Sure, serious movies tend to be the ones that win Oscars, but many of the best movies of all time have been comedies (and a few have been recognized by the Academy and other awards shows, in all fairness). You can go back to the silent era to see this, as Buster Keaton’s The General and Sherlock Jr. are timelessly funny, and then Charlie Chaplin – with the likes of The Kid and City Lights – also made phenomenally great comedies.
The classics are great and all, but it’s also worth shouting out more recent comedies that, in time, will themselves probably qualify as classics. That’s what the following intends to do, highlighting the best comedy (with some films being dramedies, admittedly, and others being comedies that also float between some other genres) of every year. Humor can be subjective, so you’re particularly unlikely to agree with every pick here, but one can only do their best with the topic at hand, so apologies in advance.
25
‘Bamboozled’ (2000)
Though Bamboozled might not be the best Spike Lee movie, it is one of his boldest, and maybe one of his more underrated ones, too. That’s saying quite a bit, considering Lee has never shied away from heavy topics, as a filmmaker, and Bamboozled handles race and its relation to the entertainment industry, being a spin on The Producers (to some extent), with a plot about a producer trying to get fired from his job by pitching a minstrel show to the network he works for.
It becomes popular, somehow, and then things naturally spiral out of control, in ways that are morbidly funny at first, but eventually more serious and despairing. Bamboozled walks a distinctive line tonally, but Spike Lee does make it work much better than you might expect (or fear) it to, and it stands as one of the bravest/riskiest comedies of the century so far, too.
24
‘Shrek’ (2001)
Just like with The Godfather and its sequel, and Toy Story (1995) and Toy Story 2 (1999), it’s hard to find a common consensus regarding whether Shrek or Shrek 2 is the superior film. Maybe it’s easier to say both are equally great, even if that’s a bit cowardly. Shrek obviously came first, and was probably more groundbreaking, but then Shrek 2 was more mature and just as funny, while introducing some characters who are now staples of what’s become a series/franchise.
But to focus on Shrek (2001), this was a pretty wild animated movie to come out when it did, going right up to the line in terms of what was acceptable to put in a kid’s movie while still keeping it kid-friendly/approachable. It’s a classic (animated or otherwise) because it parodies fairytales while itself feeling like a great – and kind of post-modern – fairytale, being the closest thing the 21st century has given us to The Princess Bride so far.
23
‘Punch-Drunk Love’ (2002)
There have been plenty of comedies starring Adam Sandler (some might even say too many), but few quite like Punch-Drunk Love. The only thing that might be comparable is Uncut Gems, which isn’t always described as a comedy, but is darkly funny alongside being very stressful. Punch-Drunk Love is pretty stressful itself, but it focuses a little more on comedy while also being an unconventional romance film.
Punch-Drunk Love is loosely plotted and more about evoking a certain feeling or atmosphere throughout than anything else, but it is quite funny at times, and also unusually charming.
It’s an unusually short and sweet movie by Paul Thomas Anderson’s standards, being about a man with anger issues and a stressful life finding himself, against all odds, in love with a comparably singular individual. It is loosely plotted and more about evoking a certain feeling or atmosphere throughout than anything else, but it is quite funny at times, and also unusually charming, so long as you’re in the mood for something a bit different, rom-com-wise.
22
‘Windy City Heat’ (2003)
Windy City Heat might be the most obscure movie ranked here, and it’s also, admittedly, the kind of thing that’s not going to be for everyone. It feels like it could be a documentary, albeit one about pranking an individual who is, to put it mildly, an unusual character, for about 90 minutes. Or, he’s in on the joke, and it’s meant to look like a feature-length prank, which itself would be clever, since it feels so authentically uncomfortable.
It’s the Nathan for You dilemma, but put another way, it’s biting, unique, and funny either way. It’s also very cruel, and quite crude, from one point of view, though you might feel like the person who’s targeted throughout had it coming. Windy City Heat is like a roller-coaster that’s genuinely not safe, creaking and feeling like it could fall apart any day now, and then you find out it did actually fall apart four or five months after you rode it, but the danger made it more of a blast at the time, because you survived. If you’ve seen the film, maybe that made sense.
21
‘Shaun of the Dead’ (2004)
The film that established Edgar Wright as one of the most exciting young filmmakers of the 2000s, Shaun of the Dead is about growing up when you should already be grown up, relationship woes, and zombies. Its story involves a man trying to get his relationship and overall life back on track, but he does so in the midst of a zombie outbreak, which naturally causes further complications.
