Brooklyn Nine Nine is one of the funniest sitcoms around thanks to its fantastic ensemble cast and just-broad-enough humour blended with almost-realistic cop show elements. But that great regular cast are supported by an equally brilliant array of recurring characters and guest stars. In this list, we’re celebrating the funniest of the show’s less often-seen characters, those guest appearances who’ve turned up once or twice to inject a fresh burst of comic energy into the show. Note that we’re not counting regular recurring characters like Adrian Pimento, Madeline Wuntch, or Kevin Cozner, aka Mr Raymond Holt. If they turn up more than once a year, or in more than three episodes in one season, they’re off the list.
12. Adam Sandler, played by himself in Operation: Broken Feather, Season 1, Episode 15
Adam Sandler’s appearance as himself in Season One is beautifully self-deprecating as well as funny. His deadpan delivery of “I’m a serious person” is hilarious in just the right way – of course the real Sandler is, presumably, as serious and as complex as anyone else, but he knows his own public persona and just how to play on it in the right way to raise a different kind of laugh. The interest in antiquities, the planned film about the Russian Revolution, it’s all funny – and somewhat undercut, even more amusingly, by his taunting of Jake straight afterwards. The whole scene did help to flush out a criminal though, so it wasn’t a total loss for Jake.
11. Geoffrey Hoytsman, played by Chris Parnell in two episodes in Season 2
When Jake’s lawyer girlfriend Sophia uses her boss as a transparent excuse to break up with him (by going on ‘pause’), Jake wilfully misunderstands and decides that the boss is the key problem, so he sets off to make the man like him. It all goes horribly wrong when Jake finds Hoytsman snorting cocaine in the bathroom, which Hoytsman claims he was doing accidentally while screaming loudly that Jake is arresting him to the whole room of lawyers. Sophia somehow still ends up blaming Jake – probably because she simply wanted to break up with him in the first place – and Hoytsman ends up returning to take Jake hostage and quite seriously threaten his life later in the season. Parnell’s over-the-top performance as a character who is, of course, high for much of the time, is what really sells the character. Funniest moment: Sniffing cocaine off his collar in the middle of the police precinct.
10. Jessica Day, played by Zooey Deschanel in The Night Shift, Season 4, Episode 4
Back in 2016, both New Girl and Brooklyn Nine Nine were active Fox sitcoms, so the network decided to do a crossover event in which the New Girl characters travelled to New York City and ran into the 99. Most of the crossover scenes actually ended up in the New Girl episode, but Zooey Deschanel’s character Jess Day did make a brief appearance in the otherwise stand-alone Brooklyn Nine Nine half of the crossover. While the New Girl episode provided a lot more context for Jess’s feelings about New York and her stress level surrounding Schmidt’s mom’s car and the soup she’s carrying, her appearance as an apparently slightly nutty woman who resists Jake’s attempts to commandeer the car is an entertaining interlude during the half hour. Funniest moment: Insisting that Jake’s oath to serve and protect applies to her soup.
9. Philip Davidson, played by Sterling K. Brown in The Box, Season 5, Episode 14
If this were a list of the show’s ‘best’ guest characters, rather than ‘funniest’, the top ranked would surely be Philip Davidson, played by Sterling K. Brown. ‘The Box’ is a tight, taught bottle episode that takes full advantage of Brooklyn Nine Nine’s hybrid status as both sitcom and cop show, and Brown’s Davidson forms a strong third of a triangle in this three-header with Holt and Peralta. It’s a really strong performance, but given that he’s playing a tough-to-crack murder suspect, not really the funniest, exactly. Still, he gets a good few laughs when appropriate over the course of a really engaging half hour of comedy/cop show crossover.
8. Karen Haas, played by Maya Rudolph in Coral Palms Parts 1&2, Season 4, Episodes 1&2
Maya Rudolph has a good line going in slightly weary authority figures (see also: The Good Place). Handling Holt and Peralta while they’re in witness protection is not an easy job and her exasperation at Jake’s refusal to accept his situation is well played. Haas is really funny, though, when she starts bringing her own issues into her official duties, clearly trying to get permission to cheat on her husband from someone, anyone – and Holt is happy to oblige. Funniest moment: Whoever it is she wants to sleep with is “really young” – something that clearly shouldn’t be funny, but the face Rudolph pulls as she says it is what sells it.
7. Lin-Manuel Miranda as David Santiago in The Golden Child, Season 6, Episode 9
Miranda is marvellously smarmy as Amy’s too-perfect brother, her demanding parents’ favourite, who snubs popular culture and shows off by saving people’s lives (including Amy’s own husband). Amy’s delighted reaction when he’s arrested for cocaine possession and deep disappointment when he turns out to be innocent are highlights, but the funniest scene by far is the dance-off between David and Amy, in which both comprehensively demonstrate that dancing is not among the Santiago family’s many strengths. Funniest moment: David thinks elbows should form a bigger part of a dance routine than they really should.
