10 Of The Greatest Indie Comedies Of All Time Source:

The rise of the indie comedy is a well-documented phenomenon in Hollywood. In recent years, there’s been an explosion of films that seek to capitalize on this new genre, one that attempts to mix quirky, off-beat humor with outsider (or loner) characters, with the requisite romantic drama and usually a choice song or two. While we couldn’t find any concrete definitions of the indie genre, it’s the type of thing where you know it when you see it. With that in mind, we’ve wrangled up 10 of the best and well-known indie comedies we could think of, and we’ll do our best to explain why we love them and why we feel they fit into this oddly mainstream genre that’s given us some of the best films to come out in recent years.

10. Charlie Bartlett

Charlie Bartlett is a classic example of the indie comedy, and for that reason we’ve chosen it to take the number 10 spot on this list. A classic coming of age tale that sees a troubled, wealthy young man (Anton Yelchin) acting as therapist and psychiatrist for the students at his new public school, Charlie Bartlett was neither critically adored nor commercially successful; however, the film has gained an intimate fan base that are quick to praise the movie’s heart and sincerity, along with decent performances from Yelchin, indie darling Kat Dennings, and an immediately pre-Iron Man Robert Downey Jr. Well worth checking out, Charlie Bartlett is one of the few indie comedies on this list you may not’ve seen already. Source:

9. Obvious Child

Jenny Slate is one of the funniest women in Hollywood at the moment, but it’s not just her comedy chops that have the world abuzz. In her latest endeavor, Obvious Child, which sees the comedian playing a comedian (so meta) who, following a one night stand, decides to have an abortion, Slate is given the opportunity to flex her dramatic chops ever so slightly. The result is a funny, poignant indie comedy that that earns a spot on this list not just for being hilarious, but also for being heartfelt and sincere to the point of pain. Obvious Child, which has flown under the radar so far but is destined for the cult status that many of the other indie comedies on this list have already achieved, is a necessary watch for fans of the genre looking to take in something they may not have seen before, and to catch a glimpse of the rising star that is Slate before she makes it big. Source: YouTube

8. Safety Not Guaranteed

This little gem of a film came out of nowhere when it premiered at the Sundance Film Festival in 2012, and has since gone on to become one of the better examples of a successful indie comedy. Safety Not Guaranteed, which was directed by Colin Trevorrow (who used the success of this film as a stepping stone and went on to direct one of the highest grossing films of all time in this summer’s Jurassic World) and stars the uber talented Mark Duplass and Parks and Recreation alum Aubrey Plaza (who was most likely designed in a laboratory somewhere as the ultimate “indie comedy” female lead) as two star-crossed individuals who end up forging a real connection despite some unreal circumstances; the characters meet after Plaza’s female protagonist responds to an advertisement in the newspaper asking for someone willing to travel back in time to rescue an old acquaintance. It’s a fun plot that’s never fully explored, and instead takes a back seat to the developing relationship between the two leads. Source:

7. Wristcutters: A Love Story

One of the defining characteristics of these indie comedies is that they often venture into darker thematic territory than one might be used to seeing in studio produced films. For example, Wristcutters: A Love Story takes place in an intermediary realm between life and death reserved for those individuals foolish enough to commit suicide (the premise is a real bummer, but the movie itself is surprisingly hopeful). A bizarre movie that features two mismatched individuals (played by Patrick Fugit and Shannyn Sossamon) on a trip to discover a recently deceased ex-girlfriend of Fugit’s character, Wristcutters: A Love Story features a diverse cast that also includes Will Arnett, Leslie Bibb, John Hawkes and Tom Waits, an eclectic group that fit well into the movie’s tone and structure. Source:

6. Moonrise Kingdom

We probably could’ve labelled this the “Wes Anderson” list, filled it with his filmography, and called it a day. After all, Hollywood’s most famous auteur director has made a bevy of films that fall under the indie comedy genre, and his distinct comedic and aesthetic style has influenced many of the films on this list. We chose Moonrise Kingdom, one of Anderson’s more recent creative endeavors, to represent him here over the likes of movies like Rushmore and The Royal Tenenbaums simply because Moonrise Kingdom fits so perfectly into the indie comedy genre. It’s a film about a pair of pre-teen lovers (played to excellence by Jared Gilman and Kara Hayward) who escape from summer camp, only to be pursued by their counselors and loved ones (a remarkable group of actors that includes Bill Murray, Bruce Willis, Edward Norton, Tilda Swinton and Frances McDormand). Source:

