The 50 Best Indie Comedy Movies

The 50 Best Indie Comedy Movies

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The best highly-rated but little-known comedy movies as featured on agoodmovietowatch.com.

Note: to see if each film is available for you to stream on Netflix or elsewhere, click on the title to be redirected to the movie page.

30. Red Rocket (2021)

7.4

Country

United States of America

Director

Sean Baker

Actors

Bree Elrod, Karren Karagulian, Shih-Ching Tsou, Simon Rex

Moods

Dark, Depressing, Dramatic

When Mikey Saber’s porn career takes a dip in California, he returns to an estranged wife in Texas, where he meets new and old friends alike and attempts to rebuild his life through a couple of odd jobs. Though Mikey eventually earns his keep, his vanity and eagerness to succeed at all costs threaten to get the best of him.

All this happens against a vibrant backdrop of local sights, beautifully lit and framed by director Sean Baker (The Florida Project, Tangerine). Quaint, naturalistic, and ever-so-subtly political, Red Rocket is another great entry into Baker’s impressions of the vexed American Dream.

29. Living in Oblivion (1995)

7.5

Country

United States of America

Director

Tom DiCillo

Actors

Catherine Keener, Danielle von Zerneck, Dermot Mulroney, Hilary Gilford

Moods

Dark, Easy, Funny

A young Steve Buscemi leads this wry farce about a calamitous film set where nothing goes right. The sardonic script skewers the ins and outs of low budget film production and the various personalities on set from belligerent directors, pretentious cinematographers, and egotistic actors. 

A playful three-act structure and trips into dream sequences keep things light, while a strong supporting cast, including a cheeky appearance by Peter Dinklage and the fantastic Catherine Keener, gives the film the backbone it needs. 

28. Secretary (2002)

7.5

Country

United States of America

Director

Steven Shainberg

Actors

Amy Locane, Ezra Buzzington, James Spader, Jeremy Davies

Lee Holloway (Maggie Gyllenhaal) is compassionate and diminutive, but her social awkwardness hinders her as she attempts to navigate young adulthood. After recently being hospitalized for self-harm, Lee is determined to prove she is capable of autonomously taking care of herself. She begins working as a secretary for E. Edward Grey (James Spader), a meticulous attorney.

It’s not long before both Lee and Edward realize they’re attracted to one another’s opposite natures: Lee’s obedience and Edward’s dominance. They begin a mutually consensual BDSM relationship, with both experiencing a sexual and emotional awakening. 

The premise may sound familiar: 50 Shades of Grey is widely acknowledged as, at the very least, owing its title to Secretary. But while 50 Shades of Grey portrays an unhealthy, toxic, and superficial idea of a BDSM affair, Secretary maintains that consent must be at the core of any relationship. And ultimately for Lee and Edward, BDSM becomes a way for them to communicate and overcome their individual pain, and unite stronger as a vulnerable, loving whole.

27. Wonder Boys (2000)

7.7

Country

Germany, Japan, UK

Director

Curtis Hanson

Actors

Alan Tudyk, Bingo O'Malley, Charis Michelsen, Elisabeth Granli

Moods

A-list actors

Michael Douglas plays Grady Tripp, a craggy, lovable English professor struggling to finish the follow-up to a very successful first novel. It has taken him 7 years, and it’s an obvious metaphor for his ridiculous life. The character navigates various tragicomic dilemmas with a stellar supporting cast including Frances McDormand, Tobey Maguire, and Katie Holmes. His editor is Robert Downey Jr. and his nemesis is Rip Torn. Bob Dylan wrote the theme song. How do you not love this movie? It’s one of those films that feels like a warm, cozy house (despite the fact that it takes place in a Pittsburgh winter), and it’s a great blend of humor and drama.

26. Big Night (1996)

7.7

Country

United States of America

Director

Campbell Scott, Stanley Tucci

Actors

Allison Janney, Campbell Scott, Caroline Aaron, Christine Tucci

Moods

Easy, Feel-Good, Romantic

There are comfort food movies, and then there are films like Big Night: comfort food movies about comfort food. Stanley Tucci and Tony Shaloub are brothers running a failing Italian restaurant. Their last chance to save it from foreclosure is to throw a colossal dinner bolstered by a dubious promise of a visit from singer Louis Prima.

The comedy is mellow and pleasant, and Tucci and Shaloub have wonderful chemistry as bickering brothers. Meanwhile, a great supporting cast featuring Isabella Rosellini, Ian Holm, and Allison Janney more than make up for the somewhat predictable script.

