Don Hertzfeldt's films are funny, visually striking, insightful, emotional, breathtaking, crude, and heart-wrenchingly sad, often all at the same time. He makes biting satirical works, emotional character studies, outlandish sci-fi films, and crude student films, and he excels at every single one. He's arguably the best, most vital filmmaker of the 21st century, and he does it all by himself with little more than some crude stick figure drawings.
11. Ah, l'Amour (1995)
Hertzfeldt's first film is a crude, rude, and undeniably bitter comedy short about a man killed in increasingly absurd ways. The death scenes are admittedly pretty funny, and the animation is absolutely fantastic for an 18-year-old, but Hertzfeldt's first film is almost certainly his worst.
10. Wisdom Teeth (2010)
Wisdom Teeth was a way for Hertzfeldt to escape from the prolonged, draining process of animating It's Such a Beautiful Day, his three-part magnum opus. While that film is a feature-length character study, Wisdom Teeth is a shocking and gory callback to Hertzfeldt's earliest student films. It's charmingly weird and gory, but it's immature and simple compared to the It's Such a Beautiful Day trilogy. That was absolutely Hertzfeldt's intent, but my point still stands.
9. Lily and Jim (1997)
Dialogue has never been one of Hertzfeldt's strong suits, but that's normally on purpose, most of his films work better when the dialogue is filled with non sequitur, or when there's no dialogue at all. Romantic stories usually need dialogue, however, and as such Lily and Jim has the best dialogue of any of his films, mostly improvised by actors Robert May and Karin Anger. The film drags, and it's occasionally unbearably cringe-worthy to watch, but it was Hertzfeldt's first film to move away from crude slapstick and really explore the human condition, all through the lens of an awkward and doomed relationship.
8. The Simpsons - "Clown in the Dumps" Couch Gag (2014)
In the past couple of years, The Simpsons has had many guest animators come in and bring their unique voices to the series' tried-and-true couch gags. Banksy, Guillermo del Toro, Bill Plympton, and Sylvain Chomet have all done wonderful jobs, but Don Hertzfeldt's 2014 couch gags is one of the best in the storied series' history. It has everything you could want from a Hertzfeldt film—non-sequitir dialogue, satire, and unbelieveably sad portrayals of loneliness. I don't know what dark magic Hertzfeldt used to make this couch gag so emotionally potent, but it definitely worked.
7. Billy's Balloon (1998)
Billy's Balloon takes the tried and true formula of a boy and his sentient balloon and amps up the absurdity to eleven. There's nothing deep or introspective about this, it's just a hilariously brutal slapstick film about a little kid getting absolutely demolished by a sentient balloon. Extra points for the sound design, which is half of the humor here.
6. Genre (1996)
Hertzfeldt once again subverts a tried and true style—animator vs. animation—to wonderful effect. Genre is easily my favorite of his student films, it's riotously funny and the animation is incredibly well done. The writing isn't as insightful as a similar film like Duck Amuck, but the gritty student film vibe just adds to the charm and humor here.
5. The Meaning of Life (2005)
The Meaning of Life was when Hertzfeldt truly blossomed from satirical prankster into one of the most vital voices in film. The film was animated and photographed entirely by Hertzfeldt, so every single frame in the film was painstakingly drawn by Hertzfeldt, one by one. That would be an impressive feat even if the film itself was terrible, but it's not. It's visually stunning, oftentimes hilarious, and beautifully insightful and provocative.
4. World of Tomorrow Episode Two: The Burden of Other People's Thoughts (2017)
I might have to give this a little bit more time to properly sink in, because it's still so new and fresh, but the sequel to Hertzfeldt's 2015 World of Tomorrow stands tall with its fantastic predecessor. It's not quite as cohesive, but the humor is even more dry and biting, the narrative is more complex, the world is built upon even more, and it's just as emotional and existential.
3. Rejected (2000)
Even if you don't know this film, you definitely know all the lines from it. Every single absurd line here is infinitely quotable, and the advertisment parodies are so gleefuly absurd they loop all the way around into being bitingly satirical. Most importantly, Rejected was a perfect film for the turn of the millenium. It's absurd humor and simple animation style was undoubtedly influential upon a legion of internet animators, shaping the sense of humor of an entire generation.
2. World of Tomorrow (2015)
It's amazing that a writer/director who never even attempted science fiction before was able to create the most interesting science fiction stories in quite a long time. The world-building in this is phenomenal, Hertzfeldt manages to create a living, breathing, endlessly interesting world with only 17 minutes of screentime. Most importantly, he manages to create two incredibly interesting characters in Emily Clone and Emily Prime. Emily Clone's monotone voice clashes perfectly with the hyperactive energy of Emily Prime, and the former's emotional arc is painfully sad. Brilliant film that should have won the Oscar that year.
1. It's Such a Beautiful Day (2012)
It's Such a Beautiful Day is my favorite film of all time, without a single doubt in my mind. It floored me the first time I watched it and it has floored me every subsequent time I've watched it. The film is actually three short films stitched together, but it's entirely pointless to rank all three short films separately. Firstly, they're all so good I wouldn't know how to rank them. Secondly, they all work so much better when put together as a full film. The film follows Bill, a rather anonymous man living a menial life, as he struggles through an illness I can only perceive as brain cancer. The film's dry narrator (voiced by Hertzfeldt himself) chronicles every single aspect of Bill's life. His past, his future, his failed relationships, his slow mental decay, his work life, and his family's history are all analyzed with a proper amount of dry wit and an even heavier dose of insight and emotion. The second part of the film is one of the funniest things I've ever seen, the third part reduces me to tears every time, this is an absolutely brilliant film.
