The 70 Best Indie Comedy Movies

With an ensemble cast featuring a young Natalie Portman and a less murderous Uma Thurman, Ted Demme’s “Beautiful Girls” recreates the worries and woes that thrive in the minds of a tight knit group of working class friends stuck in their own small town Massachusetts world. Warm, quirky and filled with champagne diamonds, both metaphorical and tangible, for anybody who’s ever walked the thirty something walk, it’s a film that’ll make you want to remember all the friends you wish you still had and actually still do.

Summary: it’s a really unusual movie, especially for a star like Robin Williams. It’s almost an indie film actually. Robin Williams plays Lance Clayton, the father of a typical rude teenage boy Kyle Clayton (Daryl Sabara) wherein Sabara’s character meets an unusual demise, and out of embarrassment of the situation the father ghost-writes a suicide note from his son. This white lie leads to another and another and so on until his lies spread further than anticipated. The movie definitely earns points for making the film that was set out to be made. They wanted to make a dark comedy and a dark comedy was what they made. It’s even uncomfortable to watch at times. Between Lance’s love life and Kyle’s non-existent one there’s enough awkwardness that you feel like you can’t wait to get to the next scene just so this one can be over. All in all the actors did a truly fantastic job. Each character seemed well developed by the individual actor to the point where every gesture, line delivery, and awkward silence seemed too natural and organic. Additionally, the writing was exceptional for this movie, as no dialogue was ever wasted. Each and every little detail in each and every shot of each and every scene was very carefully designed to continually push the aesthetics, this film is a big success.

There’s a certain magic in childhood that makes you see the world with bright eyes– every small task is an exciting quest, not weighed down by budgeting, lack of control, and worry. Riddle of Fire captures that magic on 16 mm film, transforming buying a blueberry pie into a whimsical, chaotic adventure involving covens, witches, and huntsmen in modern day forms, echoing a fairytale with vintage 20th century trappings. It’s certainly nostalgic, but it’s created through stylistic choices instead of constant references on older media franchises. While it does lose some momentum in certain moments, Riddle of Fire is such a charming feature debut.

In this ensemble cast directed by Wes Anderson, we see a very dysfunctional family with three very unique siblings who grow apart from each other due to their father, a charismatic and ever-absent grifter. However, when he announces his immanent death, the whole family is forced to confront each other, themselves and their childhoods as they gather in their patriarchal home together for the first time in years. An absolutely gorgeously filmed movie, the usage of color, pattern and 60’s rock music alone makes it worth seeing, and the beautiful story just sweetens the deal.

Not enough movies tell the stories of the down-on-luck, kind of uncool wolf-pack that still goes out into town with their wallets on chains hanging from their pockets and try their luck with the ladies. Mike, heart-broken actor-comedian pines over his ex long after she’s been gone, while his guys – Trent, Rob and Sue – try to help him get back in the game in a series of nights club-hopping and wingman-ing. You find yourself empathizing with Mike almost immediately if you’ve ever had a broken heart and root for him throughout his highs and fairly embarrassing lows. Sprinkled with clever references and subtle, refreshing humor, Mike’s journey to find closure is more than likely to warm your heart.

As a bonus, the flawed yet endearing gang of twenty-something struggling actors will take you to that charming 90’s nightlife in Los Angeles (with music to die for, by the way) and remind you that boys will be boys and that they’re just doing their best helping each other and themselves to keep it together with lots of “You’re so money, and you don’t even know it!”.

City Island is a lighthearted comedy/drama about the Rizzo family, residents of the titular fishing community in The Bronx, New York. Andy Garcia plays the patriarch of the family who works as a corrections officer, and who decides one day to bring home a young ex-con named Tony under somewhat mysterious circumstances. Tony soon becomes entwined in the dysfunctional household as he develops varying relationships with each family member, even as each of them lives their own secret life apart from the rest. This secrecy drives much of the plot, as their personal mysteries play out in an unexpected and often amusing ways. It’s a lively slice-of-life full of boisterous characters, comedic misunderstandings and ultimately a warm embrace of family unity.

Renton (McGregor), a Scottish twenty-something junkie, must choose to clean up and get out, or continue following the allure of the drugs and the influence of friends. Find out if he chooses life in this brutal yet entertaining Danny Boyle masterpiece. While definitely not for the faint of heart, Trainspotting still manages to be funny at times, and provides an overall very entertaining experience.

Not a lot of people will like Stress Positions, a COVID-era film filled with characters whose ballooning egos make isolation all the more claustrophobic. Critics have used the word “unlikeable” and “obnoxious” to describe them, these mostly queer New Yorkers who populate the decrepit apartments where the film is set in, but if you have room for them, they’ll deliver some of the sharpest criticism of liberal and leftist hypocrisies in a while. The self-awareness of their jokes might get lost at times, but it’s there, and it can be enlightening if you let it in. Together, Terry (John Early) and his friends parse things like race and identity—specifically misogyny and transphobia among gay males, and the rampant exoticism of white people over dark-skinned immigrants. The latter is a subject explored poignantly and delicately through Terry’s nephew Bahlul (Qaher Harhash), a young model from Morocco who seems to be the only one smart enough to identify the follies of the people surrounding him. At its best, the film is a darkly funny exploration of even darker themes, as well as an impressively non-cringe throwback to the early days of the COVID lockdown. But it can also be quite difficult to watch, especially if you’ve had enough of New York solipsistic fare.

Weird: The Al Yankovic Story is a parody of a parody, a multilayered confection of silliness that befits the musician it celebrates. It’s the origin story of Weird Al Yankovic (Daniel Radcliffe) but with the surreal and satirical levels cranked up to a hundred. It’s easy to get lost then, in the movie’s freewheeling giddiness, but Radcliffe has a way of grounding the ultra-heightened comedy with his conviction and charm. The movie also doubles as a who’s who in the 1980s music and comedy scene, and the unlikely pairings it brings together keep you entertained and nostalgic for a simpler, weirder time.

While morbidly titled, there’s an unexpected playfulness to Sometimes I Think About Dying that makes a fairly mundane office relationship into a charming romance. Writer-director Rachel Lambert and lead Daisy Ridley capture Fran’s introversion in inventive ways, with score and image to make her daydreams of death more surreal than morbid, with quiet wistfulness of someone that hasn’t quite figured out how to create casual connection. Some viewers might not jive with the way the film focuses more on visual ideas rather than plot, but Sometimes I Think About Dying sweetly depicts social awkwardness and the alluring curiosity a crush can sometimes create.