6. Frederick, played by Nick Offerman in Ava, Season 3, Episode 8
Any time we meet Captain Holt’s friends and family, many of whom share his stoic, Vulcan-like demeanour, it’s always hilarious. JK Simmons as his old friend Dillman very nearly made the list, but he was just pipped to the post by Ron Swanson – sorry, Nick Offerman – as Holt’s ex-boyfriend. There’s a lot of crossover between Parks and Recreation and Brooklyn Nine Nine among the cast and crew and Offerman isn’t even the only Parks & Rec alumnus to appear on this list, but he’s probably the one whose appearance most quickly calls to mind his earlier character. The idea that Holt’s ex-boyfriend is Ron F-ing Swanson is just genius. OK, Frederick lacks Swanson’s magnificent moustache (though he has a glorious beard) and he’s even more brusque and stand-off-ish, but he’s a perfect match for Holt, even more in their post-break-up mutual antagonism than we imagine they were in their relationship.
5. Mark Devereaux, played by Nathan Fillion in Serve & Protect, Season 4, Episode 14
It’s always funny any time police characters in a cop show visit the set of a TV cop show, and for added meta humour, in this case the actor playing the fictional detective is played by an actor who works on a cop show (albeit as a non-cop character). Phew! That’s a lot of layers of meta. Nathan Fillion’s pompous star who apparently thinks playing a detective makes him a detective is very funny, and it gets better when it turns out that was a ruse to cover up his own petty criminal activity before he folds like wet paper. It’s just a shame we didn’t get to see more of him. Funniest moment: Devereaux tries turning on the angry detective act from his show to cover up his own crime, only to be confronted with quite a lot more than a “shred” of evidence and fold immediately.
4. Eleanor Horstweil, played by Kathryn Hahn in Hostage Situation, Season 3, Episode 11
We heard a lot about Boyle’s ex-wife over the first couple of seasons, partly because Boyle was still living in her basement, hanging out with her new husband Hercules. We knew what sort of person Eleanor was when Boyle explained that he gets the beach house from December to February. When we finally meet her in the flesh, Kathryn Hahn does not disappoint – Eleanor is surely one of the most purely horrible characters we’ve seen on the show (and yes, we’re including all the murderers). She hits a 90-year-old priest with her car and then destroys Boyle’s frozen sperm, all with no apparent sense of guilt, and she largely gets away with it, too. But she does it all with a perfectly deadpan expression and carefree attitude, each horrifying act funnier that the last. Funniest moment: She goes further than Jake ever thought she would when she “shoots a hostage” – i.e., throws some of Boyle’s sperm down the drain.
3. Seth Dozerman, played by Bill Hader in New Captain, Season 3, Episode 1
Bill Hader’s screentime on the show is relatively brief, but he is hilarious from start to finish, attacking the squad with every shouted command like he’s firing metaphorical bullets at them. It might actually have been really cool to see the squad try to deal with him as their Captain for more than one episode, with his extremely demanding requirements and very highly strung personality, but on the other hand, perhaps this is a joke that works better in small quantities. Any character whose dying words are “Tell my wife I love her work ethic” is probably a character better enjoyed for a shorter period of time.
2. Caleb, played by Tim Meadows in three episodes in Seasons 5 and 6
Jake is shocked to discover his only friend in maximum security prison is a cannibal (though he would prefer to be identified as a wood-worker), having assumed everyone in protective custody was a wrongly accused police officer. Caleb is surely Brooklyn Nine Nine’s best streak of really, really dark humour – not only did he murder and eat nine and a half people, they were small children too. Every reference he makes to his “nightmare” past is sickly hilarious, and gets worse and worse every time, including a reference to his “skin suit”. But he really does care for Jake, even if he still kind of wants to eat him. The sheer audacity of the black humour surrounding this character is fantastic and always funny. Funniest moment: Caleb shows that he has a softer side when he saves Jake’s life – but he immediately deeply regrets it and would not do it again.
1. Doug Judy, played by Craig Robinson in multiple episodes (one episode or two-parter per year)
Yes, we carefully defined a recurring character as someone who is either in more than three episodes or who appears more than once a year specifically so that we could include Craig Robinson‘s Doug Judy. It’s our list and we make the rules. There’s something twistedly beautiful about Jake and Doug Judy’s tender but tense friendship, even in the early years when Judy is constantly double-crossing poor Jake. The two of them have perfect comic chemistry, and each running gag in their friendship, especially their fondness for swaggering out in a new outfit or disguise, just gets funnier and funnier. Long may Doug Judy continue to turn up roughly once every twelve months to harass his long suffering best friend.
