100 Best Underrated Comedy Movies of All Time

The worst possible things that could happen, happen to orphaned twins Gracie and Gilbert but still they power on, motivated solely by the hope of being reunited once more. It’s a sweet premise, young siblings on opposite ends of the country encouraging one another with heartfelt letters. And with the soft-spoken Gracie (Snook) narrating the whole thing, it’s easy to be lulled into a sense of ease and comfort. But those familiar with director Adam Elliot’s work know that it’s never that simple. The film is as dark and edgy as it is sentimental and hopeful. It’s a complex piece of work, one that asks: is life worth living? After all the hardships, misfortune, depravity, and brutality, must we go on? You probably know what answer the movie will give you, but how it gets there is a heart-shattering journey that’s worth taking nonetheless.

Will Ferrell plays a well organized IRS agent named Harold Crick who seems to have figured out everything in his life to the dot. Little does he know his life is being run by someone else, a nervous and morbid novelist, famous for ending her works with the death of the main character. As the nature of his life and eventual doom, he decides to lay back and enjoy the ride, breaking all his ingrained and boring habits. While this film is recommended for everyone, Will Ferrel fans, especially, need to watch this to see Will’s acting variety.

Two-time Oscar nominee Don Hertzfeldt crafts this provocative film in the most skillful way. With only stick figure drawings and some stock footage, he compellingly walks you through the crumbling mind of a man. It is funny. It is sad. It is unsettling. Unlike most movies – or perhaps any movie – there is no point in the film where you feel safe. Unpredictable. Engrossing. Disturbing. By the end of it, you will not be sure what you’ve just seen, but you will feel as if it has changed you. **Personal suggestion: do not watch alone late at night**

Hirokazu Koreeda can do no wrong. The director of Shoplifters and Still Walking is a master of dissecting complex family dynamics through a handful of events. In Our Little Sister, three close sisters who live at their grandmother’s house learn that their absent father has passed. They travel to the mountains to attend his funeral and meet their half-sister, Suzu, for the first time. Suzu is invited to live with the sisters and join their bond.

This movie is a true-to-the-form slice of life, it’s almost drama-free. This absence of plot is an absence of distractions: the sisters are all that matters to Koreeda. His only focus is on how this family becomes bigger, sees past grief, and how the group of close-knit sisters that grew up together can make room for a new addition.

With a premise straight out of a cheesy sci-fi B-movie, you wouldn’t expect Little Shop of Horrors to be a bona fide spectacle, and yet its tale of a wish-fulfilling yet bloodthirsty plant remains as thrilling and intense as ever. More importantly, Alan Menken and Howard Ashman’s rock-musical songs remain boisterous and theatrical, gleefully performed by Rick Moranis, Ellen Greene, Steve Martin, and Levi Stubbs. And buried underneath all this is a comedy with a heart of darkness and a legitimately disturbing morality tale.

Musicals and horror movies are genres that typically cater to a more niche audience, but Little Shop of Horrors should be fun enough to draw anybody in, thanks to the film’s impressively tactile sets, director Frank Oz’s knack for physical comedy, and animatronic special effects that look better than most CGI creations today. As both a horror movie monster and a massive puppet, the vicious plant named Audrey II is entirely worth the price of admission, no matter which version of the film you seek out.

While the film adapts some of Shakespeare’s histories, you don’t need to know Shakespeare to appreciate My Own Private Idaho. In fact, instead of focusing on the Prince Hal character, Scott Favor (Keanu Reeves), the film centers on his narcoleptic friend Mike Waters (River Phoenix). Both of them are young street hustlers in Portland. However, unlike Favor, Waters has no reliable family, inheritance, or support system waiting for him to give up his job. Waters only has his body. Writer-director Gus Van Sant doesn’t really focus on the sex or the narcolepsy – these flash by us only as a state-of-mind experience, with time-lapses and freeze-frames to impart to us Waters’ detachment. Instead, Van Sant cares more about Waters’ seeking connection. It’s why the surreal shots speed by us so fast, and why the natural, lived-in scenes remain in our heads. It’s why Waters’ campfire confession, crackling under Phoenix’s earnest voice, feels so powerful. And it’s also why his later rejection feels so painful.

