100 Best Underrated Comedy Movies of All Time

A young bisexual woman attends a shiva, caught between her parents and their expectations, her ex, and her sugar daddy. Rachel Sennott’s Danielle is yet to find her path in life and everyone is determined to remind her of that. Taking place almost entirely in real-time, the film’s sharp wit is contrasted with constant anxiety, complemented by Ariel Marx’s horror-like score, full of discordant pizzicato that sounds like every last bit of sanity snapping.

It’s a sex-positive take on 20-something life, treating bisexuality as wholly unremarkable and passing no judgment on Danielle’s sugar daddy income. Its specificities about Jewish customs and traditions are non-exclusionary, while its social claustrophobia is achingly universal. It’s comforting in the way it portrays the social horrors we all face, the feeling that everyone but you has life figured out, and that – ultimately – those who matter will pull through, eventually. One of 2021’s best.

Of all the Christmas-set films to have come out over the last couple of months that were, inexplicably, about grief and regret (you’d be surprised by how many there are), The Holdovers easily outdoes its contemporaries by being confident enough to just sit with its characters. Like the best of director Alexander Payne’s other films, there are no melodramatic crescendos or overcomplicated metaphors; there are only flawed individuals going about their lives, occasionally noticing the things that bind them together. Payne’s gentle touch means the characters (and the audience) aren’t forced to “solve” their grief, but allowed to come to terms with it in their own way, with each other.

Payne evokes the film’s 1970s setting through a muted color palette and analog—almost tactile—sound design, giving warmth to this New England despite all its snow and chilly interiors. It’s understandable that these characters are similarly cold to each other on the surface at first, but they manage to thaw the ice simply by taking the chance to listen to each other’s pain. It’s the kind of film in which relationships develop so gradually, that you hardly notice until the end how much mutual respect has formed between them when they return from their dark nights of the soul back to their status quo.

The Commitments is the kind of film you show someone you like to test who they are. If they like it, they’re good people. If they don’t, they’re probably soulless. It’s very hard to find fault in The Commitments, a ‘90s Irish musical following a band of aimless young people hoping to escape their troubled realities one rehearsal and gig at a time. They may be penniless and uneducated, but when they take on the stage, these soul (not jazz!) performers will dazzle you to no end. The cast was chosen primarily for their musical chops and it shows—these kids can sing. And when they start, you wish they’d never stop. The lead singer, Deco (a 16-year-old Andrew Strong) is the most arresting out of them, but all 11 of them are very easy to like and follow, even through that difficult but suitable ending.

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.

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.