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Only 5 Comedy Movies in the 2020s Can Be Considered True Masterpieces

Only 5 Comedy Movies in the 2020s Can Be Considered True Masterpieces

Comedy remains one of the most versatile and widely intricate methods of storytelling. The notion of letting audiences laugh alongside a film allows for some genuinely beautiful story beats and emotional weight. At the same time, laughter is an infectious joy that, while seemingly easily replicated, is largely unmatched when a comedy film is firing off at maximum strength. The 2020s have had several exceptional comedies, but in terms of cinematic perfection, only five films have reached the mantle of comedy gold.

From insightful and philosophical films that utilize humor to amplify their deeper themes to wild, uncompromising visions of passion and creativity that are a blast from start to finish, these comedy films are the very best of an already great decade. While the very prospect of a list that ranks and chooses the very best of comedy is difficult, considering how everyone’s tastes fluctuate and are different from one another, these films stand out as some of the most engaging, well-crafted offerings since 2020.

‘The Worst Person in the World’ (2021)

Renate Reinsve as Julie running down the street in The Worst Person in the World.
Image via SF Studios

The romantic comedy has been one of the most tried-and-true subgenres of comedy, dating back to the golden age of cinema. While there are several to choose from, The Worst Person in the World stands out as not only the best-crafted but the most emotionally insightful and strikingly beautiful rom-com of the 2020s, too. This layered Norwegian coming-of-age film chronicles four years in the life of Julie (Renate Reinsve) as she navigates the troubled waters of her love life and struggles to find a concrete career path, forcing her to look inward at the aimless nature of her life.

While many romantic comedies are quick to create lavish, over-the-top and unrealistic worlds and characters that act more as tools for comedy over any impactful storytelling, The Worst Person in the World has its cake and eats it too by having insightful, layered, and realistic characters while not losing a touch of its wit or comedy. It might not be as rambunctious or over-the-top as the other entries on this list, but its distinct style of subtle, layered comedy mixed with insightful storytelling and beautiful filmmaking makes The Worst Person in the World a major accomplishment for rom-coms. It’s so impactful that it is not only among the best comedy movies of the 2020s, but also one of the best romance movies of the past 5 years.

‘The Holdovers’ (2023)

Paul Giamatti and Dominic Sessa as Angus and Paul standing in snow in The Holdovers
Paul Giamatti and Dominic Sessa as Angus and Paul standing in snow in The Holdovers
Image via Focus Features

An entertaining and comedic duo can make all the difference in terms of elevating a film to all-time comedy status, a prospect entirely understood by The Holdovers. The film skyrockets to cinematic heights thanks to its portrayal of the unlikely friendship of a troublemaker student (Dominic Sessa) and a stern instructor (Paul Giamatti). The comedic chemistry between this duo makes for one of the most wildly entertaining, exceptionally heartwarming, and genuinely emotional duos in modern comedy. Each actor brings out the best in one another, with their characters learning and growing as a result of their time together and coming out the other side with a better perspective on the world and their vastly different generations.

However, the primary duo proves to be only a single aspect of the pristine excellence that has transformed The Holdovers into the definitive holiday classic of the 2020s. The Oscar-winning supporting performance by Da’Vine Joy Randolph brings additional layers of emotion and depth to the story, while the winter setpieces add a distinct comfort and joy. At times, The Holdovers feels like the cinematic equivalent of a joyous holiday party with family, as while it isn’t without its wild hiccups and infighting, it comes out the other end making you feel all warm and happy inside like only the absolute best holiday comedies can achieve.

‘Nirvanna the Band the Show the Movie’ (2026)

Two men walking down the street in Nirvanna-the-Band-the-Show Image via NEON

On the one hand, it may seem absolutely preposterous to include a film that came out in 2026. However, those who have experienced the madness and comedic brilliance of Nirvanna the Band the Show the Movie will be quick to sing its praises and understand exactly why it has confidently earned its spot among the very best. This Canadian love letter and film adaptation of the cult classic comedy web series turned television series is about as effortlessly charming and filled with passion as a modern comedy could hope to achieve. Best friend comedy duo Matt Johnson and Jay McCarroll have been honing their craft and the comedic mileage of these characters for decades now, with this film feeling like a culmination of their craft.

This absurd comedy film follows the duo’s titular wannabe band attempting to get a show at the Rivoli theater, a goal that they have been fighting for and performing elaborate schemes to accomplish since 2008. However, after their latest plan goes awry, the duo unintentionally finds themselves traveling back in time and getting stuck back in 2008, getting into all sorts of mischief and risking changing history as they try to find a way back home. Even to those who are completely unaware of the original web series or Matt Johnson’s previous directorial works, Nirvanna the Band the Show the Movie is an effortlessly entertaining sci-fi comedy that speaks to the distinct style of personality-fueled comedy that defines independent comedy of the 2020s. The overwhelming praise that the film has received is not unwarranted, as it’s already earned its spot among the best comedy films of the 2020s and possibly even the 21st century.