With a premise as insane as this—a high school coming-of-age film adapted from 410 consecutive tweets from a real, random Thai girl under the username @marylony—you would expect Mary Is Happy, Mary Is Happy to be some sort of incoherent commentary about social media. What director Nawapol Thamrongrattanarit gives us instead is a completely original and surprisingly affecting portrait of a young woman in her senior year trying to come to terms with the fact that her life may only ever be a mess of incongruous parts without a definite identity. It’s as whimsical as it is bittersweet, with the film flitting back and forth between the absurd and the melancholic.

Thamrongrattanarit structures his film as a series of loosely connected vignettes, with every single one of @marylony’s tweets appearing on screen. The effect is one-of-a-kind—as if we’re watching different layers of meaning constantly interacting with each other, our understanding of what we’re supposed to think of as serious or tongue-in-cheek always changing. And through the film’s deliberately lo-fi aesthetics, the experience of watching it is like flipping through a scrapbook of memories mundane and precious.

Don’t be fooled by its obvious parallels to Ghost (not a bad film, but a very different one): Truly, Madly, Deeply isn’t much concerned with the supernatural logistics of its back-from-the-dead-boyfriend premise, and it doesn’t feature any psychics or murders, either. In fact, there’s an argument to be made that everything that takes place here happens in its protagonist’s imagination — that’s how much it ignores the ‘how’ of it all.

Instead, this deeply warm rom-com from the great Anthony Minghella grapples head-on with the emotional challenges of grief and moving on. Juliet Stevenson’s performance as the bereft Nina is up there as one of the most moving portrayals of loss the screen has seen, and not just because of how believable her intense cry-acting is. When she realizes her deceased boyfriend Jamie (Alan Rickman, as seductive and sardonic as always) has returned to the land of the living, her euphoria brings to aching life the dream that everyone who’s ever lost a loved one must surely have dreamt: how joyous it would be to see them again. Blending such raw observations with wry humor — and anchored by two leads with genuine chemistry — this is a profoundly moving and rewarding movie.

Like so many pictures about the pictures, The Player is a biting satire of the biz. Tim Robbins plays Griffin Mill, a Hollywood executive who gives dinner speeches about movies being art but works at a studio where endings are unceremoniously tweaked for maximum audience approval ratings — and therefore maximum profits. The greedy corporate Tinseltown of The Player feels very close to the franchise-pumping Tinseltown of today, but there’s enough wit and irony here to keep it from feeling too depressing.

Legendary New Hollywood director Robert Altman packages his critique in familiar clothing: that of a film noir. After receiving threatening postcards from a disgruntled writer he never called back, Griffin takes matters into his own hands and soon finds himself living out the plot of a taut thriller. The Player gets even more deliciously meta than this: nearly every scene contains a winking reference to the movies, and it’d probably be easier to count which stars of past and present don’t show up for a cameo here. What’s more, Altman gives The Player the kind of “happy ending” that Griffin’s studio is always demanding from writers — only here, it’s spun into a bitter commentary on the whole industry. Simply masterful.

Martin Scorsese had just spent a year prepping for The Last Temptation of Christ when Paramount Pictures unceremoniously pulled the plug on the movie just one month before production was due to start. After Hours was Scorsese’s way of exorcising all that disappointment and frustration, and you can feel it: this black comedy vibrates with manic intensity as it charts a night from hell in the life of Paul (Griffin Dunne), a somewhat scuzzy yuppie living in ‘80s New York City.

In keeping with its title — which suggests the movie is suspended in temporal limbo — After Hours feels like it takes place in some mythological hellscape, a demonic underworld in which everyone Paul meets has been sent forth with the express mission to make his life more miserable. Surreal coincidences pile up, deepening his paranoia and turning his simple goal of returning home into a labyrinthine quest for survival on the deserted, rain-soaked streets of SoHo. It’s the kind of celluloid nightmare that terrorizes and thrills you at the same time (a la the Safdie brothers’ best works, which draw inspiration from After Hours). Only a director of Scorsese’s caliber could turn profound professional disappointment into such a win as this.