Jake Peralta might show up to work every day like he just got injected with the spirit of Christmas in lieu of his doctor prescribed injection of Ritalin, but that doesn't mean he's super happy. In fact, all of the characters in Brooklyn Nine-Nine have a bit of edge to them underneath all of their office shenanigans, and I'm not just talking about the stress one must face having to do a show about "good cops" post-George Floyd.

But that edge is why we've decided to do a "who is the saddest" for Brooklyn Nine-Nine as part of our "Who is the actual worst?series. Now, this isn't the first time we've explored tragic characters on a TV series (we've done a "Who is the most tragic?" for Umbrella Academy and a "Who is the saddest?" for The Fairly OddParents); however, it is the first time I've been able to immediately narrow it down to one character. To me, the most obviously depressing character in all of Brooklyn Nine-Nine has to be Doug Judy, a.k.a The Pontiac Bandit.

This might be a surprising pick to some, as Doug Judy, like Jake Peralta, is all goofs all the time. Here he is singing a love song to the woman that might send him to prison rest of his life:

This is a guy who doesn't give a shit, right? Well, I'd say, wrong. I can tell you, as well as anyone else in comedy, as well as anyone with a copy of Webster's Big Book O' Cliche's That Happen To Be True, just because you're smiling on the outside does not mean you're smiling on the inside. Sure, maybe Judy's song is an ironic jab at his captor, or maybe, as I suspect, it's a heartfelt cry of unrequited love, shrouded in irony in order to protect Judy's hardened criminal image.

That doesn't seem like a guy with a minor crush. That's a guy who's fallen so hard for a woman that will never love him back (Reasons: Rosa's a cop and he's a criminal. Rosa is a lesbian and he's lesbiNot.) that it makes him sing the blues. Now, I can't tell if Rosa's unavailability is a feature or a bug within Judy's psychology. Perhaps, he loves her because she's unavailable to him as a means to protect himself, or maybe he just loves the way her unflinching, cold eyes glimmer in the moonlight. Either way, it's just one of Judy's many complicated relationships. 

There's also his connection with Jake. The pair refer to themselves as "frenemies," which is strange because Judy eventually asks Jake to be his best man in season 7 ...

... and there are only two reasons you would ask your frenemy to be your best man. One, you don't actually view him as your frenemy, but rather as your best friend. Two, you think he kinda sucks, but you still don't have any closer friends. However you slice it, it's a sad scenario. Judy's best platonic relationship is with a man who keeps arresting him. It's like if Les Miserables ended with Jean Valjean working up the courage to ask Javier to a ballgame.

And that's only scratching the surface of Judy's potential misery. He has a fiance now, sure, but there's no indication that he's gotten over Rosa, so he may very well be in a loveless marriage. He also lives a life of crime, which is not particularly stable in even typical circumstances but feels especially depressing in that he only steals Pontiacs. (A brand they literally stopped making a decade ago.) I can't imagine how sad this guy must be on the day-to-day, despite what he might show outwardly. But then again, I could be wrong.

Boyle can get pretty damn depressing.

Follow Dan on Twitter to learn more about his upcoming projects and find him on his podcast The Bachelor Zone to hear hot takes about all things in Bachelor Nation.

Top Image: NBCUniversal Television

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