Subscribe to Prime Video? In the mood for a rib-tickler? Critic Katie Parker has scoured the platform and retrieved the funniest films—from recent hits to decades-old classics.
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The 40 Year Old Virgin (2005)
Watch on Prime VideoCrass, adolescent and brimming with heart, Judd Apatow’s 2005 directorial debut is among his most likable films. The story of one man’s (Steve Carrell) bid to lose his v-card late in life, The 40 Year Old Virgin kicked off a new style of sex comedy that would become all but ubiquitous for the next decade—but which few have been able to imbue with more sweetness and charm as Apatow did here.
American Fiction (2023)
Watch on Prime VideoThe dark horse of the 2024 awards season, Cord Jefferson’s wry comedy-drama follows a frustrated African American author (Jeffrey Wright) skewering literary stereotypes expected of black writers—only for his satirical novel to be received both unironically and uproariously by the liberal elite. Sharp, incisive, and making the most of its excellent ensemble cast, American Fiction’s irreverent comedy cuts right to the bone.
American Pie (1999)
Watch on Prime VideoIn an age where cinematic sex scenes are hotly debated, the lewd misadventures of Jason Biggs, Sean William Scott, Chris Klein et al. seem like something of a fever dream—but not so long ago, these horny young men brought the box office to its knees. While this tale of teens attempting to lose their virginities would likely meet a very different reception were it released today, it’s still hard to resist the charms of this quintessential 90s sex comedy.
Back To The Future (1985)
Watch on Prime VideoJust shy of 40 years since its 1985 release, sci-fi classic Back to The Future’s cultural impact—and enduring universal popularity—remains all but unparalleled. Propelled by the combined comic talents of Michael J. Fox and Christopher Lloyd, Robert Zemeckis’s zany time travel caper remains as hilarious, rewatchable and crowd pleasing today as ever.
The Big Lebowski (1998)
Watch on Prime VideoIt would probably be fair to call nearly every entry in the Coen brother’s extensive ouvre a cult favourite—but few films have quite the following devoted to their 1998 comedy The Big Lebowski which has inspired, among other things, an annual convention (Lebowski Fest), a religion (‘Dudeism’), and even the names of two species of African spider (Anelosimus biglebowski and Anelosimus dude). Believe the hype—The Big Lebowski is as funny now as ever.
Bridesmaids (2011)
Watch on Prime VideoConsidered a breakthrough for female-led comedy, Paul Feig’s 2011 film following a disillusioned woman’s (Kristin Wiig) misadventures while preparing to serve as maid of honour in her best friend’s wedding was a critical and commercial hit—and over a decade later, it still holds up. On the surface a crass, gross out comedy befitting producer Judd Apatow’s signature style, Bridesmaids also succeeds as a wry deconstruction of female friendship.
Bottoms (2023)
Watch on Prime VideoLed by two of Hollywood’s hottest up and comers, the buzz around Bottoms has been huge—and entirely justified. Emma Seligman’s follow up to her wickedly funny debut Shiva Baby, Bottoms follows a pair of queer teen outcasts (Rachel Sennott and Ayo Edeberi) who, in the hopes of hooking up with hot cheerleaders, start a women’s fight club at their school. Audacious, outrageous and featuring a montage set to Avril Lavigne’s “Complicated”, Bottoms is irresistible.
Buffalo ’66 (1998)
Watch on Prime VideoFor all his flaws (and there are quite a few), Vincent Gallo’s contributions to cinema are not to be underestimated—and Buffalo ‘66, his 1998 indie comedy is good enough to instantly erase all memory of his edge lord antics. Following an ex-convict (Gallo) who kidnaps a tap dancer (Christina Ricci) and forces her to pretend to be his wife in a plot to impress his parents, this strangely sweet little comedy is a cult classic for a reason.
