The 8 Best Guest Stars On Brooklyn Nine-Nine

Since its premiere in 2013, the former Fox and now NBC sitcom Brooklyn Nine-Nine has had a very vocal fanbase, critical acclaim, and seemingly endless award recognition. While it may not have always been the most popular series in terms of ratings, B99 has always had what matters most: endless talent in both the writing and acting departments.

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You don't need to look much further than the series' main cast of regulars to find some pretty impressive resumes. Andre Braugher has been nominated time and again for Emmy awards for both dramatic and comedic work, and has won countless others. Andy Samberg is nothing short of a comic genius. Melissa Fumero and Stephanie Beatriz have become true inspirations to female viewers everywhere.

But the immense talent boasted by the series' cast doesn't end with its core group of regulars. Over the years, some incredibly famous guest stars have popped up for brief or recurring appearances, only elevating the already hilarious material they've been given in turn. Let's take a look at the eight best guest stars to visit the Nine-Nine.

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Katey Sagal as Karen Peralta in Brooklyn Nine Nine
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8 Katey Sagal (Karen Peralta)

Katey Sagal as Karen Peralta in Brooklyn Nine Nine

As one of the many examples of stellar guest casting on the series, longtime television legend and award winner Katey Sagal has recurred as Jake's mother, Karen. Raising him as a single mother after divorcing her cheating, absentee husband Roger, Karen is strong-willed and fiercely protective of her little boy - but entirely loving, too.

The character plays exactly into Sagal's wheelhouse of choice. After turns as Peg Bundy on Married... with Children and Cate Hennessy on 8 Simple Rules, Sagal has the role of independent sitcom mother down to a science, and brightens every scene in which she appears.

7 Jimmy Smits (Victor Santiago)

Jimmy Smits as Victor Santiago in Brooklyn Nine Nine

It isn't just Samberg's Jake who can boast some pretty impressive pedigree in the parent casting department. Jimmy Smits, best known for his award-winning roles on series such as L.A. LawNYPD Blue, and The West Wing, has appeared in the series as Amy's perfectionist detective father, Victor Santiago.

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Smits commands an intimidating screen presence, perfectly suited for the likewise commanding Mr. Santiago who primarily seems to exist in the series in order to intimidate the perpetually anxious Jake. But in addition to the powerful presence he exerts, Smits delivers pitch-perfect lines with impeccable comedic timing.

6 Sterling K. Brown (Philip Davidson)

Sterling K Brown as Philip Davidson in Brooklyn Nine Nine

Is there anything that Sterling K. Brown can't do? While fans of This Is Us undoubtedly know Brown best for his work as the all-around good guy Randall Pearson on the highly beloved series, Brown's turn as the dastardly Philip Davidson in the Brooklyn Nine-Nine bottle episode "The Box" allowed Brown to truly shine in a much different way.

While being interrogated for a homicide, Brown goes beat for beat opposite the series' resident powerhouse, Andre Braugher, never once letting up or letting anything slip - until Jake catches him in a web of his own making, in the end. But the cat and mouse game is electric, all thanks to the balance of manic comedy and steely reserve that Brown displays.

5 Nicole Byer (Trudy Judy)

Nicole Byer as Trudy Judy in Brooklyn Nine Nine

While Nicole Byer may be best known as the host of the truly delightful Netflix baking competition Nailed It!, a season six episode of Brooklyn Nine-Nine allowed her to truly show her comedic acting talent as Trudy Judy, the nefarious younger sister of longtime Nine-Nine favorite Doug Judy.

Trudy was revealed to be following in her older brother's footsteps, stealing cars here and there without a care in the world, and even going so far as to steal some identities, too. The sheer glee with which Byer portrays the verging on sociopathic younger Judy makes the character all the more enjoyable - as does the hinted potential of her eventual return.

4 Dean Winters (Keith Pembroke, AKA The Vulture)

Dean Winters as The Vulture in Brooklyn Nine Nine

Nowadays, Dean Winters is perhaps best known for his series of insurance commercials in which he stars as Mayhem, wreaking havoc wherever he can. And while The Vulture may arguably be on the right side of the law, there's no way to deny that he supplies his own fair share of mayhem along the way, especially when the Nine-Nine want him around the least.

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Winters' signature dry tone and gravelly voice make The Vulture impossible to ignore at any time, especially when he swoops in to not exactly save the day and hog all the credit for himself. But thanks to Winters' performance, The Vulture is somehow an entirely obnoxious character, while also managing to be consistently enjoyable and thrilling to watch.

3 Lin-Manuel Miranda (David Santiago)

Lin Manuel Miranda as David Santiago in Brooklyn Nine Nine

It's not every day that a super fan gets to help save a series from cancellation. It's also not every day that that same superfan eventually gets to guest star on the same show they helped to save. But it really isn't every day that this very super fan is Lin-Manuel Miranda, the genius behind Hamilton himself.

After contributing in large part to the Save Brooklyn Nine-Nine campaign in the spring of 2018, Miranda would go on to appear in a sixth season episode as Amy's brother - and casual nemesis - David. Even more of a perfectionist and goody two shoes than the do-gooder Amy herself, Miranda's David demands your attention every moment he's on screen, whether he's humble-bragging about his latest accomplishments or saving the day in a blaze of glory.

2 Jason Mantzoukas (Adrian Pimento)

Jason Mantzoukas as Adrian Pimento in Brooklyn Nine Nine

Whether you love him or you hate him, there's no denying that Jason Mantzoukas' true wild card of a character, Adrian Pimento, shook up the series just when things were starting to get a little too comfortable. After spending over a decade undercover in a mob investigation, Pimento is more than a little shaken up and unfit to return to work.

Nevertheless, he doesn't let anything stop him from getting in on the fun whenever he can - even if he goes more than a little overboard every single time. While his romantic relationship with Rosa may not have been the best idea, Adrian's character arc from outsider to part of the extended Nine-Nine family has allowed Mantzoukas to show himself to be a truly hilarious addition to the series.

1 Craig Robinson (Doug Judy, AKA The Pontiac Bandit)

Craig Robinson as Doug Judy The Pontiac Bandit in Brooklyn Nine Nine

Could the best guest star on Brooklyn Nine-Nine really be anyone else but The Pontiac Bandit himself, Doug Judy? Introduced in the first season, Craig Robinson's Doug Judy was immediately a scene stealer, the perfect nemesis for Samberg's Jake Peralta - except for the fact that, well, they're not really nemeses at all.

Sure, Judy may be an incorrigible criminal, stealing cars and running con jobs whenever he can. But he and Jake have developed a truly unique, unlikely friendship over the years, thanks to their shared outlooks on life, love of cheesy movies, and flair for dressing stylishly whenever the moment allows it. Doug Judy may be the great white whale of Jake's career in many ways, but he just might also be his best friend, too - a role that would never have worked without the entirely lovable Robinson.

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