Brooklyn 99 has an incredibly long list of recurring guest stars (Doug Judy, The Vulture, several relatives of the precinct members) but the one who is easily the most eccentric is Adrian Pimento, a delusional former-detective who spent twelve years undercover working for a notorious crime-lord.
Few characters could make such an impressionable footprint on a television series (especially when said character only has ten appearances on a show that has over 140 episodes) but that's the beauty of Adrian Pimento. The crazy, yet enlightened, man quickly made a spot for himself in the 99, as well as in fans' hearts.
Kicks, Season 5 Episode 3
Despite being a fan favorite and having a multiple year engagement to one of the series main characters, the writers did Pimento dirty by virtually writing him out of the series in the fifth season after Jake and Rosa returned from prison. The episode's B story revolved around Rosa following Pimento (who was acting crazier than usual) and she caught him cheating with another woman. Later on in the episode, Adrian reveals that the woman Rosa caught him with was actually his Spanish tutor and he was learning it for her. The kind-hearted gesture was met with sex, then a spontaneous break-up from Rosa despite his non-cheating. Pimento deserved better than this.
Cheddar, Season 3 Episode 18
It's hard to believe that it was only in Pimento's second episode that he and Rosa sparked the relationship that would last until Season 5. In fact, their spark is so hot that a convicted pervert asks if they can cool it. Meanwhile, Captain Holt goes to Paris to visit Kevin and he leaves Jake and Amy in charge of his house. Unfortunately, the duo accidentally let Holt's dog, Cheddar, get loose and Pimento and Rosa help look for him by putting up flyers. Rosa eventually asks Pimento if they're ever going to hook up and Pimento runs away frightened, only to come back later after a talk with Terry whereupon he asks Rosa to marry him. She declines, but they do start dating.
Terry Kitties, Season 3 Episode 19
While Jake and Terry try to solve a case that Terry botched two decades earlier, the B story of the episode follows a homeless Pimento sleeping on the precinct's break couch. Boyle offers to help Adrian if he can and Pimento takes it as an invitation to move into Charles' apartment.
After several disturbing/sleep-deprived nights pass, Charles admits to Gina that he can't take living with Pimento anymore but he also can't bring himself to ask him to leave. This prompts Gina to step into her role as the Alpha of the office and force Adrian to move out of Boyle's apartment.
The Bank Job, Season 4 Episode 21
This was no doubt a hilarious appearance, but it was so brief and random that it really had fans scratching their heads. Pimento had returned from hiding in the beginning of season 4 when Figgis was finally captured, but for some reason he never returned in season 4 after episode 7... that is, until episode 21, when Pimento shows up for a few short scenes where he helps Rosa and Jake take down a dirty cop. Pimento's appearance includes threatening to kill children with a foot-long knife, getting the crap beaten out of him by Jake, and snorting enough cocaine to kill a grizzly bear. Hilarious, but so random.
Mr. Santiago, Season 4 Episode 7
During the Thanksgiving episode of season 4, the entire precinct gets invited to spend the holiday at Amy's apartment due to the fact that her Dad is coming to meet Jake for the first time. While Jake and Mr. Santiago try to solve one of his twenty-year-old cases, Pimento takes a $2000 check given to him by Holt in order to become a P.I. and bets it all on one of the dogs from the National Dog Show.
Holt forces Adrian to try and get the money back, but it's too late - however, it turns into their lucky day as the dog Adrian bet on wins the entire show.
Paranoia, Season 3 Episode 20
Pimento's final appearance in season 3 was one of the most memorable episodes of the series. Not only does the episode start off with a crazy-twist as Pimento and Rosa end up getting engaged after dating for less than two episodes, but the episode quickly takes an even wilder turn when Pimento reveals to the guys at his bachelor party that somebody has been following him and is trying to kill him! Terry doesn't buy it (due to Pimento's insanity) until they actually catch the contract-killer hired to assassinate Pimento. It's revealed that the man who hired the contract-killer not only works for Figgis (the man who Pimento spied on for 12 years) but also is a double-agent at the FBI. The heat cause Pimento to call off the wedding and disappear.
Monster in the Closet, Season 4 Episode 6
Poor Nikolaj. When the 99 catches Figgis in Florida in the beginning of season 4 it allows Pimento to come out of hiding and return to the precinct. When he arrives, he and Rosa pick up right where they left off when he had to disappear and they decide to get married. However, all throughout the episode Pimento and Rosa seem to do everything they can to sabotage the wedding and end up calling off the wedding for a second time. That said, they don't break up and just decide to date for longer than two episodes before getting hitched.
Gray Star Mutual, Season 5 Episode 18
Another hilarious episode that was as confusing as it was funny. As already stated, Pimento was essentially written out of the show in the third episode of the 5th season - that's why fans were so confused when Pimento showed up for a single appearance only 15 episodes later. Not only that, but Pimento was now somehow an insurance appraiser?
Despite the oddness, the episode was comedic as they come as it followed Pimento denying Charles' claim when his food-truck burns down. The episode turns emotional when Jake reveals that Pimento wasn't invited to his and Amy's wedding, but everybody effectively makes up in the end when they help solve the case of who burnt down Charles' truck.
Pimemento, Season 7 Episode 3
Without a single appearance in all of season 6, this episode was long time coming. While Pimento might not have a decided annual episode (like Doug Judy) fans thoroughly enjoy seeing the shaggy-haired maniac and they were rewarded in season 7 with a surprise appearance. The episode spoof's on Christopher Nolan's movie Memento when Adrian shows up at the 99 with amnesia and can't remember who/where he is. Jake and Charles help Pimento solve the case of his missing memory (which turns out to be Pimento's doctor giving him mind-wiping drugs) and ends without answering where Pimento had been all season 6 or where he'd be going.
Adrian Pimento, Season 3 Episode 17
Could it have been any other episode? The introduction of Adrian Pimento in season 3 was one of the best additions that Brooklyn 99 has made in the entirety of the show. Jake spots an odd-looking stranger at his desk, only to get a knife held to his throat simply for touching the man's shoulder. The man is revealed to be (dun, duh-duh-duh!) Adrian Pimento, a former detective who had returned from 12 years of undercover work. Due to his PTSD from being undercover for so long, Adrian immediately freaks everybody out with his weird vibes and crazy mannerisms and it causes him to consider leaving the force. Fortunately, Jake talks him out of quitting and the character of Pimento became much more than a one-and-done guest star.