But I’m a Cheerleader (1999)
Watch on Prime VideoFollowing an all-American teen cheerleader sent to a conversion therapy camp when her straight-laced parents suspect her of being a lesbian, Jamie Babbit’s wry 1999 satire was lightyears ahead of its time. Starring Natasha Lyonne and Clea DuVall alongside New Zealand’s own Melanie Lynskey, But I’m A Cheerleader’s combination of edgy humour and heartfelt romance polarised critics on release—and make it more than worthy of its cult status today.
The Lobster (2015)
Watch on Prime VideoFamously absurdist auteur Yorgos Lanthimos may now be famous for his frequent collaborations with Emma Stone, but not so long ago Colin Farrell was the apple of the Greek directors eye—and together the pair created some of their best work. A masterstroke of black comedy set in a world where single people are turned into animals, this deliciously disturbing and eccentric film is one of modern cinema’s most original satires.
Miss Congeniality (2000)
Watch on Prime VideoIt’s been nearly 25 years since Miss Congeniality cemented Sandra Bullock as one of the most winning rom-com stars of our time—and to this day it’s nearly impossible to resist its charms. The story of a federal agent going undercover as a beauty queen, this endlessly quotable film (the “perfect date” joke will go down in comic history) is a timeless fish-out-of-water crowd-pleaser.
No Hard Feelings (2023)
Watch on Prime VideoMany of us lament the dearth of sex comedies that once dominated the early 2000s box office: a call finally answered by 2023’s No Hard Feelings. Starring Jennifer Lawrence as a struggling slacker hired by a pair of overly anxious parents to deflower their socially awkward 19-year-old son (Andrew Barth Feldman) before he heads off to college. A rude, raunchy romp with all the sweetness of a romcom, No Hard Feelings is the answer to your sex comedy prayers.
O Brother, Where Art Thou? (2000)
Watch on Prime VideoWhen it comes to off-beat comedy, you can’t go wrong with the Coen Brothers—and this satirical comedy, loosely based on ancient Greek epic poet Homer’s Odyssey, is among their best. Following three escaped convicts (George Clooney, John Turturro, and Tim Blake) on the run in rural Mississippi in the 1930s, O Brother, Where Art Thou? joins the trio on a series of misadventures as they try to outrun the law.
Palm Springs (2020)
Watch on Prime VideoThe past few years have seen a boom of time loop movies, but few perfected the genre quite like 2020’s Palm Springs. Following two strangers (Andy Samberg and Cristin Milioti) who hook up at a destination wedding only to get stuck in a seemingly infinite time loop, that has them living the last 24 hours on repeat, forever, this solid, self-assured and incredibly winning romcom is one of the best in recent memory.
The Princess Bride (1987)
Watch on Prime VideoHaven’t seen The Princess Bride? Inconceivable! Widely considered a cult classic and a career best for director Rob Reiner, over 35 years since its release The Princess Bride remains one of the most quotable—and rewatchable—comedies of all time. Starring Cary Elwes, Robin Wright, Mandy Patinkin, and Wallace Shawn, this twist on the traditional fairytale combines action, romance and post-modern comedy to create one of modern cinema’s most beloved tales.
A Simple Favour (2018)
Watch on Prime VideoAppearing on the surface to be yet another melodramatic domestic thriller, Paul Feig’s gleefully silly 2018 black comedy turns the usually somber genre on its head. Following a widowed mummy-blogger (Anna Kendrick) who becomes obsessed with the mysterious disappearance of a glamorous new friend (Blake Lively), the increasingly bonkers twists come thick and fast in this deliciously twisted and delightfully campy flick.
Step Brothers (2008)
Watch on Prime VideoCrude, cringeworthy, and completely, hilariously silly, Adam McKay’s 2008 film is an under-sung piece of modern comedy gold. Starring Will Ferrell and John C. Reilly as two spoiled adult men who, having never flown the nest, find themselves living together when their parents get married, Step Brothers’ brand of no-holds-barred vulgarity is not for everyone, but can’t be overlooked by comedy lovers.