 

25. Trollhunter (2010)

7.8

Country

Norway

Director

André Øvredal, André Øvredal

Actors

André Øvredal, Anton Yelchin, Eirik Bech, Glenn Erland Tosterud

Moods

Funny, Weird

Filmed as a “found footage” of a Norwegian college film crew investigating local poachers, this movie really surprised me. To be fair, I didn’t really know what to expect. But I definitely didn’t expect to like this movie as much as I did. The pacing is on point. The suspense hits you at just the right times. There are a few drops of humour trickled throughout to keep a smile on your face. And that’s how my face stayed when the credits rolled.

24. Bathtubs Over Broadway (2018)

7.8

Director

Dava Whisenant, Female director

Actors

Chita Rivera, David Letterman, Florence Henderson, Martin Short

Moods

Easy, Feel-Good, Instructive

Even if you’re a huge Broadway fan, you’ve probably never heard of the “industrial musical.” While it no longer exists in practice, in the 1970s industrial musicals were shows that corporations commissioned for some of the biggest Broadway names to produce. The script would be based on the company’s offerings and history, and privately performed by real Broadway actors to audiences made up exclusively of company and factory staff.

Now, a documentary about industrial shows doesn’t scream “entertaining,” but to describe Bathtubs Over Broadway in such a manner would be selling it way short. It’s really about Steve Young, a comedy writer for David Letterman, and how his life changed when he found his first industrial musical LP when leafing through a crate of old records for a Late Night segment he was working on.

Ultimately, what makes this such an enjoyable watch is the protagonist’s enduring passion over what at first appears to be nothing but a niche obsession. But with time, as he connects with other collectors and the people who were involved in the original industrial musical productions, his passion breeds community and lifelong bonds. Even if you’re no fan of Broadway, this makes for a great pop culture documentary and an unexpectedly touching story of human connection.

23. Say Anything… (1989)

7.8

Country

United States of America

Director

Cameron Crowe

Actors

Amy Brooks, Bebe Neuwirth, Bill Stevenson, Chynna Phillips

Moods

Feel-Good, Heart-warming, Lighthearted

The ’80s saw an influx of coming-of-age dramas, with John Hughes’ “Brat Pack” films reigning supreme. For better or worse, their most iconic scenes are embedded in pop culture, like students dancing in detention in The Breakfast Club or Sixteen Candles’ belated birthday cake. Perhaps the most iconic ’80s movie moment comes not from Hughes, but from Cameron Crowe’s Say Anything…: Lloyd Dobler (John Cusak) in a trenchcoat, blue Malibu parked behind him, boombox raised over his head in defiant loyalty.

On their last day of high school, Lloyd Dobler resolves to ask out the class valedictorian Diane Court (Ione Skye). Their summer-long relationship is awkward, intense, tender—and familiar to anyone who has ever opened themselves up to falling in love. Say Anything… emotionally outclasses its contemporaries, as Crowe’s writing lends itself to two authentic characters fleshed out beyond caricatures. And as Lloyd crushes hard on Diane, it’s hard not to feel like you’re falling in love with each of them, too.

22. The Grand Seduction (2013)

7.9

Country

Canada

Director

Don McKellar

Actors

Brendan Gleeson, Cathy Jones, Gordon Pinsent, Kevin Lewis

Moods

Feel-Good, Funny, Lovely

The Grand Seduction, a remake of 2003 French-Canadian film La Grande Séduction (2003), is a lighthearted comedy about the residents of the small fishing village of Tickle Head, Newfoudland attempting to convince a young doctor to become its long-term caregiver in order to secure a contract for a new petrochemical facility. Desperate to guide the town out of its impoverished conditions and lack of employment opportunities, the citizens band together to pull ever bit out of deceit and chicanery out of their hats (in often laugh-out-loud fashion) in order to sway the young doctor Paul (Taylor Kitsch) into believing that Tickle Head is where he belongs. It’s a lighthearted and funny story, despite undeniably familiar shades of The Shipping News, Doc Hollywood and Funny Farm. Brendan Gleeson is particularly good as the new mayor of town and Paul’s head “seducer”. He gives the film that extra bit of humanity and wry humor that lifts it above the familiar plot points and into “notable recommendation” territory.

21. Palm Springs (2020)

7.9

Country

United States Hong Kong, United States of America

Director

Max Barbakow

Actors

Andy Samberg, Brian Duffy, Camila Mendes, Chris Pang

Moods

Easy, Feel-Good, Funny

Andy Samberg, Cristin Milioti (Modern Love, Black Mirror), and J.K. Simmons star in this easy but original rom-com that takes place in a wedding time loop. Nyles (Samberg) finds himself living the same day over and over again, so he gives in to the monotony and the fact that there is no way to escape it. 

When he is about to hook up with one of the guests, Sarah (Milioti), he is attacked by a mysterious character. The routine of his time-loop is broken. 

Palm Springs is often surreal and philosophical, which are not adjectives usually used to describe rom-coms. It offers just enough twists to be original without jeopardizing the things that make it a good rom-com.

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