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I'm Thinking of Ending Things

Like with Wes Anderson films, you know a Charlie Kaufman movie when you see one. And this may be even more impressive in regards to Charlie Kaufman since more than half of his films weren’t even directed by him. They’re from his screenplays, as it’s his writing that always stands out. It’s not so much his voice as it is his themes and labyrinthine storytelling. Case in point, his latest movie, I’m Thinking of Ending Things, is based off of a novel, but still distinctly fits in with the kind of cerebral films that the writer/director has been known for over the years.

In truth, Charlie Kaufman is probably the only modern day screenwriter who could get a list of this sort just from his writing alone. Now, granted, Charlie Kaufman is not for everyone, and some of his movies are so far out there that I probably wouldn’t recommend them to anybody I know. But for that rare person who is genuinely interested in getting lost in a movie, then there’s no better storyteller in Hollywood than Charlie Kaufman. Here are his best films, both written and directed, ranked.

Sam Rockwell with the gun

8. Confessions of a Dangerous Mind (2002)

Even though Charlie Kaufman doesn’t particularly like George Clooney’s directorial debut, Confessions of a Dangerous Mind, is still a pretty good movie. It follows The Gong Show host, Chuck Barris (played by Sam Rockwell) and his double life as a CIA assassin.

Confessions of a Dangerous Mind is a pretty enjoyable film, but it’s definitely the least Kaufman-esque movie on this list. This seems to be by design since George Clooney apparently changed up the script quite a bit, which is why Kaufman isn’t particularly fond of this film. So, while it’s a decent movie, it’s kind of bland in its delivery and mostly devoid of Kaufman’s cerebral storytelling, which is more to its detriment than its benefit.

Patricia Arquette up front

7. Human Nature (2001)

Michel Gondry’s first film (the director and Kaufman would work together again on a much more beloved film), Human Nature is weird, but not so much in a good way. It’s a story about a woman named Lila (played by Patricia Arquette) who grows hair all over her body and returns to nature to be sexually liberated. She ends up writing a book about her experience and eventually meets a sexually repressed scientist (played by Tim Robins), as she’s looking for a mate. They both discover a man raised by apes (played by Rhys Ifans), and the scientist tries to condition him to adapt to society. But it’s hard, since it’s nigh-impossible to overcome one’s human nature. The scientist shocks the man ape every now and then with a buzzer to prevent him from humping things. It’s somewhat humorous.

Human Nature definitely feels like an entry-level Charlie Kaufman film, but its comedy feels like it misses the mark more often than it hits it. The characters are all really silly, which may be more because of Michel Gondry’s directing-style rather than Kaufman’s writing. But if you want to gently introduce somebody into the world of Kaufman, then there’s a far better Gondry/Kaufman film to steer them in the direction of.

Philip Seymour Hoffman up front

6. Synecdoche, New York (2008)

Charlie Kaufman’s directorial debut, Synecdoche, New York is the most Charlie Kaufman movie ever made. Starring Philip Seymour Hoffman, Synecdoche, New York is about a theater director who commits to a production so deeply that it eventually takes over his life. He also creates his own little world inside of a warehouse. That’s the best I can explain it, because honestly, this is the most existential movie you will ever see in your entire life, and that’s putting it lightly.

Famed movie critic, Roger Ebert, once called Synecdoche, New York the best of movie of the decade. And I can only attribute that to the fact that he was much smarter than I’ll ever be. I said earlier that Kaufman is known for his labyrinthine storytelling, and this movie is the clearest example of that. You can get so lost in this movie that you almost forget that you’re even watching a movie, which I guess is the point. It’s an audacious film, to be sure. Just not a very clear one.

Anomalisa

5. Anomalisa (2015)

I’m sure there’s a perfectly rational reason for why Anomalisa had to be a stop-motion film (and I just love that it was up against children’s films like Inside Out and Shaun the Sheep Movie at the 2016 Academy Awards), but I’m not entirely sure what it is. It’s the story of a an extremely lonely man named Michael (voiced by David Thewlis) who sees everybody in his life as looking and sounding exactly the same (all voiced by Tom Noonan). This is all part of what is known as the Fregoli delusion, which is a real disorder where people believe that everybody is the same person. Things are awful for Michael until he meets a woman in a hotel who actually looks and sounds different (voiced by Jennifer Jason Leigh). But since this is a Charlie Kaufman film, things of course don’t end well.

