Brooklyn Nine-Nine has created a number of unforgettable recurring characters: flinty Madeline Wuntch (Kyra Sedgwick); antic Adrian Pimento (Jason Mantzoukas); stoic Kevin Cozner (Marc Evan Jackson); the ruthless Vulture (Dean Winters), but none is as beloved as the one whose annual return is always accorded its own episode: Craig Robinson's Doug Judy.
Lore has accreted to Doug since his introduction in the show's first season, in episodes characterized by the kinds of twists and reversals you'd expect of a career con artist. Doug's Season 7 visit Thursday night had us thinking about the Doug Judy canon. Which outing worked the best? Which was the least memorable? With this in mind, we've created the definitive ranking of all Doug Judy's Brooklyn Nine-Nine appearances to date. (Warning: spoilers ahead.)
7. Season 5 - Episode 13: "The Negotiation"
When a B&E goes awry at a jewelry store, Jake (Andy Samberg) is thrilled to learn the hostage taker has personally asked that he act as negotiator... until he arrives on the scene and sees that the perp is Doug Judy, who Jake thought had gone straight! Doug promises that he has, but says a crime boss named Martin Halliway is forcing him to do one last job to compensate him for a costly double-cross from Doug's former life of crime. Halliway has threatened to harm Doug's beloved mother if he does not cooperate. Not only are we denied a trademark musical break marking a Jake/Doug costume change (in this instance, changing into beat cop uniforms in order to escape the jewelry store); but the supposed crime boss Halliway is such a non-entity that he gets no lines, and Mrs. Judy remains off-camera! Ripoff.
6. Season 4 - Episodes 11 & 12: "The Fugitive, Part 1 & 2"
Nine incarcerated men escape from a transport accident, and it falls to the officers of the Nine-Nine to apprehend them. In the first half of this two-parter, Amy (Melissa Fumero) and Jake — partnered with Charles (Joe Lo Truglio) and Terry (Terry Crews), respectively — compete to bring in the most cons, with the winner forcing the loser to move in with him or her, until Jake resigns at the end, giving up his apartment despite such features as black mold and one gray towel that (a) was there when he moved in, and (b) never entirely dries. Eventually, just one prisoner remains: George (Charles Baker), a former foster brother to Doug Judy. To secure Doug's co-operation in apprehending George, Captain Holt (Andre Braugher) very reluctantly agrees to grant him immunity on his 600 outstanding charges, but since he continues to doubt Jake's objectivity, he joins the sting himself, and Undercover Holt is always fun. This one also benefits from a delightful B-plot involving Amy and Gina (Chelsea Peretti) agreeing to add Charles back on one of the squad's many text chains only if he passes their remedial course in texting etiquette — something that, as the buyer of multiple Property Brothers emoji apps, he definitely needs.
5. Season 7 - Episode 08: "The Takeback"
Diaz (Stephanie Beatriz) has the unfortunate duty of informing Jake that her latest collar had a compelling piece of evidence in his vehicle: an invitation to Doug Judy's wedding! Jake meets up with Doug at a pottery-painting place to confront him about why he wasn't invited, getting hooked up for Doug's bachelor party instead — as long as Jake attends under an alias and with a criminal backstory, since Doug's friends think it's weird that he's a cop. All is well until another guest, Doug's sister Trudy Judy (Nicole Byer), outs Jake, though she later covers in exchange for a promise of seeing 14 butts. It's a good thing Jake's not a cop, Doug's buddies tell him, because they just stole some diamonds from the Russian oligarch staying in their hotel's penthouse! A reverse heist ensues, but as is so often the case, this Doug Judy caper is not quite what it seems. Truly a must-see for the latest in Judy entrepreneurship: who doesn't need a Smoosh Shoosh and who really cares if it suffocated Barbara Corcoran?!
4. Season 2 - Episode 10: "The Pontiac Bandit Returns"
Jake is super-psyched to apprehend Doug for the second time, until Doug announces that he plans to skate by snitching: he has information about a new drug called Gigglepig, on which Diaz has been running a task force for weeks. This is one of the more convoluted crime plots of all the Judy-sodes — I appreciate the fact that the show's producers put in the effort; I just don't think we always need every outing to be Ocean's Eleven. Still, it's ranked this high for the scenes among Jake, Doug, and Diaz in the Doug-negotiated four-star hotel room ("Robes!")
3. Season 1 - Episode 12: "Pontiac Bandit"
Diaz is eager to book a certain Doug Judy on the identity theft charges for which she's been pursuing him for a month. But he also has information on the Pontiac Bandit, whom Jake has been chasing for years, and he's so sure Doug's for real that he wagers 1,000 pushups — a bet he and Diaz established back in the police academy that the other couldn't contradict. Spoiler: all the information Doug feeds him about this prolific car thief — that he's a sharp-dressed Asian man with a British accent — is inaccurate, but it takes almost the entire episode for Jake to figure out that the Pontiac Bandit is Doug himself. The B-plot, in which Charles returns from having been shot, wildly embarrassing himself as the rest of the squad refrains from roasting him since he was injured in the line of duty, is a true all-timer.
2. Season 6 - Episode 05: "A Tale Of Two Bandits"
Jake has just been enlisted to sing at Doug's funeral by Doug's sister Judy. Then he sees Doug himself pop up at the back of the hall, because he faked his death to protect himself. Another underworld figure, Stefano Lucas, just had his car stolen by someone using Doug's old MO, so he put out a hit on Doug. On the way to the reveal of the car thief's actual identity, we get a couple of dreadlock wigs, a Widows homage, some very funny rhyming, and a bravura performance by Nicole Byer in her first appearance.
1. Season 3 - Episode 13: "The Cruise"
Jake has no suspicions about winning free tickets for a cruise — which will be his first real vacation with Amy— without having entered a contest. But she's going to have to set aside her extremely rigid schedule of activities, because the tickets did actually come from somewhere: specifically, from Doug Judy, Carousel Cruises' Entertainer of the Year, who invited them on board because someone's trying to kill him. Amy has to tell Jake he can't actually arrest Doug in international waters, and although the captain (Paul F. Tompkins) can, he doesn't care to, as around half the crew are criminals, including the tax-evading captain himself. Jake and Amy help Doug with his issue, but since Doug's face turn is yet to come, he evades justice himself, again. A spectacular B-plot finds Captain Holt receiving a visit from his sister Debbie, and while Terry and Gina are dubious about his claims that she's extremely dramatic— Terry: "One time I used an exclamation point in an email; you called me Diana Ross"— she is played by Niecy Nash and she more than lives up to Holt's description.
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Writer, editor, and snack enthusiast Tara Ariano is the co-founder of Television Without Pity and Fametracker (RIP). She co-hosts the podcasts Extra Hot Great and Again With This (a compulsively detailed episode-by-episode breakdown of Beverly Hills, 90210), and has contributed to New York, the New York Times magazine, Vulture, Decider, Salon, and Slate, among many others. She lives in Austin.