Top 20 Best Brooklyn Nine Nine Cameos

A member of the prolific Wayans family, Damon Wayans Jr. is best known for appearing on shows like “Happy Endings” and “New Girl,” the latter of which makes for some interesting continuity issues. But more on that later! Wayans Jr. plays Stevie Schillens, Jake Peralta’s first partner from when the two of them were beat cops. A reunion leads to the two of them gelling and reminiscing about old times, frequently breaking into improvised raps. While Jake’s buddy Charles Boyle is jealous, he also discovers that Schillens is a dirty cop after he plants drugs at a suspect’s house. If the show could get him back somehow, maybe that would “un-break our hearts.”

The first “SNL” alumnus on our list, Jenny Slate is also notable for her voiceover work. In “Brooklyn Nine-Nine,” Slate plays Bianca, the mistress of mobster Freddy Maliardi. Jake hears the mobster is hiding out at his mistress’ place and confronts her there. Although she first holds him at gunpoint and is then uncooperative, Bianca eventually gives up her former beaux when she learns he was cheating on her with her sister. It’s a small but crucial role for the episode and one that Slate clearly has a lot of fun with.

Doug Judy may not make our list, but his sister Trudy Judy does! Played by Nicole Byer, a comedienne known for her bake-off show “Nailed It!,” Trudy is quite similar to her brother, going so far as to copy his signature crime – stealing Pontiacs. She’s also prone to betraying Jake to evade justice, just like her sibling. Trudy is more than just a female version of the Pontiac Bandit, though, as her flamboyant and confident sexuality gives her a flair all her own. While she’s only appeared a few times thus far, given her brother’s reformed ways, it’s possible she’ll continue to appear.

This actor of “Lord of the Rings” and “The Goonies” fame is a self-professed fan of the show; tweeting about its cancellation by FOX. Thankfully, not only was the show saved by NBC, but Sean Astin also wrangled a role of his own on “Brooklyn Nine-Nine.” Astin plays Sergeant Knox, a tech expert called into the precinct after it’s hacked. With a ticking clock, Knox pressures Captain Holt to erase the servers. Yet, Amy discovers that Knox is actually the perpetrator and is attempting to use them to destroy evidence of an earlier crime he committed. From fan to show foe!

Another former “SNL” alum, Tim Meadows plays Jake’s prison cellmate and friend, Caleb. Although amiable and friendly, Jake is horrified to discover that Caleb is a cannibal. Nevertheless, as one of Jake’s few allies inside, Caleb is indispensable during the detective’s time served, even taking a knife for him. That doesn’t stop him from getting a little bitey, though, such as when he returns to assist Jake with a case. Meadows manages to make Caleb’s congenial attitude contrast hilariously with his disturbing interests, making for a wonderfully entertaining and kind of scary character.

Doug Judy and Jake Peralta may begin as bitter rivals, but their bromance grows as time goes on, to the point where Jake attends Doug’s bachelor party. Held in Miami, the guys take a private jet lent to Doug by Mark Cuban, the billionaire host of “Shark Tank,” playing himself. It’s a short scene, but in it, we learn that Cuban had Doug on his show to pitch a noise canceling blanket for “intimate relations” called the “Smush Shush.” Does anyone else want to see that episode of “Shark Tank?”

This comedian, best known for creating and starring in shows like “Big Mouth,” appears in an episode where the 99 is invited to participate in a mock hostage situation in a multi-agency training exercise. Kroll plays Kendrick, an arrogant Homeland Security agent who immediately gets on Jake’s nerves. After Kendrick assigns the precinct to be the hostages, Jake leads a rebellion and they become the hostage-takers, eventually culminating in a showdown between him and Kendrick. Kroll does a great job making the snarky DHS agent both funny and easy to dislike.

An actress and comedienne known for films like “Bad Moms,” Kathryn Hahn plays one of “Brooklyn Nine-Nine”’s worst characters, Charles’ ex-wife, Eleanor Horstweil. Oft-mentioned but only seen once, Eleanor manipulates and torments her former husband. In her thus far only on-screen appearance, Eleanor takes Charles’ sperm hostage after learning he wants to use them to have a child; attempting to use them as blackmail in order to get him to have charges against her dropped. It’s a testament to Hahn’s skill as an actress that we hate Eleanor as much as we do. Then again, anyone who treats poor Boyle so much was bound to earn our ire!

Jake and Captain Holt being forced into witness protection isn’t all bad – it gives Andy Samberg an opportunity for an “SNL” reunion! His former castmate Maya Rudolph appears as Marshal Karen Haas, the duo’s contact with witness protection. Haas is insistent on maintaining the minutiae of their cover identities. She also calls a meeting that gets strangely personal, as Haas asks their advice in a roundabout way for her to cheat on her husband with a younger man. Rudolph’s absolute commitment to the character’s ridiculousness is a real treat.

A famed rapper and actor, Kid Cudi shows up early in the show’s history, as Dustin Whitman, a recently paroled convict that Jake put away, whom he suspects is up to his old tricks after a robbery with the same M.O. occurs. Unfortunately, Jake arrests him without enough evidence, giving the team only 48 hours to prove his guilt. As it turns out, Whitman taught his former cellmate how to do it and gave himself an alibi; leading to his arrest. Kid Cudi plays Whitman’s smug superiority well and acts as a great foil to Jake’s antics.

Most of the cameos on our list are of celebrities playing themselves or original characters. However, in this instance, we have a character from another show. Zooey Deschanel appears in a crossover event between “New Girl” and “Brooklyn Nine-Nine” as Jess Day. Although the “New Girl” half of the crossover is much more extensive, only Jess appears in the “Brooklyn Nine-Nine” episode, in which her car is briefly commandeered by Jake while pursuing a suspect before he crashes it soon afterward. It’s a short but sweet cameo that we enjoy every time.

