My Top 5 (That’s Secretly A Top 10) Comedies of the 21st Century

For those of you not familiar with Filmspotting, it’s one of my favorite movie discussion podcasts. Hosts Josh Larsen and Adam Kempenaar are insightful and clever critics and I always feel as though I’m learning something new when I listen, no matter how familiar I am with the films they’re discussing.

Their last episode featured a response to the lack of “pure comedies,” or films made with the most express purpose of getting laughs, on the BBC’s Top 100 Films of the 21st Century. That’s right, we’re back here again. They gave their own top 5s and I was thinking to myself that “I love comedy. I love giving my opinion. I love making lists. Why don’t I make one?”

So, a quick primer on the rules. I’m following their rules mostly. No comedies by filmmakers already on the list, so sorry to Wes Anderson, the Coen Brothers, Richard Linklater, and Pixar. I also wanted to avoid films that are funny, but not necessarily comedy. Sorry to Frances Ha, In Bruges, and Kung Fu Hustle. I’m looking for films that elicited the biggest amount of laughs and that feel the most memorable. Four of those were very clear. The fifth slot, less so. So, rather than force myself to make a decision, I’m following my own damn rules and presenting the five films that vied for the 5th slot. Without further adieu, the number 5s are (in alphabetical order):

5) Five-Way Tie

Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)


Bold and dangerous, Borat feels like the kind of movie that moves closer to sickening relevance when we need to reevaluate things. An uncomfortable and deeply hilarious look at American culture 10 years ago, and all those things still right now.

Hot Fuzz (2007)


Any one of Edgar Wright’s films could have been here. Hot Fuzz, a wickedly clever and visually phenomenal send-up of action cop films and 70s British urban horror, is simply the one I’ve always had the most fondness for, given that it was my first.

Mean Girls (2004)


The most quotable movie of my generation, and the film that announced Tina Fey as a genius and became a career height for almost everyone involved. Specific and insightful while never losing the weird touches that made Fey’s time as head writer on SNL so memorable.

Team America: World Police (2004)


The kind of film that shouldn’t work, yet does in spades. These patriotic puppets, infused with Parker and Stone’s unique satirical perspective, become instantly memorable as a send-up of Hollywood politics as much as Bush-era foreign policy. Plus, a harbinger of The Book of Mormon hilarity to come with some of the best comedy original songs of the era.

What We Do In the Shadows (2015)


Probably one of my most rewatched comedies. Waititi creates a small little world of lovable weirdos and makes it feel surprisingly real. Totally hilarious and a seriously great place to spend some time.

And now, the list that I didn’t cop out on.

4) MacGruber (2010)


This is definitely a film that did not get the respect it deserved at the time, but a second life as a cult classic is turning things around. Based on a series of sketches by Will Forte, MacGruber is the kind of comedy that you can’t believe is happening at every step. Singularly bizarre and buoyed on the riotous performance of Will Forte, this early work from director Jorma Taccone, increasingly making his case as our next great comic director, is the kind of film that needs to be given a second watch if you haven’t already, because you’ll likely want to give it a third or a sixth.


3) Wet Hot American Summer (2001)


As much a historical document at this point as a brilliant comedy, Wet Hot American Summer, essentially a film by the sketch troupe The State, is the beginning of amazing careers for so many of its cast, including Paul Rudd, Elizabeth Banks, and Bradley Cooper. Capturing a weirdly specific group of people with as much truth as it does alt-comedy ironic distance, it’s just a great time with some very funny people.


2) Walk Hard: The Dewey Cox Story (2007)


A parody so good and so scorching it may have actually ended a genre of film, Walk Hard‘s send-up of the 20th century music biopic is pitch-perfect and leaves you unable to watch any of the films it parodies with a straight face ever again. Featuring a turn from comic genius John C. Reilly at its heart, Walk Hard is the kind of film that’s rewarding on its own, and a treasure trove for anyone mildly familiar with what it’s parodying. I catch a new joke or detail every time.


1) Anchorman: The Legend of Ron Burgundy (2004)


This is the movie that made me a comedy nerd. I saw it probably a little too young, but just at the right time. Absolutely 100% joke dense, featuring wall-to-wall brilliant comedic performances, and gags that still make me cry with laughter every time I see them. Adam McKay made a rare comedic masterpiece, the kind that doesn’t have to reveal itself more and more every time, because the original material is just so deeply deeply hilarious. I love this movie.


Don’t make me choose. But probably this:

or this: