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aion-rsa · 3 years

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Brooklyn Nine-Nine’s Funniest Guest Cast Characters

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Warning: contains Brooklyn Nine-Nine spoilers.

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.

Funniest moment: Admitting his “serious” Russian Revolution film features Kevin James as Trotsky, and a wife who doesn’t wear a bra through the whole film.

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.

Funniest moment: When Davidson finally cracks, he cracks hard – his confession is equal parts triumphant, cathartic, and hilarious.

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.

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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.

Funniest moment: His straight-faced insistence at the door that they have a “wooden-duck situation”.

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.

Funniest moment: Both heart attacks are very funny, but the first (non-fatal) one just pips it for the sheer suddenness of it.

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.

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Funniest moment: Having escaped yet again, Doug Judy leaves Jake a pre-recorded message in a karaoke booth – complete with a full hour of pre-recorded singing for Jake to duet with.

The post Brooklyn Nine-Nine’s Funniest Guest Cast Characters appeared first on Den of Geek.

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vernonfielding · 4 years

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The lies, the secrets

Story No. 3 of my Season 7 Countdown Project! Also: I’m still taking prompts for future missing scene fics.

Summary: “My time undercover in the mafia was actually kind of lame. I mean, I wanted it to be badass, but I'm good at computers, so I mostly just helped them switch over from AOL.”

The story of how Jake became the mafia’s IT guy. Takes place during Undercover. (Read on AO3.)

What he doesn’t tell any of them, after he’s back, is that going undercover with the mafia is mostly just- really lonely.

Jake spends most of the first week alone in the crappy one-bedroom the FBI hooked him up with in Bushwick, waiting for one of the Ianuccis to get in touch. At night he lies awake on his mattress on the floor, mustard-yellow streetlight glaring through the grimy bedroom windows, and thinks that he’s already failed his assignment, that he couldn’t pass himself off as a disgraced cop for even one night. (The irony does not escape him.)

Then a guy calls Jake’s burner at 3 in the afternoon on the sixth day, and he introduces himself as Derek and says he’s downstairs. It’s now or never. Jakes takes a deep breath and blows it out hard, then steels himself and heads down. By the end of the week, he’s got a pierced ear and a gold-chain necklace and a cigar burn on the back of his neck, just below the collar of his new silk shirt. Years ago, before he’d gotten into the Academy, Jake had thought about getting a tattoo (“yippee ki yay” in calligraphy, very classy) in that spot and he’s grateful now that Gina talked him out of it. The burn was an initiation, and it didn’t hurt as much as he’d thought it would, but the scab is itchy and sometimes when he thinks of the smell of it he gets a little nauseated.

Leo Iannuci sends him out with Derek on a couple of jobs – mostly picking up cash from people they’re extorting from, but sometimes they’re the ones making the threats and Jake hates that part, hates it so much. Derek’s a nice guy, an Academy dropout who seems to shed his tough-guy attitude with his velour jacket every time they leave a bodega or laundromat or some other business where he’s had to smack someone around. Derek always does the hitting, never makes Jake do it, and Jake can’t decide if it’s because he likes the violence or if he just senses that Jake really, really doesn’t.

Either way, he’s grateful, and he has to keep himself from feeling too much fondness for Derek just because he protects Jake from the dirty work. Jake’s gotten that talk from the FBI: It’s natural to think you’re making friends, making connections, they’d said. But you’re not. Don’t ever forget that. Jake is always, always on his own.

About a month in, Jake is at Leo’s penthouse in Flushing, reeking of cologne that one of the Sals had doused him in while another Sal held him down, when Leo swears loudly and slaps the side of his computer, a rickety old desktop with a fan that sounds like it’s working triple-time.

“Motherfucker, it won’t let me fucking update!” Leo slams his fist down on top of the harddrive.

Jake looks around the room but everyone else suddenly seems to have important business on their phones, so he approaches Leo and says, “What’s the problem?”

Leo snarls at the computer. “I had to add some new clients to the ledger and now this son of a bitch won’t save the changes.”

Le’s “clients” could mean extortion victims or dirty cops or assassins-for-hire or any or all of the above. Jake hasn’t seen the ledger yet – he wasn’t actually sure there was one before this moment.

“You want some help?” he says, casually.