Anomalisa has an interesting concept, but it’s surprisingly played straight. Despite its plot, it’s a story that anybody can relate to since it’s entirely human to feel completely alone at times. This one is actually one of Kaufman’s hardest films to process because of all the real emotions running through it.

Jessie Buckley standing up

4. I’m Thinking of Ending Things (2020)

The most recent film on this list, I’m Thinking of Ending Things is based on a novel of the same name, but could just as well be a Charlie Kaufman joint. The story is about a woman (played by Jessie Buckley) who is thinking of ending her relationship with her boyfriend (played by Jesse Plemons) on the way to visiting his parents on their farm. But it’s also quite scary, and most of it takes places in a car to and from the farm. Plus, the protagonist may not be who you think it is. Because of course it isn’t.

While there are a few deviations from the book (mostly in the ending), Charlie Kaufman deep dives into the minds of his characters like no other writer/director. It seems like a fairly simple story, but it turns super subversive, and creepy because of it. It’s the kind of film where you need to watch and re-watch it just to catch every little detail, and even then, you might not grasp all the different character dynamics all throughout the film.

Jim Carrey on the left, Kate Winslet on the right

3. Eternal Sunshine of the Spotless Mind (2004)

The other Charlie Kaufman/Michel Gondry project, Eternal Sunshine of the Spotless Mind is undoubtedly Charlie Kaufman’s most popular film. Starring Jim Carrey and Kate Winslet as a couple going through a tough break-up, the movie poses this question: If you could medically forget somebody’s existence, would you do it? And if so, what ramifications does that have on the person who’s being forgotten? There really aren’t any easy answers for that in this movie, nor should there be.

Eternal Sunshine of the Spotless Mind is probably Kaufman’s most accessible movie. The concept is out there, but it’s easy enough to digest, and the plot is relatable. It’s not his most interesting film, but it’s probably his most complete.

John Cusack

2. Being John Malkovich (1999)

Being John Malkovich was the debut movie for both Charlie Kaufman and filmmaker Spike Jonze, and what a debut! It’s about a puppeteer (played by John Cusack) who finds a door that leads into John Malkovich’s head. He and his wife, Lotte (played by Cameron Diaz with frizzy hair!) realize that anybody can go through the door, and she goes through as well, realizing that she likes women and creating a sort of love triangle with a woman named Maxine (played by Catherine Keener) and John Malkovich. It’s bizarre, but in all the best ways.

When I think of Charlie Kaufman, I think of Being John Malkovich. Its story is perplexing and existential, but also enjoyable throughout. The concept is something only Charlie Kaufman could come up with, but it’s never really dark or nihilistic like some of his later stories. It’s fun and audacious, and you feel like you’re along for the ride. It’s a safe, enjoyable Charlie Kaufman film that I can recommended to anybody, no problem.

NIc Cage in the seat and on the floor

1. Adaptation (2002)

I’ll tell you, Charlie Kaufman and Spike Jonze make a really great team. In Charlie Kaufman’s best film, Nicolas Cage plays Charlie Kaufman and Charlie Kaufman’s fictional brother, Donald. Charlie Kaufman is adapting the real book, The Orchid Thief, but has severe writer’s block, while his brother, Donald, is a budding screenwriter who wants to write banal action fluff that eventually makes its way into the climax of the film. It’s super meta, but in a way where you don’t feel excluded from the actual story, and even feel a little smart for being able to follow it completely. Meryl Streep and Chris Cooper also fill in key roles.

Adaptation is Charlie Kaufman’s funniest film, and all the better for it. I love movies like Anomalisa and I’m Thinking of Ending Things, and Charlie Kaufman is a really talented director, but I feel like he gets a little too dark when he has complete creative control. Adaptation is the perfect mixture of Kaufman’s cerebral storytelling, and Spike Jonze’s often off-beat approach to his direction. So, Adaptation is a mindbender, but an approachable one. It might not be the Kaufman devotee’s favorite film (that would likely be Synecdoche, New York), but when it comes to all the plusses and none of the minuses of Charlie Kaufman’s oeuvre, you would be hard pressed to find a better movie of his than Adaptation.

Charlie Kaufman is still one of the most fascinating writers in Hollywood today. You never go into a Charlie Kaufman movie knowing what you’re going to get, and that’s a good thing. But what’s your favorite Charlie Kaufman movie? Sound off in the comments.

What is your favorite Charlie Kaufman film?
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