It’s pretty great in a Shrek kind of way (hang on, hear it out), since Shaun of the Dead is another parody that itself also works within the genre it’s parodying. You know, it pokes fun at zombie movies while also being a good zombie movie, especially in its surprisingly quite intense final act. The gory and/or more serious moments are always well-balanced with all the humor, and it just moves at such a good pace throughout, making Shaun of the Dead easily one of the most approachable – and entertaining – zombie films ever made.
20
‘Kiss Kiss Bang Bang’ (2005)
While not huge upon release, only just making back its budget (which wasn’t too high, at just $15 million), Kiss Kiss Bang Bang is probably now definable as a cult movie, or will be once it’s old enough to be a cult classic. It’s a bit like calling a movie an ordinary classic; hard to know the minimum amount of time required before the term applies. It’s either there, or will be one day, in this instance.
Kiss Kiss Bang Bang is about a small-time criminal who finds himself wrapped up in the movie world and also a murder investigation at the same time, and things get complicated very fast, but in a fun way. Truth be told, though, if Kiss Kiss Bang Bang didn’t have any real jokes in it, the whole thing would probably function rather well as a neo-noir/crime/mystery movie. It delivers on multiple fronts, and also has near-career-best performances from its leads, Robert Downey Jr. and Val Kilmer.
19
‘Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan’ (2006)
Like Austin Powers and Anchorman before it, Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan is a movie that was arguably too quotable for its own good. The film was incredibly funny and popular for a while, and then people got tired of all the catchphrases, and so maybe Borat was unpopular/irritating for a while, but it’s now come back around and feels funny again.
Or maybe it was always funny, and maybe it’s unfair to criticize a movie for catching on and being “too” funny (the viewers who don’t quite get the message, though, are another story). Borat is also the film that will always define Sacha Baron Cohen’s writing and acting career, for better or worse, but what he managed to do here, with one of the best satirical mockumentaries ever made, is undeniably remarkable.
18
‘Ratatouille’ (2007)
There was always going to be a lot of humor found in a movie like Ratatouille, since it revolves around a rat who fulfills his dreams of becoming a cook by manipulating a young man who can’t cook, hiding under his chef’s hat and pulling his hair to maneuver him around the kitchen. That’s the elevator pitch, or would’ve been, and a chaotic one at that, but thankfully, Ratatouille still got produced, completed, and released.
At the time of writing, it’s the second-oldest Pixar movie to exist without any sort of sequel, prequel, or follow-up/spin-off (A Bug’s Life is the oldest), and it is a pretty much perfect and self-contained film. Ratatouille can count itself among the finest animated movies of all time, and it manages to be funny and quite moving at the same time, all the while proving compelling and entertaining no matter your age.
17
‘Tropic Thunder’ (2008)
Tropic Thunder is fascinating to revisit, close to two decades on from its initial release. It is a bold film that isn’t afraid to touch upon taboo subjects, which can inspire skepticism regarding whether the whole thing holds up, especially if you haven’t seen it since close to its year of release… but honestly, lots of it does hold up, and some of it’s even funnier now than it was in 2008.
At the risk of over-explaining the joke, or getting pretentious and too analytical, Tropic Thunder works – edgy humor and all – because it targets the film industry, the egos of celebrities, and the shallowness of the entertainment world, especially regarding what is and isn’t considered award-worthy. It’s ruthless and self-deprecating, on the part of many people involved, and it’s easily one of the best satirical films made in (relatively) recent memory.
16
‘Black Dynamite’ (2009)
Functioning as a parody of martial arts/exploitation movies, as well as more of a homage to Blaxploitation movies, Black Dynamite is another cult film that doesn’t have a huge fanbase, but the fanbase it has is passionate. The fanbase should be bigger, too, and maybe it could be, since even though summarizing Black Dynamite in terms of what it parodies and homages might make it sound niche, it’s also pretty easy to find most jokes here funny.
It works as a broad action comedy, and then it’s even funnier if you know what it’s referencing, or if you just watch the film for a second (or third) time and pick up on the jokes you might’ve missed. Black Dynamite does throw so many at you, after all, being reminiscent of other non-stop parodies of old (like Airplane! and The Naked Gun), and honestly not being far off from some of those classics comedy-wise.