Of all the cinematic genres, comedy is the hardest to truly master. Humor is so context-dependent, and changes so wildly from person to person (let alone between generations) that many comedies struggle to have a strong, immediate impact, and a lot of the ones that do soon become outdated and glaringly of their time. However, there have been plenty of comedy movies throughout cinematic history that have proven themselves to be timeless and stand among the best movies of all time.

In a sprawling range that spans from masterpieces of the silent era to striking satires and 70s spoofs, and even to some instant classics of the modern age, comedy cinema is littered with hilarious hits. United by runaway creativity and a universal embracing of the sheer, unbridled joy of a good laugh, these quintessential comedy classics are sure to leave audiences in stitches.

50 'Austin Powers: International Man of Mystery' (1997)

Directed by Jay Roach

Offering emphatic proof that spoof movies didn’t completely die in the 80s, Austin Powers: International Man of Mystery was the perfect parody of what was, at the time, a dwindling Bond franchise. It follows the titular spy, an agent from the 1960s awoken from cryogenic sleep to face off against his arch nemesis, Dr. Evil (also played by Mike Myers), when he returns to Earth and holds the planet to ransom.

The spy spoof is relentless in its pursuit of gags, taking direct aim at 007’s more anachronistic and chauvinistic tendencies with reckless abandon. The end result is so ridiculous that it works, hinging on its parody prowess and its central goofiness to stand among the most brilliantly ingenious dumb comedies ever made. The catchphrases alone are enough to leave fans in hysterics.

49 'Arsenic and Old Lace' (1944)

Directed by Frank Capra

A delightful pivot to the macabre from Frank Capra, Arsenic and Old Lace is a black comedy gem that has maintained its hilarious punch over the decades. It focuses on Mortimer Brewster (Cary Grant), a notorious marriage detractor who is amazed to find himself in love and eager to marry. When he travels home to tell his family the news, he is disturbed by a corpse hidden in the window seat, a discovery that forces Mortimer to take more notice of his aunts’ misdeeds.

Grant excels at the film’s particular blend of fast-paced, frenzied storytelling and the dark comic allure that bubbles to the surface as he learns his aunts are serial killers. While its shock factor has dissipated over the years, Arsenic and Old Lace still thrives as a brilliant comedy that does justice to the Joseph Kesselring play it was based on.

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48 'The Mask' (1994)

Directed by Russell Chuck

It is hard to observe modern cinematic comedy without addressing the seismic impact the physically outrageous genius Jim Carrey had on the genre through the 1990s, with his 1994 picture, The Mask, among the most iconic movies of all time. Presenting Carrey with ample opportunity to flaunt his zany hilarity, The Mask sees him star as a meek bank employee whose life is uprooted when he discovers a mask that contains the spirit of the Norse god Loki.

A wild adventure ensues when he succumbs to the mask’s allure, transforming into a confident playboy with a dangerous criminal urge to boot. Wild and exhilarating, the film displays Carrey at his bombastic, cartoonish best while also coasting on an excellent supporting performance from Cameron Diaz to be a true comedy classic and one of the defining movies of the 90s.

47 'In Bruges' (2008)

Directed by Martin McDonagh

Martin McDonagh has risen to great heights with his ability to mesh black comedy with dramatic punch, notably doing so with the Oscar-nominated The Banshees of Inisherin, which also made exceptional use of stars Colin Farrell and Brendan Gleeson. However, the writer-director's funniest movie is still his debut feature, In Bruges, with the anxiety-inducing crime-dramedy following two Irish hitmen as they are sent to the picturesque Belgian city of Bruges after a job goes horribly wrong.

Embedded within the film's dark comedic allure, there is an unpredictable tale of morality and regret which was largely defining of the picture's brilliance. Also running with fabulous, profanity-laden dialogue, occasional strong violence, and an unforgettably erratic yet hilarious villainous performance from Ralph Fiennes, In Bruges is a laugh-a-minute comedy that thrives as a contemplative tale of crime and remorse as well.

46 'The 40-Year-Old Virgin' (2005)

Directed by Judd Apatow

One of the most polarizing yet celebrated comedies of the 2000s that saw Steve Carell become a noteworthy leading man while also ushering in a new generation of Hollywood comedy stars, The 40-Year-Old Virgin is an outrageous gem that has only grown more hilarious (and more excruciatingly painful) with age. It focuses on an awkward though amiable store clerk whose co-workers learn has never had sex. While his colleagues try to help him lose his virginity, he begins to form a romance with a local shop owner.

While it isn’t shy when it comes to shock humor and contains hilariously juvenile moments like the famous waxing scene, the film finds its true quality in the tenderness with which Carell’s Andy is explored. Beneath the vulgarity and smut, The 40-Year-Old Virgin is one of the most surprisingly earnest rom-coms of the 2000s and a true highlight of 21st-century comedy cinema.

45 'The Jerk' (1979)

Directed by Carl Reiner

The movie which saw Steve Martin truly make the leap from a stand-up comic to a leading man in Hollywood comedies, The Jerk was the actor's first starring role in film. Serving primarily as a vehicle for Martin's effervescent and highly energetic brand of goofy comedy to take center stage, The Jerk follows Navin Johnson (Martin), the adopted son of a black family whose sheltered naivety explodes into a journey of self-discovery which takes him to St. Louis.

Embarking on one chaotic misadventure after another, Navin goes from rags to riches and back to rags again all while pursuing the love of cosmetologist, Marie Kimble (Bernadette Peters). Even finding an unlikely diehard fan in Stanley Kubrick, The Jerk displays Martin at his high-octane best and proves that, when it comes to being stupid, there is no greater genius than Steve Martin.

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44 'Galaxy Quest' (1999)

Directed by Dean Parisot

Lovingly referred to as one of the best, albeit unofficial, Star Trek movies ever made, Galaxy Quest is one of the more underrated spoof movies, winning admirers aplenty through the love and affection it shows its source material. Jason Nesmith (Tim Allen) is a washed-up star of the once-popular sci-fi series ‘Galaxy Quest,’ which has attracted a dedicated cult following. As he and his former co-stars get by appearing at conventions, they are approached by an alien race who has mistaken the series to be historical records and enlists the cast to help them fight an intergalactic tyrant.

Capitalizing on its sensational premise, Galaxy Quest dazzles as a fun-fueled sci-comedy that doesn’t skimp on elements of action and adventure either. Buoyed by an exceptional supporting cast that includes Sigourney Weaver, Alan Rickman, Sam Rockwell, and Tony Shalhoub among others, it transcends its comedy framework to simply be a stunning, pure-hearted spectacle of sci-fi adventure.

43 'A Night at the Opera' (1935)

Directed by Sam Wood