10. O BROTHER, WHERE ART THOU? (2000)
Attempting an cinematic adaptation of Homer’s The Odyssey is pretty daring to begin with, but placing it in 1930s’ Mississippi is another thing entirely. Somehow also managing to also be a tribute to Preston Sturges’ Sullivan’s Travels, the Coen brothers’ follow-up to Fargo and The Big Lebowski was one of their most complex films to date. Its constantly changing tone and subgenre keeps the movie from ever being predictable, making you feel smart at the references you get and stupid at the ones that go over your head. (Bonus points for being the movie to truly cement George Clooney as more than just a rom-com lead, after dabbling in above-average parts in Out of Sight and Three Kings. The following year’s Ocean’s Eleven would launch him into the next echelon of stardom and other comedic roles would follow — see #4 — but all can be traced back to his Golden Globe Award-winning turn in O Brother, Where Art Thou?.)
9. IN THE LOOP (2009)
Technically, In the Loop is a spin-off of the British TV series The Thick of It. But one need not know The Hobbit to appreciate The Lord of the Rings. Four years before becoming the twelfth lead of Doctor Who, Peter Capaldi was Malcolm Tucker in the political comedy In the Loop, satirizing the loony backroom antics of the British and American governments. Every decade, a movie redefines what it means to be the most (verbally) vulgar comedic masterpiece, and South Park: Bigger, Longer & Uncut had a good run, but In the Loop set the new standard, inventing new bon mots of apoplectic obscenity nearly every minute. Writer-director Armando Iannucci knows his political comedy, too; a few years after In the Loop, he created Veep for HBO.
8. WET HOT AMERICAN SUMMER (2001)
Long before the Netflix sequel series brought it back like an Adult Swim cartoon, the subversive movie Wet Hot American Summer was a cult comedy with a massive following, due in no small part to the fact that A) it starred a litany of before-they-were-famous faces like Amy Poehler, Bradley Cooper, Joe Lo Truglio, Paul Rudd, Christopher Meloni, and Elizabeth Banks; B) it sprung off the improv-based comedy of MTV sketch troupe The State, to define where our post-modern/meta comedic sensibilities would eventually go, years before Hollywood and audiences would catch up to it; C) it flat-out changed comedy. That last point is hard to overstate as, even in the top 10 of this list, only a five or six movies can truly claim to have redefined the genre. The fact Wet Hot American Summer doesn’t seem very ground-breaking today is a testament to how prescient and revolutionary it truly was in 2000.
7. SHREK (2001)
Movies labelled “animated comedies” are rarely actually comedies, so much as they’re usually comedically-inclined animated family movies. Shrek is an absolutely pure comedy, from heart to sleeve. A buddy comedy that’s animated more due to cinematic necessity than narrative excuse — it would probably just be a live-action/CGI blend today — Shrek is the perfect example of not reinventing the wheel but of manufacturing a perfect wheel (with just enough of a design twist to make it seem new). Ogre Shrek (Mike Myers) finds himself on a quest for the Lord Farquaad (John Lithgow) in exchange for his swamp, “aided” by a talking donkey (Eddie Murphy). A cast of sharp comedians, a clever script, and a subversive lesson or two ultimately combine into one of the greatest comedies of the last couple of decades, animated or not. Just ignore the sequels.
6. LOVE ACTUALLY (2003)
The Blair Witch Project of modern comedies, Love Actually is more blamed for the all the Valentine’s Days, He’s Just Not That Into Yous, New Years’ Eves, Mothers’ Days, and The Family Stones it begat than credited for how much it changed things. Richard Curtis had already found success writing movies like Four Weddings and a Funeral and Bridget Jones’s Diary, but for his directorial debut, he took inspiration from the intertwining tales spun in years past by Robert Altman and applied the formula to ten stories about love that intersect, criss-cross, and upend expectations by not even all ending happily. Afforded a massively talented cast partially by the virtue of each actor only needing to carry a little of the cinematic weight, Love Actually is the pinnacle of the modern romantic comedy.
5. NAPOLEON DYNAMITE (2004)
Many of the greatest comedic characters of film were ruined by people endlessly quoting and impersonating them — see: Ace Ventura, Austin Powers, and Jack Sparrow, to name a few — but the best ones become funny all over again once re-approached with the benefit of time. Napoleon Dynamite was an anomalous comedy when it hit the indie scene in the summer of 2004, with many not really “getting” it or understanding how it was even supposed to be funny. For those on the same wavelength as the debut from Jared and Jerusha Hess, though, it was a bracing new breed of comedy that dared to laugh at its pathetic lead character instead of pitying or sympathizing and encouraging the audience to do the same. Jon Heder’s breakthrough performance was so different and peculiar, many people still forget it was just acting. Flippin’ sweet, indeed.
