7 Best Indie Comedy Movies to Watch

Before he developed his signature dollhouse visual style, Wes Anderson made his feature debut with this lowkey, heartwarming, and decidedly not-symmetrically-perfect comedy about a bunch of misfits. Bottle Rocket isn’t as much of an outlier in its director’s storied filmography as might initially seem, however. Written in partnership with college buddy Owen Wilson — who, along with brothers Luke and Andrew, made his acting debut here — the film is delightfully offbeat and unexpectedly moving in the way we’ve come to expect from Anderson. 

Dignan (Owen Wilson) and Anthony (Luke Wilson) are two drifting, boyish twenty-somethings, although only Anthony seems aware of his directionlessness, as Dignan has graciously developed a 50-year life plan for the two of them (complete with hilariously vague bullet-points such as “Make wise investments” and “Own multiple accommodations”). The means to these ambitious ends is a life of crime — specifically, pulling off grand heists. But Dignan’s meticulousness hasn’t accounted for distractions, and his madcap scheme falls at the first hurdle when Anthony falls in love with a housekeeper at the motel they hide out in (Lumi Cavazos). Their sweet romance is one of the film’s many delights, as is its barrelling deadpan humor, which never betrays the warmth of the Wilson brothers’ heartwarming depiction of ride-or-die friendship.

Genre: Comedy, Crime, Drama

Actor: Amanda Welles, Andrew Wilson, Antonia Bogdanovich, Brian Tenenbaum, Darryl Cox, Dipak Pallana, James Caan, Jenni Tooley, Jill Parker-Jones, Julio Cedillo, Julio Cesar Cedillo, Kumar Pallana, Luke Wilson, Lumi Cavazos, Melinda Renna, Ned Dowd, Nena Smarz, Owen Wilson, Robert Musgrave, Russell Towery, Stephen Dignan, Tak Kubota

Director: Wes Anderson

Rating: R

It’s always tricky translating literature to screen. In Shortcomings’ case, it struggles to make its Berkeley and New York settings appear more lived-in than just a few postcard-like frames. You could also tell that the conversations it stirs up about things like representation and mixed-race relationships began in the early aughts, when the novel it was adapted from was first released. But those lapses are small and forgivable in the face of a lovely ensemble cast and a whipsmart script. It also takes a special kind of skill to make a character as fiercely unlikeable as Ben (Min) watchable, to hold up a mirror to the audience and make them stay. Thankfully, it's a skill that Tomine and first-time director Randall Park display with such grace. Ben, Alice (Sherry Cola), and Miko (Ally Maki) are flawed and often pathetic, but they’re also honest reflections of who we become when the demands of self-preservation and romantic openness clash. It’s a little unnerving to hear them verbalize what we've always feared about ourselves, but it’s also exhilarating, not to mention comforting, knowing that we're not alone in feeling this way. Shortcomings works because it doesn't confine itself to genre: it's a character study first, and a romantic comedy second.

Genre: Comedy, Drama, Romance

Actor: Adam Enright, Adrian Tomine, Ally Maki, Boran Anh, Daniel Hank, Debby Ryan, George Deihl Jr., Jacob Batalon, Jess Nahikian, Justin H. Min, Melanie J. Newby, Mike Cabellon, Nikhaar Kishnani, Randall Park, Ronny Chieng, Scott Seiss, Sheldon Best, Sherry Cola, Sonoya Mizuno, Stephanie Hsu, Tavi Gevinson, Theo Iyer, Timothy Simons

Director: Randall Park

Rating: R

Equal parts touching and comical, this portrait of a working-class family in a suburb just north of London features twin daughters who couldn’t be more different—the brainy and good-natured Natalie, and her sneering, layabout sister Nicola. Written and directed by Mike Leigh (Another Year, Happy-Go-Lucky) expect the slow, dreamy representation of British society from one of the country's best and most renowned directors.

Genre: Comedy, Drama

Actor: Alison Steadman, Claire Skinner, David Neilson, David Thewlis, Harriet Thorpe, Jane Horrocks, Jim Broadbent, Moya Brady, Paul Trussell, Stephen Rea, Timothy Spall

Director: Mike Leigh

Rating: R

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.

Genre: Comedy, Drama

Actor: Alan Arkin, Andy Garcia, Bettina Bresnan, Carrie Baker Reynolds, Chad Hessler, Chazz Menendez, Curtiss Cook, Damian Achilles, Daniel Maldonado, Dominik Garcia, Dominik Garcia-Lorido, Emily Mortimer, Ezra Miller, Hallie Cooper-Novack, Hope Glendon-Ross, Ivy Jones, Jee Young Han, Julianna Margulies, Louis Mustillo, Louise Stratten, Lynn Collins, Marianne Ebert, Marshall Efron, Matthew Arkin, Mike Burke, Paul Diomede, Paul Marini, Paul Romero, Rick Aiello, Sarah Saltzberg, Sharon Angela, Steven Strait, Vernon Campbell, Yevgeniy Dekhtyar

Director: Raymond De Felitta

Rating: PG-13

A deadpan anthology of three interconnected stories set in a run-down hotel in Memphis, Tennessee. The film's deliberate pacing, minimalist approach, and observational style are present throughout, capturing the essence of each character and their encounters with the city. 

Director Jim Jarmusch's indie film displays its characters' quirks and desires, all underlined with a love letter to Elvis Presley. Each unique segment has some charm, humor, and soundtrack that creates a palpable sense of time and place even if the sum displaces the overall narrative.

Genre: Comedy, Drama

Actor: Calvin Brown, Cinqué Lee, Elizabeth Bracco, Jim Stark, Jodie Markell, Joe Strummer, Masatoshi Nagase, Nicoletta Braschi, Richard Boes, Rick Aviles, Rockets Redglare, Rufus Thomas, Sara Driver, Screamin' Jay Hawkins, Steve Buscemi, Sy Richardson, Tom Noonan, Tom Waits, Vondie Curtis-Hall, Youki Kudoh

Director: Jim Jarmusch