Gerwig) lives in New York – but not the glamorous NYC of Woody Allen movies. Taking place primarily in the gritty and rapidly gentrifying North Brooklyn, the black and white film paints a picture of an extended adolescence. Focusing on the goofy and carefree Frances, who loses her boyfriend, her best friend and her dream of being a dancer. She moves in with two guys, both of whom are more successful than her, and becomes even more determined to fulfil her goals, impractical as they may be. Fans of HBO’s Girls and other odes to not being a “real person” yet will love this film.

Genre: Comedy, Drama

Actor: Adam Driver, Britta Phillips, Charlotte d'Amboise, Christine Gerwig, Cindy Katz, Daiva Deupree, Dean Wareham, Eleanor Smith, Finnerty Steeves, Gibson Frazier, Gordon Gerwig, Grace Gummer, Greta Gerwig, Hannah Dunne, Isabelle McNally, Josh Hamilton, Juliet Rylance, Justine Lupe, Laura Parker, Lindsay Burdge, Marina Squerciati, Maya Kazan, Michael Esper, Michael Zegen, Michelle Hurst, Mickey Sumner, Noah Baumbach, Patrick Heusinger, Peter Scanavino, Ryann Shane, Teddy Cañez, Vanessa Ray

Director: Noah Baumbach

Rating: R

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Two misfits, an immigrant and a traveling cook, team up to start an unlikely enterprise in this slow but captivating drama. The story, set in 19th century Pacific Northwest, evolves around the arrival of the first cow to that part of the world. This presents a unique opportunity that the two main characters try to benefit from. 

First Cow is a mix between a Western and a modern-day plot-less indie drama.  It has likable characters, stunning scenery, and a fascinating look into how social outcasts lived back then.

Genre: Drama, History, Western

Actor: Alia Shawkat, Don MacEllis, Dylan Smith, Eric Martin Reid, Ewen Bremner, Gary Farmer, Jean-Luc Boucherot, Jeb Berrier, John Keating, John Magaro, Kevin-Michael Moore, Lily Gladstone, Mary Ann Perreira, Mike Wood, Mitchell Saddleback, Orion Lee, Patrick D. Green, Phelan Davis, Rene Auberjonois, Scott Shepherd, T. Dan Hopkins, Ted Rooney, Toby Jones, Todd A. Robinson

Director: Kelly Reichardt

Rating: PG-13

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After Jackie and Spencer, the dark satire El Conde is a surprise new entry in Pablo Larraín’s stacked filmography. Already, the film has prominent differences– it’s shot in black and white, starting with narration from an unseen and posh Englishwoman that makes the film’s events feel like entries in Bridgerton’s scandalous newsletter. The subject is far from the beloved wives of presidents and princes– it’s centered around a notorious Chilean dictator who remains unpunished for his crimes. However, as his fictional vampire version deals with his rightfully ruined legacy, El Conde proves to be a witty satiric twist to Larraín’s usual themes. Through familial squabbles over ill-gotten wealth, confessions and exorcism conducted by a nun, and certain foreign interventions, El Conde paints an everlasting greed that continues to haunt Larraín’s homeland.

Genre: Comedy, Fantasy, Horror

Actor: Aldo Parodi, Alessandra Guerzoni, Alfredo Castro, Amparo Noguera, Antonia Zegers, Catalina Guerra, Diego Muñoz, Dindi Jane, Eyal Meyer, Francisca Walker, Gloria Münchmeyer, Jaime McManus, Jaime Vadell, Marcelo Alonso, Marcial Tagle, Mateo Iribarren, Patricia Rivadeneira, Paula Luchsinger, Stella Gonet

Director: Pablo Larraín

Rating: R

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You don’t have to have seen a single game of tennis to enjoy this mockumentary about the longest match that (n)ever took place in the sport’s history. Andy Samberg plays Aaron Williams, the mullet-sporting adopted brother of Serena and Venus (whose family “reverse Blind-Sided” him) made immortal by his record-smashing, week-long battle with posh, dim-witted English prodigy Charles Poole (Kit Harington) at Wimbledon. Things only get more riotously ridiculous from the premise: the team behind sports spoof Tour de Pharmacy chronicle the winding journeys the rivals took to that climactic seven-day showdown, from forays into the world of innovative underwear design to stints in Swedish jails, by way of a surreal tangent into the storied faux-history of courtroom sketch art. Suffice it to say: the tennis isn’t really the point here.

Real-life figures from the sport (including Serena Williams and John McEnroe) ground the spoof in enough reality to make the zany humor pop, with the comedy coming from a very game Fred Armisen, Michael Sheen, Lena Dunham, Will Forte, and Howie Mandel. With eccentric humor in spades — from the puerile to the surreal — and a lean runtime, 7 Days in Hell packs in as many dizzying jokes as Aaron and Charles do volleys in their absurd history-making rally.

Genre: Comedy, TV Movie

Actor: Andy Samberg, Chris Evert, Chris Romano, David Copperfield, Destiny Soria, Dolph Lundgren, Filip Hammar, Fred Armisen, Howie Mandel, Jerry Gregorio, Jim Lampley, John McEnroe, Jon Hamm, June Squibb, Karen Gillan, Kit Harington, Lena Dunham, Ludwig Manukian, Lyssa Roberts, Mary Steenburgen, Michael Sheen, Serena Williams, Soledad O'Brien, Will Forte

Director: Jake Szymanski

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The Murder Case of Hana & Alice is a charming and whimsical anime film that tells the story of two teenage girls who team up to investigate the mysterious disappearance of a classmate. The film is beautifully animated in a rotoscoped style giving it a unique and dreamlike quality. Hana and Alice, who is new to the town, decide to team up to solve the case. 

Part mystery, part coming-of-age story, and part slice-of-life make for a refreshing and unpredictable viewing experience as the film commits itself to each. The cast makes the story funny and heartwarming with their well-timed quips and well-written dialogue. This is a truly unique and enjoyable animated film about a beautiful friendship budding most unexpectedly.

Genre: Animation, Comedy, Drama, Mystery

Actor: Anne Suzuki, Haru Kuroki, Kaku Tomohiro, Midoriko Kimura, Ranran Suzuki, Ryo Katsuji, Sei Hiraizumi, Shoko Aida, Tae Kimura, Tomohiro Kaku, Yu Aoi

Director: Shunji Iwai

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Like a Wes Anderson movie, The Last Black Man in San Francisco takes artistic risks and nails every one of them. There are many quirky, aesthetically well-studied, and even funny aspects to this moving story.

Jimmie has been maintaining a typical San Francisco Victorian house, regularly painting the windows and watering the plants. One small problem: other people live there and they don’t want him around. It turns out this was once Jimmie’s family house, having been built by his grandfather in 1948, and he misses it deeply.

This story is based on writer Jimmie Fails’ life, as he tried to reclaim his family home in SF. However, it’s not a movie that limits itself to gentrification. It transcends that to being about the universal yearning to find a place to call home.

Genre: Drama

Actor: Andy Roy, Daewon Song, Danny Glover, Finn Wittrock, Isiain Lalime, Jamal Trulove, Jello Biafra, Jimmie Fails, John Ozuna, Jonathan Majors, Mari Kearney, Mike Epps, Rob Morgan, Thora Birch, Tichina Arnold, Tonya Glanz

Director: Joe Talbot

Rating: R

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