4. FANTASTIC MR. FOX (2009)
Wes Anderson was already a master of exploring the tragicomedy and comedic tragedy of the family dynamic, in everything from Rushmore and The Royal Tenenbaums, to The Life Aquatic with Steve Zissou and The Darjeeling Limited, when he released his greatest masterpiece: a stop-motion adaptation of a Roald Dahl children’s story about foxes. As lunatic as the premise may sound, Fantastic Mr. Fox ended up the greatest animated movie of the last two decades. Anderson’s shots have always felt posed, his characters really just dolls for him to tell his stories with; here, he gets the absolute control of every aspect of the image that he always wanted. George Clooney, Meryl Streep, and Jason Schwartzman are brilliant as the Fox clan, aided by a very impressive supporting cast. The simple caper of Dahl’s becomes an examination of middle-age malaise and the cost of reliving glory days even greater than The Incredibles. 2018’s Isle of Dogs has its work cut out for it.
3. KISS KISS, BANG BANG (2005)
Screenwriter Shane Black is one of the greatest unsung heroes of movie comedy-dom, creating the modern buddy/action-comedy template still used today, with his debut script Lethal Weapon. After losing the faith of Hollywood by the mid-’90s, Black returned a decade later with a new script, the desire to direct, and a pair of actors who’d also lost the faith of Hollywood. Robert Downey, Jr. — in the role that would get him cast as Tony Stark one year later — stars as a burglar who stumbles into an audition during a getaway and gets cast as a private-eye in a movie. For prep, he’s sent to LA to shadow an actual detective (Val Kilmer), but almost immediately, the two find themselves embroiled in a real murder plot and a conspiracy they can barely stay ahead of. Downey, Jr. and Kilmer are a blistering funny odd couple and Black’s banter between the two of them his greatest work. So much of the last decade of movies can all be traced back to Kiss Kiss, Bang Bang, and still none of its successors have surpassed it.
2. BORAT: CULTURAL LEARNINGS OF
AMERICA FOR MAKE BENEFIT
GLORIOUS NATION OF KAZAKHSTAN (2006)
Remember a few entries ago, when I talked about Napoleon Dynamite being ruined by drunks and your “funny” boss doing their impressions until the humour was lost? After two years, those same people traded in “Lucky” and “Sweet” and “Very nice” and “Great success.” Borat was ultimately dulled in the same fashion, but even its endless quoting couldn’t detract from how revolutionary Borat was for new comedy. On the heels of the neo-mockumentary movement’s The Office and Arrested Development, comedian Sasha Baron Cohen spun one of his three characters from the improvised reality sketch series Da Ali G Show, clueless Kazakh journalist Borat Sagdiyev, into a fake travelogue through America too funny to be scripted. Baron Cohen deserved Oscar recognition for his brilliant comedic skills here, especially with how astoundingly he stays in character as the unaware Americans around him expose their own racism and ignorance. The fact Borat is almost remembered more now for the endless Halloween costumes it birthed than for its utter magnificence as a comedy is a real tragedy.
1. THE 40-YEAR-OLD VIRGIN (2005)
It could only be The 40-Year-Old Virgin. Not only is it quite simply the strongest comedy to come out since the Y2K scare, but it’s the perfect storm of everything that has come to define how we consume modern comedy, a Venn diagram encircling The State, Christopher Guest, and Judd Apatow. Not to mention being the true birth of the careers of Steve Carell and Seth Rogen; The Office and Knocked Up may have been their breakthrough successes, but The 40-Year-Old Virgin made it all possible. The comedic premise of three goofballs discovering a 40-year-old co-worker of theirs is a virgin — and making it their mission, in each of their misguided ways, to rectify that — could have gone either way, but Apatow walks the perfect line, burying real heart and emotion just below every swear word and “You know how I know you’re gay?” joke and being unafraid to examine unspoken vulnerabilities in the modern male. Every cylinder fires perfectly in The 40-Year-Old Virgin, and its impact on comedy and movies in the 12 years since is immeasurable. Plus, it’s just funny as all hell. For all those reasons and more, it’s the best comedy of the new millennium.