Outshining other sitcoms of its time, Brooklyn Nine-Nine quickly rose to the top of the charts and became a viewers’ favorite. With its unique combination of comedy, sentimentality, adorable character relationships, and representation of real-world issues, the show captured the hearts of audiences far and wide.
Regardless of all its heartwarming traits, Brooklyn Nine-Nine was a cop show, loaded with dangerous situations and risks. The show featured countless criminals, from murderers to petty thieves, but some of these played substantial roles that made the best storylines.
The spoiled son of Deputy Commissioner Podolski (James M. Connor), Trevor Podolski (Michael Grant), was arrested by Detective Jake Peralta (Andy Samberg) after he was caught vandalizing police cars by drawing penises on them. Jake takes him back to the office to file an official report before realizing his relation to the deputy commissioner. When he finds out that Jake has arrested his son, Podolski turns up at the office and uses his superior status to let Jake go of his son.
Later, after a talk with Captain Raymond Holt (Andre Braugher), Jake decides to arrest Trevor for a second time, putting his duty over his fear of Podolski. Though merely a criminal, Trevor’s arrest is a development in Peralta’s approach to his job, marking an achievement after the new captain’s arrival.
Debbie Fogle (Vanessa Bayer) was the NYPD officer paired with Capt. Raymond Holt when he was on patrol duty, as ordered by new acting commissioner Madeline Wuntch (Kyra Sedgwick). A sweet and innocent character, Debbie seems to blend in the background, outshone by the detectives at the ninety-ninth precinct. Her isolation from the group serves as a perfect circumstance for her to do anything without being noticed.
Using the opportunity to her advantage, Debbie steals cocaine and weapons from the evidence lock-up but gets easily caught because of her naïveté.
The first-ever perp arrested in the series, Ratko (Nick Gracer), was the villain of the pilot episode. He was a Serbian criminal who worked as a butcher at Beneficio’s Gourmet Market. The cops were investigating the murder of Henry Morgenthau, a luxury food importer who was killed in his apartment.
An intelligent observation by Boyle (Joe Lo Truglio) leads Jake to interrogate Ratko, who escapes the scene. Jake decides to pursue him and catches him in a raid on the storage unit in Boerum Hill he frequents.
Eleanor Horstweil (formerly Boyle) is Charles Boyle’s ex-wife, who bullies him throughout their marriage and long after their divorce. She also forced him to rent out her basement when she divorced him and got re-married, which was genuinely heartbreaking.
While Charles has a bit of generally lousy luck with women until Genevieve (Mary Lynn Rajskub), Eleanor (Kathryn Hahn) is the worst. When Charles moves in with Genevieve, he decides to unfreeze the sperm he saved before he got a vasectomy as per Eleanor’s wish. Eleanor tries to blackmail Charles under a contract they made, but Jake ultimately makes him realize that Charles will be a great father to any child, biological or not.
Caleb John Gosche
Caleb John Gosche (Tim Meadows) is Jake Peralta’s cellmate during his time at the Jericho Supermax Prison over two episodes of Season 5 of Brooklyn Nine-Nine. He’s serving three life sentences for cannibalism and has already spent over 15 years in jail.
He is also featured in season 6 when Jake is looking for a serial killer who’d been murdering young men and carving out their hearts. While he’s a little scary and has an unsettling sense of humor, Caleb is a great friend to Jake and supports him through his time in prison. He is also one of the most interesting criminals on the show.
Ernest Zumowski (Kevin McDonald), aka the Disco Strangler, was an unhinged murderer who used yo-yo strings to murder his victims. He is Captain Raymond Holt’s arch-nemesis and, as part of an elaborate prison break, faked his own death. Captain Holt is immediately suspicious, even though said criminal is over 80 years old, and the medical examiner confirms his body DNA matches that of Ernest.
His suspicions are proved correct when a camera reveals that the strangler faked his death and fled through the woods. He leads a team through the city, leading to a (not so) epic showdown between Holt and “the most dangerous man in America,” now a crippled octogenarian who weighs just 93 pounds.
Commissioner of the New York Police Department, John Kelly (Phil Reeves), planned to implement a “vigilant policing initiative,” which was just a cover for the “stop-and-frisk.” He got the job over Capt Raymond Holt when he contested for elections, and when the captain opposed his cruel policies, he made it his life’s mission to make things difficult for his precinct. He introduces an app to allow the public to send in anonymous tips, which is a cover-up of the illegal use of a Stingray Phone Tracker to spy on civilians.
The Nine-Nine, together with the Suicide Squad: Vulture (Dean Winters), CJ (Ken Marino), and Madeline Wuntch – expose him, and he is fired. Though, later in the show, Madeline Wuntch – the new acting commissioner tells Holt that Kelly had secured a “higher-paying job in the private sector.”
The notorious head of the most brutal crime family in New York City, Seamus Murphy (Paul Adelstein), is a gangster who manages to manipulate the squad at the ninety-ninth precinct at a particularly vulnerable time. He convinces Amy (Melissa Fumero) to make a deal with him that could save Jake from legal troubles in exchange for a favor, but Capt. Holt convinces her to turn Seamus down. Later, Holt takes the deal himself, owing Seamus.
When Seamus tries to use his favor to support a crime, the squad outwits him, and he threatens to murder Kevin Cozner (Marc Evan Jackson), Holt’s husband, which leads to Kevin being hidden in a safe house and the team working overtime to protect him.
A lieutenant with the NYPD, Melanie Hawkins (Gina Gershon) runs a special task force on bank robberies that have been happening for over three months. Jake and Rosa (Stephanie Beatriz) are beyond thrilled to join her team. All of their excitement goes down the drain when it is revealed that she is a dirty cop and her squad comprises the Golden Gang bank robbers.
In a move to save herself, Melanie frames Jake and Rosa for the robberies. Eventually, she is proved guilty and arrested, but her time at Brooklyn Nine-Nine marks one of the best storylines on the show.
Douglas “Doug” Judy (Craig Robinson), aka the Pontiac Bandit, is a thief and con artist renowned for stealing over 200 Pontiacs. He is the arch-nemesis of Detective Jake Peralta, who he conned the first time as an informant to lead him to Pontiac Bandit. However, they both share an immature and laid-back attitude that bonds them together. Despite the numerous times that Jake has tried to arrest him, Doug has found his way out of Jake’s grasp and has run for the hills.
In the finale of Brooklyn Nine-Nine, Jake arranges a special goodbye for Doug and gives him a second chance at life. They refer to their friendship as PB&J: Pontiac Bandit and Jake, after the widely loved Peanut Butter and Jelly sandwich.
NEXT: ‘Brooklyn Nine-Nine’ Cast and Characters (And What They’re Doing Now)