3 Depressing Comedies You Need to Watch

Because who doesn't love to laugh while they're crying?

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This story originally appeared in the November 2017 issue of Jerk Magazine.

Sprinkle a healthy dose of tragic events and tear stricken characters, and any TV show can make you cry. But making you laugh with the same recipe, now that is hard—and we at Jerk respect intricate humor. From a talking anthropomorphic horse who is a well-known Hollywood actor to a rodeo performer who used to be a classically trained clown of all things, here are three of our favorite depressing comedies.  

BoJack Horseman 

Photo from Polygon

Photo from Polygon

Back in the 90s, he was the young star of a famous sitcom. Now he is largely forgotten and living on a concoction of alcohol and pills in his LA mansion—oh, and also he’s an anthropomorphic horse. The critically acclaimed Netflix original might be the most tragically beautiful show around. BoJack is a 50-something washed up actor, a self-sabotaging alcoholic and sex addict living in Hollywood with his roommate and best friend, Todd. Through a series of loosely connected misadventures, he struggles to fix the many mistakes haunting him from the past, come to terms with his broken relationship with his toxic mother, and most importantly find something, anything to fill the gaping hole inside him—while making you laugh. 

Fleabag 

Photo from Vulture

Photo from Vulture

This show follows a depressed, self-destructive woman who can’t relate to her family, hates her stepmother, and can’t recover from the mysterious death of her best friend. It may not sound like it at first, but it is one the funniest shows on TV. Phoebe Waller-Bridge, the star and creator, is the shows its beating heart. Slowly revealing just how broken her character—a sex addict plagued by bad habits and narcissism named Fleabag—truly is. You know how every white male comedian has a show that’s about how sad and weird their lives are? It’s something like that, but better. More than a comedy, Fleabag is also a deep and powerful tale about depression and regret. Waller-Bridge sneaks up on you, using comedy and tragedy to create something uniquely her own. 

Baskets 

Photo from The Daily Beast

Photo from The Daily Beast

Sad, bizarre, and surreal elements mix with dark humor in Baskets, which owes more to David Lynch than Chuck Lorre. Chip Baskets, a classically trained clown brought to life by Zach Galifianakis, becomes a rodeo performer after moving back home to Bakersfield, California and desperately wants to win back the affections of his mother. The show has its own rhythm and an acerbic, dry sense of humor that builds into something spectacular. You never get a sense that the show is making fun of Baskets or his mother, instead functioning as a delicate character study of two flawed people, which also happens to be fucking hilarious. It’s kind of perfect that a sad clown finally got a show that can make you laugh and cry in the span of 22 minutes. 

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