Chekhov's Gunman


Top Ten Depressing Comedies- A Mexican Standoff

“Tragedy is when I cut my finger. Comedy is when you fall down a well and die.”- Mel Brooks (probably, who knows if I can trust the Internet)

I don’t quite know what draws the line between comedy and tragedy- jokes I suppose- but I do know that the two intersect more often than you’d think, and I simply can’t pass up the opportunity to use a Mel Brooks quote.

Comedy and tragedy have a closer relationship than we initially believe. There’s a reason we find out later on that many of our favorite comedians suffered greatly with depression. Behind all good funny, there’s something inherently sad. Here’s a list of items that lets the sad shine through a bit more than normal…

Community Troy Birthday

10) Community Season 2 Episode 10- “Mixology Certification”

There’s something inherently depressing about the holidays. Something covered very well in the Glee Club episode in Season 3 is that “Trying to force the holidays to be bright just makes them that much darker.” Now, “Mixology” wasn’t the Christmas episode in its season, and this spot very easily could have gone to its Claymation running mate “Abed’s Uncontrollable Christmas,” but it aired close enough to the holiday and so well captured the sorrow that many of us feel around that time that it so, so easily could have been. This was the episode where Troy finally had to become a man when everyone else around him was too drunk or self-involved to help each other out. It’s an inherently sad and brilliant episode (and my personal high water mark for the entire series).

Wet Hot American Summer Christopher Meloni Gene

9) Wet Hot American Summer

You wouldn’t expect a movie so concerned with the bathing habits of adolescent Jewish DJs to make a list of depressing things, but you’d have expected wrong because I am going to awkwardly shove in references to Wet Hot wherever possible. The film is an endlessly rewatchable comedic romp up until the last minute or so, when we are greeted as an audience with one breathtakingly honest blow that struck a very tender place for all the lads who great up being “nice guys.” It’s a beautiful touch of heart at the end of one of my personal favorite comedies.

“I have yet to see The Godfather- Part II but you bet your ass I’ve seen Wet Hot American Summer eight times.”- Me

Scrubs My Old Lady

8) Scrubs Season 1 Episode 4- “My Old Lady”

Scrubs could have any number of episodes on this list, and this one had to fight tooth and nail against the one that ends with a dying lady singing “I’m Waiting for my Real Life to Begin.” But I decided to go with “My Old Lady” not because it’s so memorable (although it is) but because it was the first episode- and so early in the show’s run- to really go straight for the heart, throw in a gut punch, a Hail Mary. It set a tone and theme of loss and death that would haunt Scrubs throughout its run and come back in some of its greatest moments.

Fargo Marge

7) Fargo

Calling the Coen Brothers films “Comedies” is a lot like calling a cow “Burgers”: It’s true, but there’s more to it than that. That being said, Fargo and its funny accents are unmistakably one of the darkest comedies of all time, one that happens to be about betrayal and loss and corruption as much as it is about funny accents. The accents are funny, but standing tall in the face of unbelievable evil and withholding your faith in humanity is usually less so.

Bill Murray Groundhog Day

6) Groundhog Day

If you only watched the ads for this film, you’d think it was a funny romp about gophers that casts Bill Murray as Kenny from South Park. And that’s mostly true… for the first half. The second half, however, is often called (by me) “The Transition into Sad Murray.” The last half of Groundhog Day sees Murray’s character Phil turn into a suicidal, repentant man of learning who has lived for an untold number of centuries, reliving the same day over and over again. He has reached a kind of madness rarely reserved for mainstream comedies.

Hitchhiker's Guide to the Galaxy Don't Panic

5) The Hitchhiker’s Guide to the Galaxy franchise

As absolutely gut-bustingly hilarious as the Hitchhiker’s franchise is, it also stands as the most accurate gateway I’ve seen into the mind of a brilliant cynic. The first book opens with the destruction of Earth and everything protagonist Arthur Dent has ever known. Thank God his life was so lonely and pathetic beforehand, else that would have been really depressing. And speaking of God, He undoes His own existence in Chapter Six. By book two, we see a man undone having his faith in the ruler of the universe shattered by the ruler himself being an incredible letdown. Not to mention that the second book sees the Universe ending multiple times and the continued plight of Marvin the Paranoid Android.

A Skull in Connemara

4) A Skull in Connemara

The collected works of writer/director Martin McDonagh (In Bruges, Seven Psychopaths) could have a real shot at the Depressive Anthology award if there was one, and they also make the writer in me froth at the mouth with pure, unbridled lust and reverence. Long story short, I love them. But they are also all unabashedly depressing. Connemara tells the story of an Irish grave digger forced to dig up his dead wife’s grave. And it only gets more depressing from there. Hilariously, devastatingly depressing. Read this play.

Also, watch In Bruges. I mentioned it in my very first post and will not shut up about it until I know that all of you have seen it.

Party Down

3) Party Down

Whereas Community and Scrubs only got one episode on this list, Party Down gets to be honored for the whole shebang. Besides featuring one of the best ensemble casts in television history, it also has a series-long theme that can roughly be surmised as “Sometimes you just have to give up on your dreams.” We are bonded to the members of Party Down Catering through their misfortune, but it also makes us really, really sad. Now, quickly, in your sorrow, fashion Adam Scott an Emmy out of anything and everything you can find. We need to Apollo 13 Adam Scott a statue.


2) Catch-22

If you’re not paying attention while reading this hilarious novel about a squadron in World War II, you may miss that it very casually but very repeatedly features depictions of rape and dismemberment. Like many real people, the book uses humor as a defense to fend off the encroaching fear of being shot at by people you don’t even know.

Honorable Mention: MASH, because it is MASH and it’s great.


1) Louie

Lawdy, I’m sad just thinking about this show. I also really, really want to watch it. The Tiger Woods of constructed depression, there is hardly an episode of Louie that won’t make you want to curl up into a sad little ball and suck the thumb of whoever is closest. Episode topics include such child-friendly material as sexual inadequacy, death and loss, and innumerable shots of Louis C.K. looking lonely. The show started out as a comedy, but about the time an episode revolved around the crisis of faith of a nine-year-old, it made a sharp left turn into “A Series of Superb Short Films by Louis C.K. that are Occasionally Funny.” My personal favorite episode is about masturbation, perhaps the most depressing activity one can watch Louis C.K. do on Netflix.

Chekhov’s Gunman is a film and television blog moderated by Kevin Lanigan, a future writer of great movies and TV. At least my girlfriend thinks so. Keep checking back every week for another of these Mexican Standoffs, as well as reviews of Community and Game of Thrones, and our Good Stuff. You can find Kevin on Twitter if you’re feeling up to it.

Never give up, never surrender…


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3 thoughts on “Top Ten Depressing Comedies- A Mexican Standoff

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