The Best Brooklyn Nine-Nine Guest Stars, Ranked

One of the most delightful things about a long-running TV show is the slate of guest stars that often appear over the years. While most popular shows usually boast cool cameos and recurring characters, sitcoms are an especially fun format in which to see familiar (exciting) faces. Brooklyn Nine-Nine already has heavy hitters like Andre Braugher and Andy Samberg in its permanent ensemble, and plenty of its best episodes have been the ones that focus on the core cast, but it's still really delightful to see Jake, Holt, and the rest of the precinct get a little mixed up by a fun new character. 

It's difficult to choose the best of the best guest stars that have appeared on Brooklyn Nine-Nine over its eight seasons and even more painful to leave off iconic performers such as Dean Winters and J.K. Simmons, or underrated turns from up-and-coming actors like Karan Soni and Jenny Slate, but we had to draw the line somewhere. The following guest stars are some of the best and most memorable in "Brooklyn Nine-Nine," thanks in large part to their comedic chops and chemistry with the main cast. Make sure to read to the end of our countdown to see who topped the list.

Nasim Pedrad only guest stars in one episode as Jake's newfound sister Kate (Season 5, Episode 17, "DFW"), but she effortlessly inhabits the role and the quirky-but-lovable vibe of the show in a pretty short amount of time. Pedrad was also a cast member alongside Samberg on "Saturday Night Live" for a bit, and the two have a fun, energetic rapport in all of their scenes. Kate, who Jake only found out about because his father was loopy on pain medication after cutting off his thumb, is a bit of a disaster from the get-go, having been arrested on the flight from Texas to New York for vaping in the airplane bathroom. 

Jake is mildly horrified by her and her behavior, which is pretty funny considering how shocking some people find Jake's behavior a lot of the time. It seems that Roger Peralta (Bradley Whitford) definitely produces chaotic children, and Pedrad has a particularly shining moment in the episode when she drops some glass into her food at a restaurant and pretends to find it so she can get out of paying. It's too bad that we don't get to see Kate again on the show, especially since she and Jake end their visit on good terms with plans to stay in touch, but this episode alone is funny enough to land Pedrad a spot on the list of the best "Brooklyn Nine-Nine" guest stars.

Captain Jason "CJ" Stentley comes to the 99th precinct to serve as Holt's (Braugher) replacement while the former captain is hiding in Florida under the witness protection program. Ken Marino, who plays Captain CJ, is an underrated comedic actor with a gift for effortless buffoonery, and CJ is nothing if not a buffoon. At first, he's a pushover, saying yes to any request the detectives submit, and then, after Amy rallies the squad to ask CJ to be a better Captain and hold them accountable, he punishes them with the night shift when they go to Florida to help Holt and Jake despite being told not to.

Not only is CJ just a funny character and a fun addition to the precinct in Season 4 and Season 6's "Suicide Squad," where he works with the team alongside former Nine-Nine foes The Vulture (Winters) and Madelyn Wuntch (Kyra Sedgwick), but he's a pretty perfect example of a dumb dude that somehow just keeps failing upward. It's a little scary to think about all of the incompetent people out there who are tasked with life-and-death responsibilities, and those folks probably can't even carry a tune. 

Even though Sterling K. Brown is only in one episode of "Brooklyn Nine-Nine," it is widely considered to be one of the best episodes of the entire series, thanks in no small part to Brown's performance as murder suspect Philip Davidson. Season 5, Episode 14 ("The Box") takes place almost entirely in the precinct interrogation and observation rooms. Jake and Holt work together over the course of a night (they're only allowed to keep a suspect in interrogation for so long) to get a confession out of Philip for the murder of his dentistry practice partner. The point of this episode is to examine the relationship between Holt and Jake as fellow cops and mentor and mentee, but it wouldn't land nearly as well as it does if not for Brown's riveting performance.

Jake and Holt use many different tactics in interrogation to try and trick Philip. They do variations of good-cop-bad-cop and dumb-cop-smart-cop. Jake forces Philip to face his victim with a photo of the deceased, Holt tries to trigger Philip by insulting dentists, and Jake even lies at one point in hopes that Philip won't call his bluff. Just when it seems they will be forced to let Philip go without obtaining a confession, Jake tricks Philip by pretending to think that he just got lucky. Philip needs them to know how smart he is, and Brown plays the character's arrogance perfectly throughout the entire episode.

Even though Tim Meadows' cannibal killer Caleb is only in a few episodes of "Brooklyn Nine-Nine," he's highly memorable and one of the funniest guest stars that appear in the show. When Jake is framed for a crime and found guilty, he goes to prison where he shares a cell with Caleb. Aside from his tendency to eat humans, Caleb is amiable in general and helpful to Jake and is really Jake's only physically nearby ally as he goes through the most difficult months of his life in prison for a crime he did not commit. Nobody plays strange-made-normal like Meadows. Caleb often casually mentions his cannibalism to Jake during their time together, and some of the darkest humor in "Brooklyn Nine-Nine"  comes from how matter-of-fact he is about such gruesome crimes.

Later on in the series, after Jake has been released from prison, he and Charles visit Caleb at a new maximum security prison when they need help catching an organ-stealing serial killer. It's such a treat that viewers get a chance to see Caleb interact with Charles who is actually jealous of Jake's friendship with the inmate, even when Caleb attempts to bite Jake after helping him find a lead on his killer.

Kevin Cozner (no relation to Kevin Costner), is introduced in Season 1 Episode 16 ("The Party") as Captain Holt's beloved, fastidious husband who works as a classics professor. As Holt's husband, Kevin pops up a lot throughout the series in many short (but memorable) scenes, but he also has several episodes in which he shines as the MVP character. Kevin's relationship with Holt is both heartwarming and totally strange thanks to his and Holt's shared peculiarities (a love of obscure "jokes," overly formal interactions between intimate partners, a penchant for bird watching, etc.), and it's just really fun to watch most of the time.

Kevin's dynamic with Jake is also super fun. In Season 5, Episode 12 ("Safe House"), Jake and Kevin are forced to cohabitate for months in a police safe house after Kevin is threatened by crime boss Seamus Murphy (Paul Adelstein). Jake eventually coerces Kevin into watching almost every Nicolas Cage film that he has on DVD, and it's so funny to see Kevin demoralized by the boredom that forces him to watch movies he would never have otherwise even heard of. Kevin and Jake become good friends by the end of the show, providing an excellent layer to Holt and Jake's father-and-son dynamic.

No other guest star better personifies the lovable wackiness of "Brooklyn Nine-Nine" than Craig Robinson as Jake's nemesis-turned-best-friend Doug Judy. Doug appears in one episode of each season and the progression of his relationship with Jake is really fun to watch. At first, Doug is known as the Pontiac Bandit, a criminal that Jake has been trying to nab for years. After a few altercations though — wherein Jake and Doug find that they have a magical platonic chemistry — Jake can no longer hide his fondness for Doug, and their hijinks soon turn into partners in (solving) crime. 

Doug tops this list because of his final chapter with Jake. In Season 8, Episode 5 ("PB & J"), Jake takes Doug on a buddy road trip to prison (Doug had been arrested in New Jersey with an outstanding warrant from years ago), hoping to show him a great time before his incarceration. Doug, of course, has a plan to escape Jake and prison but has to put a stop to it when his hired crew tries to kill Jake. Later on in the episode, Jake gets a call from Doug who has somehow made his way to Amsterdam. It turns out Jake made sure Doug could escape prison, and it's a huge deal for him to break the law. Jake had never sacrificed the law for Doug before this point, despite their awesome friendship. It is a beautiful last adventure for the star-crossed best friends.