Brooklyn Nine-Nine’s Funniest Side Characters

Amy Santiago (Melissa Fumero) is always striving for perfection, from acing exams to ensuring her desk is always organized. “The Golden Child,” which aired in Season 6, explains that her drive for perfection comes from a need to outdo her brother, David, played by Lin-Manuel Miranda, a police lieutenant that aced the exam with a perfect score and once shot 10 bullets into the same hole. Even after getting his name cleared by Amy and Jake Peralta (Andy Samberg), David remains their mother’s favorite child, prompting Jake’s emotional and hysterical rant.

David only made one appearance, but his personality and demeanor go so far as to explain why Amy is….Amy….that he’s one of Brooklyn 99’s best characters, with the least appearances.

From one family member directly to another, just as Amy’s family shaped who she is, Roger Peralta (Bradley Whitford) helped make Jake the poorly adjusted adult that he is, much to the chagrin of the rest of the unit at Brooklyn 99. After walking out on his family when Jake was seven, Roger reappears in the Season 2 episode “Captain Peralta,” trying to mend the relationship with his son. Whitford’s deadpan delivery and completely insincere facial expressions make it so that everyone, but Jake, realizes that he really doesn’t care about his son.

At first, anyways, but as the series goes on and he keeps coming back, Roger Peralta becomes more and more supportive of Jake, mostly thanks to his relationship with Amy. Despite the character growth, Whitford still gets amazing laughs by veering into physical comedy and the grossest recurring gag of any character that’s not Adrian Pimento.

Cheddar the corgi, played originally by Stewart and then his sister, Stella, is the alpha dog of Brooklyn 99’s police unit. The pet of Captain Holt (Andre Braugher) and his husband, Kevin (Marc Evan Jackson), Cheddar makes frequent appearances, from Jake and Amy dog-sitting (which goes poorly) to participating in the annual Halloween heist. Every time, Cheddar is shown to be somehow smarter than most of the squad.

There’s a long history of dogs in sitcoms, most notably Eddie on Frasier, Comet on Full House, and Speedy on The Drew Carey Show. Cheddar keeps the tradition going strong, including a love of food-disrupting plans; in this case, it’s a wedding that goes horribly wrong in the most adorable way.

Captain C.J., which stands for “Captain Jason,” is the dimwitted replacement for Holt when he and Peralta are forced into witness protection. Ken Marino does a fantastic job playing a doofus that’s so annoying and so dumb that he makes Scully (Joel McKinnon Miller) and Hitchcock (Dirk Blocker) look competent. C.J.’s stories about how he got his position (A drug lord tripped over him) reveal he’s well aware about how underqualified he is, but he keeps lucking into major busts.

The heightened reality of Brooklyn 99 is always teetering on the edge of becoming a live-action cartoon, with C.J.’s self-awareness and dumb luck walking that balance beam with every appearance. It’s hard for everyone to get mad at him since he’s so laid-back and goofy, making him the oddest antagonist the squad goes up against during the entire series.

Fire Marshall Boone only appears twice in Brooklyn 99’s first season, which is a shame, as Patton Oswalt knocks his performance of the incompetent FDNY officer out of the park. Jake and Boone spend every scene sniping at one another, eventually escalating into a prank war. Yet nothing sums up Boone as well as the moment where he determines if a liquid is water or gasoline…by using a lit cigarette.

The second appearance of Boone is in one of Brooklyn 99’s best cold opens, at a football game between the NYPD and FDNY, which takes full advantage of Jeffords (Terry Crews, a former NFL star) being a bulldozer in a uniform. If any character needed to appear more, the hapless Fire Marshall that wasn’t afraid of going toe-to-toe with Peralta should have been a recurring “villain.”

“The Vulture,” brought to sleazy life by Dean Winters, earned his nickname from swooping in and claiming credit for closing cases. First appearing in Season 1, he returns later in Brooklyn 99’s third season as the new captain, promising to make life miserable for the unit. Obnoxious, egotistical, and sexist, The Vulture is everyone’s nightmare co-worker brought to life.

The character’s favorite color is “underboob,” he takes a chance with his dead brother’s hot wife and plays in a band. There are no redeeming qualities about The Vulture, which is, ironically, what makes his scenes so funny. After all, Rosa (Stephanie Beatriz) is attracted to him, and she only likes creeps (with a brief exception).

Kevin, the husband of Captain Holt, is played by Marc Evan Jackson, doing what appears to be a mockery of Andre Braugher’s stilted delivery. A college professor, Kevin intimidates most of the Brooklyn 99 squad with his intelligence, curtness, and snobbishness, though he eventually warms up to the department. As usual, it’s the wild exaggeration of an upper-class professor that makes Kevin’s appearances, or even just the mention of his name during Holt’s conversations, a constant source of laughs during the series.

Somehow, boring lines such as “Needled him a new suit.” Even when we’re fighting, you’re hilarious,” become awkwardly amusing when delivered by Kevin.

The wildest and craziest character on Brooklyn 99, Adrian Pimento (Jason Mantzoukas), was undercover for 12 years, and he’s having a hard time readjusting to life away from working for “The Butcher.” Claiming that every time he closes his eyes, he sees a new horror and blames dying of dysentery while playing The Oregon Trail as to why he doesn’t work with computers, Pimento’s lines can go wild places from one moment to the next.

Completely insane; there’s no telling how any scene with Pimento will go or what he’ll do, including shock proposals and running away in the middle of a sentence. It’s the unpredictability and how, even in-universe, he’s considered to be very weird that makes him one of Brooklyn 99’s best characters.

Madeline Wuntch (Kyra Sedgwick) has a long-standing rivalry with Captain Holt, the origins of which are finally explained at one point and then explained again with the real reason. Throughout the series, Wuntch, as police commissioner, makes life difficult for Holt as the only antagonist that truly gets under his skin. The result is every appearance giving Andre Braugher and Kyra Sedgwick an excuse to chew all the scenery in sight as they try to one-up each other.

Details of their relationship slowly come out, involving Derek Jeter and Michelle Obama, with each new revelation only making it better the next time Wuntch shows up at the Brooklyn 99 precinct. In her last appearance, Wuntch tries, a final time, to finally get Holt fired, and it’s one of the most satisfying ends to a recurring sitcom gag ever filmed.

Not just the best recurring character on Brooklyn 99, but the best in sitcom history, Doug Judy (Craig Robinson) is the infamous Pontiac Bandit, the arch-enemy of Jake Peralta. Every season, Judy appears, and every time, it’s one of the best episodes of the season. That’s because Judy and Jake end up becoming friends, eventually learning how much they have in common, from a love of pop culture (he couldn’t die because he was only on Season 2 of Game of Thrones) to juvenile humor (Judy creates a theme song after they team up).

Restricting Judy to only one episode a season stops the character from overstaying his welcome, making it an event every time he’s involved. From the change in his relationship with Jake over the course of the show to the recurring in-jokes between the two, Doug Judy is the greatest example of how to write a guest character.