In a nice bit of meta-humor, Nathan Fillion, an actor known for appearing on cop shows like “Castle” and “The Rookie,” appears as an actor on a cop show within the cop show “Brooklyn Nine-Nine.” Everybody follow that? Fillion plays Mark Devereaux, an actor on the “Law & Order”-like “Serve & Protect,” who injects himself in Rosa and Jake’s investigation into the theft of a laptop on the set. Devereaux’s hapless belief that he can do their jobs because he plays a cop on TV is hilarious, and also acts as a good red herring, since it turns out he’s the culprit responsible.

Another “SNL” castmate of Andy Samberg’s, Fred Armisen makes several cameos as a bizarre foreign man from a fictional country named Mlepnos. Encountered by Jake and Amy several times while canvassing doors, Mlepnos has a number of odd qualities, such as spelling his name with a silent “clay” or singing songs about a dog’s loss of virginity. He even makes an appearance at Jake and Amy’s wedding playing the violin, although he claims not to know either of them. Armisen’s shy and weird demeanor helps make the minor character very memorable.

Best known for his work composing and starring in the musical “Hamilton,” Lin-Manuel Miranda guest starred on “Brooklyn Nine-Nine” as Amy Santiago’s brother, David. Much like his sister, David is a chronic overachiever and is even less humble than Amy is. Naturally, this drives her nuts, leading her to be happy instead of upset when David is framed for cocaine possession. While trying to clear his name, the two of them remain competitive, but they eventually become closer. We just wish David had gotten a chance to sing and show off Miranda’s impressive pipes.

A dry comedic actor most famous for his time as Ron Swanson on “Parks and Recreation,” Nick Offerman also deadpan funny on this show too. Offerman plays Frederick, an OB/GYN and Captain Holt’s ex-boyfriend. When Terry’s wife goes into labor at the station, Jake, in charge of the delivery due to Terry’s absence, forces Holt to try to reconcile with Frederick to gain his assistance. The disappearance of a wooden duck apparently led to their breakup, though we can see Holt’s attraction in the first place, given that glorious beard…

Yet another ex-“SNL” cast member, Bill Hader has amazing range and he delivers an intense performance as Holt’s temporary replacement, Captain Seth Dozerman. Perhaps even more serious and productivity-focused than Holt is, Dozerman has a cardiac event within minutes of introducing himself to the squad. This barely slows him down, though, as Dozerman continues making draconian attempts to increase efficiency around the precinct, even briefly bonding with Jake over it. However, catching Jake and Amy kissing in the file room sends him into a full-blown meltdown that gives him a fatal heart attack. As much as we would’ve loved to see Bill Hader appear more in the series, we don’t think our hearts could take it.

J. K. Simmons has had a long career, during which he’s appeared in pretty much everything, so it was only a matter of time before he showed up on “Brooklyn Nine-Nine.” When an apparent prank gone wrong explodes on Jake’s desk, Holt calls in his experienced detective friend, Frank Dillman, to solve the “who has done this” that ensues. Seemingly unflappable and able to deduce everything about someone just by meeting them, Dillman pins the blame on Jake after finding a receipt for the materials in his bag. However, Jake then proves that Dillman framed him, as he’s no longer even a detective and now works at Yarn Barn.

Jake Peralta loves “Die Hard.” This is no secret. So Jake is thrilled when he learns from Charles Boyle that actor Reginald VelJohnson, who played Sgt. Al Powell in “Die Hard,” was a part of his bachelor party, with the actor playing a fictional version of himself. Unfortunately, Jake skipped out on that part of Boyle’s carefully constructed evening, leading him to turn to VelJohnson for help when Charles leaves after finding out they cheated. VelJohnson’s dislike for Jake for not showing up builds to the point where he considers him an enemy for life and is willing to badmouth him to Jake’s idol, Bruce Willis. (Now there’s a cameo we need!)

Known for his work on the drama “This Is Us,” among other roles, Sterling K. Brown made a dramatic impact on “Brooklyn Nine-Nine” during his singular appearance on the sitcom. Brown plays Dr. Philip Davidson, a dentist suspected of murder who is interrogated by Captain Holt and Jake throughout an entire episode. Davidson is smugly superior and always seemingly a step ahead of them both. Eventually, though, Jake is able to play on his pride and get him to fess up to the murder. He may be just sitting at a table, but Sterling K. Brown still manages to make Davidson one of the show’s most effective one-off antagonists.

Before we get to our top pick, here are a few honorable mentions:

Mario Lopez
Biggest Celebrity Snub?

Pete Davidson
Pre-SNL Fame

Neil deGrasse Tyson
Just When You Thought the Guy Couldn’t Get Any Cooler…

Nasim Pedrad
Jake’s Con-Artist Sister

Paul Rust
His New Album Is Called “E-ska-ape Plan”

Yet another “SNL” alumnus and a frequent collaborator with Andy Samberg in movies, Adam Sandler makes a cameo in “Brooklyn Nine-Nine” playing himself. While trying to spot a suspect in a crowd, Jake switches places with an auctioneer and is heckled by Sandler after he does a poor job of pretending to auction off items. Although Sandler has most of the crowd behind him through the exchange, Jake’s crack about Sandler’s Russian Revolution movie featuring Kevin James is definite gold… particularly since it’s true. We have to wonder who Sandler himself would play – Lenin or Stalin?