Leo finally turns his glare to Jake, staring him down long enough that Jake has to fight to keep from shifting on his feet and curling his hands into fists. “You any good with this shit?” Leo says.

Jake shrugs. “Yeah, I know computers.”

“All right, have at it,” Leo says, and gets up from the desk.

Jake sits, and Leo grips his shoulders, sudden and fast, fingers digging hard enough to bruise. And then just as suddenly he’s let go. He stays behind Jake, though, watching him click through open windows to find the source of the problem. It doesn’t take long.

“You’re using AOL,” Jake says. His voice sounds a little strangled to his own ears.

“Yeah, I guess,�� Leo says. “So what?”

“So that’s your problem,” Jake says.

Jake’s definitely not an expert at computers, but he’s always had an affinity for the basics and it only takes him a few minutes to fix the immediate problem – an outdated file type that the desktop won’t recognize anymore. Jake saves the document, which, infuriatingly, is a table someone made in Microsoft Works. It’s so horrifically formatted that Jake can’t help but imagine the devastating stroke that Amy would suffer if she even knew it existed. She would seriously start bleeding out of her eyes.

Later that night, Jake smokes his first full cigar and convinces Leo to let him move all of their documents to a Google drive. By the end of his first full month undercover, Jake’s become the mob’s IT guy. It’s exactly as dope as it sounds. (It’s not remotely dope.)

+++

It takes him a couple of weeks to transfer everything to the cloud; he has to carefully rebuild all of the ledgers in proper spreadsheets. Leo assigns one of the Sals to keep an eye on him, but after the first hour Sal gets bored and retires to the couch to play Kwazy Cupcakes on his phone (the sound effects touch off a profound homesickness that Jake tries his best to ignore). So Jake has no trouble copying the ledgers onto a thumb drive that he later passes on to his handler. It’s almost all the evidence they need. Then it’s just a matter of waiting for the FBI to get its teams in place, to mark the right time and place to take down the biggest targets.

Jake does a few more jobs with Derek, and he just misses getting sent on a drug run that ends in a shootout and two of Iannuci’s guys in the hospital (Jake was back at Leo’s penthouse trying to figure out why his computer suddenly refused to talk to his printer). He knows he’s dodging literal bullets, but that doesn’t mean he sleeps well at night, or that his nervous system doesn’t light up like a Christmas tree every time someone racks a gun near him (which is pretty much all the time – mafia guys love cleaning their weapons).

Jake ends up giving a seminar to half a dozen Iannuci men (plus two women) on file encryption and two-step authentication and he feels a little guilty for teaching the mob how to evade hackers – some of whom will surely be cops – but weirdly, he’s starting to get bored, and he figures none of them are going to remember any of his lessons anyway.

The night before Marco and Angie’s wedding, Jake gets super drunk with a bunch of the guys and he sings “The Longest Time” with Derek, slopping rye whiskey all over their polyester shirts. The next day Jake’s going home. But that night, for the first time in 62 days, he forgets to be lonely.

End Notes:

Title is from Feed the Beast (Bash Brothers).

I know there is a lot of mafia-Jake fic, and that this take is not like the others. But I always thought Jake’s comment to Pimento about what he really did undercover was interesting and worth exploring. I don’t think it means the job wasn’t dangerous or super stressful for Jake, though my version is probably less so than some of the more violent takes some writers have offered (which are just as valid!).

I couldn’t decide if this story should be considered a missing scene for Undercover or Adrian Pimento. It fit better here for obvious reasons, but the revelation is in the later episode. But really, it doesn’t actually matter.

My darling beta @fezzle wisely pointed out that Jake the Computer Wizard doesn’t exactly fit with what we learn about him in Ticking Clocks. My solution/answer to this is that Jake is actually pretty good with day-to-day computer stuff (there’s quite a bit of evidence of this in canon – or at least, evidence that he’s not BAD with computers), but hacking-level stuff is way over his head. That’s why he starts Ticking Clocks full of bluster with the so-called security expert and then eventually has to admit he doesn’t know what he’s talking about. Unfortunately, what he actually says is “I don’t know anything about computers.” That could be the writers just forgetting their own canon, but I choose to believe that it actually fits just fine with Jake’s “I’m good at computers” in Adrian Pimento. It’s all about context!

#b99 fic #b99 season 7 countdown project #missing scene #undercover #jake peralta #mafia jake

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