5. The Boat That Rocked

Some of our readers may have been exposed to this nifty little movie under its alternate title, Pirate Radio (an absolutely moronic switch meant to appeal to American audiences…apparently, they weren’t intelligent enough to catch the “rocked” pun in the original title); however, we first saw it under the name The Boat That Rocked, a swell indie comedy with an astoundingly talented cast that includes the late Philip Seymour Hoffman, Rhys Ifans, Nick Frost, Bill Nighy and Kenneth Branaugh, to name a few. The Boat That Rocked, which tells the story of a radio ship dedicated to broadcasting rock and roll tunes late at night, far offshore and outside of Britain’s harsh content control laws, is a lovable film that features the requisite coming-of-age storyline that is at the center of so many of these comedies. It also happens to feature a rocking soundtrack that includes The Kinks, The Rolling Stones, The Who, The Beach Boys and Jimi Hendrix (we’d expect nothing less from a film about pirate DJs). Source:

4. Lars And the Real Girl

Now, we’ve stated that romantic drama is intrinsic to the genre and form of these indie comedies; however, we never said that the romantic drama had to occur between two people of opposite genders, or even two people at all. In Lars And the Real Girl, the female protagonist takes the shape of a woman, but she very clearly isn’t one; rather, she’s a “RealDoll,” an anatomically correct sexual partner replacement who the movie’s lead character, played by Ryan Gosling, develops romantic feelings for. It’s a strange premise for a film, but one that’s carried out in a surprisingly delicate and sweet manner. For all the strange, perverse inclinations the film could have followed through on, it instead chooses to focus on the inherent sadness of a troubled man like Lars (Gosling) using a doll as a supplement for a real relationship, and then goes on to explore whether there’s even anything wrong with this at all. Source:

3. Juno

Juno is kind of like the indie comedy for indie comedies. In fact, it’s so damn nuanced and perfect at being exactly what you think it’s going to be (that being an indie comedy, with all the requisite parts identified so far) that you kind of forget you’re watching a film at all, and not the deepest utterances of a genre calling out for legitimacy. Juno, which tells the story of the titular character (played by Ellen Page) who becomes pregnant as a teenager and decides to give the baby away for adoption, was an indie darling that exploded onto the mainstream circuit when it debuted back in 2007. Directed by Jason Reitman and also starring Michael Cera, Jennifer Garner, Jason Bateman, Allison Janney and J.K. Simmons, Juno represents most everything you could want in an indie comedy. Source: YouTube

2. (500) Days of Summer

When (500) Days of Summer premiered at the Sundance Film Festival in 2009, expectations were not high. In fact, many people hadn’t even heard of this indie romantic comedy that immediately warns viewers “it is not a love story, but a story about love.” A brutal examination of a failed relationship that lasts exactly 500 days, the film stars Joseph Gordon-Levitt as Tom Hanson, who falls for the beautiful and enigmatic Summer Finn (Zooey Deschanel), only to be systematically destroyed as their relationship fails to achieve the heights he believes it’s destined for. A film filled with hard truths and true hardships, (500) Days of Summer also features an astoundingly good soundtrack and rock solid performances from the supporting cast, including Chloe Grace Moretz, Geoffrey Arend and Mathew Gray Gubler. Source:

1. Garden State

If we were to pinpoint an epicenter of the contemporary indie comedy (there’s always been shades of this genre present in cinema history, but only recently has it come together into a definitive and imitable form), it’d be with Zach Braff’s Garden State, the indie darling that stole hearts and minds when it premiered at the Sundance Film Festival in 2004. Written and directed by Braff, the film follows a young, out of work actor who returns to his home state of New Jersey following the death of his mother. While there, he meets a young woman (Natalie Portman) who helps him find purpose moving forward. A film which has inspired a genre, Garden State went on to win a Grammy Award for Best Compilation Album (its soundtrack is revered among cinema fans). Source:
Jim Halden

Jim Halden

Josh Elyea has been writing about movies and TV for Goliath since 2015.