‘Poor Things’ (2023)

Greek director Yorgos Lanthimos has been the absolute king of strange and uncomfortable dark comedies that simultaneously have audiences laugh and recoil in confusion with their mixture of unsettling themes, biting satire, and comedic wit. While many of his films have scratched this distinct itch, Poor Things broke through the mold not only as his most acclaimed and successful film to date, but also became the blueprint for perfect dark comedies of the 2020s. It features a strange, uncomfortable premise that inherently alienates a section of the audience. The approach allows the film to go all out in terms of its strange worldbuilding and sense of comedy, being all the better for it. It blends striking visuals with unrestrained dark comedy and insightful messaging to create one of the funniest comedies of the 2020s.

The film sees Emma Stone as Bella Baxter, a woman brought back to life by an unorthodox scientist who transported the brain of an unborn child into the body of its suicidal mother. Running off with a lawyer to explore the world with the mental acuity of a child and the body of a fully-grown adult, Bella soon learns the grimy truths of the human experience as she comes into her own to stand for equality and liberation. Between all the wild concepts and lunacy present, Emma Stone’s masterful performance as Baxter makes for the perfect balance between the wild and thought-provoking sides of the film. She makes for one of the all-time great comedy protagonists, as effortlessly hilarious as she is strikingly well-written and masterfully performed.

‘Hundreds of Beavers’ (2024)

Jean Kayak, played by Ryland Brickson Cole Tews, holds out a hand in 'Hundreds of Beavers'.
Jean Kayak, played by Ryland Brickson Cole Tews, holds out a hand in Hundreds of Beavers.
Image via Cineverse

The essence of great comedy is that even with a minuscule budget and a fraction of the resources of contemporary blockbuster comedies, a truly great vision and execution can make all the difference in terms of top-notch laughs and charm. No low-budget comedy exemplifies this masterfully woven understanding like Hundreds of Beavers, a wild and unrestrained love letter to slapstick and manic, absurd comedy. It’s one of the safest bets that Hundreds of Beavers will be a massively celebrated classic in 50 years, as its distinct flavor of creativity and passion makes the film one of the most enthralling and entertaining experiences in years.

The film sees a drunken applejack salesman having his livelihood destroyed, forcing him to take up the prospect of fur trading in order to survive the harsh winter. As he grows more effective at learning and taking down the various animal creatures of the North American forest, he ends up creating an unexpected feud with the local group of beavers. From its goofy usage of mascot costumes for all the animals to green screens that make its characters feel like living cartoons, Hundreds of Beavers has a sense of comedic timing and wit that feels like the digital era evolution of classic slapstick movies. It’s a masterful combination of comedy styles, new and old, that is emblematic of everything that makes comedy such a limitless and exceptional genre, as its very existence paints an amazing picture for the future of the genre in the digital era and beyond.

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Deadspin | Oilers star Connor McDavid (ankle) game-time decision for Game 5 <div id=""><section id="0" class=" w-full"><div class="xl:container mx-0 !px-4 py-0 pb-4 !mx-0 !px-0"><img src="https://images.deadspin.com/tr:w-900/28807959.jpg" srcset="https://images.deadspin.com/tr:w-900/28807959.jpg" alt="NHL: Stanley Cup Playoffs-Edmonton Oilers at Anaheim Ducks" class="w-full" fetchpriority="high" loading="eager"/><span class="text-0.8 leading-tight">Apr 24, 2026; Anaheim, California, USA; Edmonton Oilers center Connor McDavid (97) looks on after scoring a a power play goal during the third period against the Anaheim Ducks in game three of the first round of the 2026 Stanley Cup Playoffs at Honda Center. Mandatory Credit: Kiyoshi Mio-Imagn Images<!-- --> <!-- --> </span></div></section><section id="section-1"> <p>As the Edmonton Oilers face possible elimination from the playoffs Tuesday night, they may have to do so without star center Connor McDavid, a game-time decision due to an ankle injury.</p> </section><section id="section-2"> <p>McDavid sustained the injury to his right ankle in Game 2 and continued to play but has appeared limited.</p> </section><section id="section-3"> <p>The 29-year-old captain has one goal and three assists in the series after leading the league with 138 points (48 goals, 90 assists) in 82 games during the regular season.</p> </section><br/><section id="section-4"> <p>The two-time defending Western Conference champion Oilers are down 3-1 in the best-of-seven first-round series against the Anaheim Ducks, who visit Edmonton on Tuesday night for Game 5 looking for their first series win in nine years.</p> </section> <section id="section-5"> <p>Anaheim has won three in a row after blowing a late lead and dropping the series opener 4-3 on April 20.</p> </section><section id="section-6"> <p>The Oilers may also be without fellow center Jason Dickinson, who missed Games 2 and 3 with a lower-body injury before returning for Game 4. Dickinson is also a game-time decision.</p> </section><section id="section-7"> <p>–Field Level Media</p> </section></div> #Deadspin #Oilers #star #Connor #McDavid #ankle #gametime #decision #Game

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