Throughout its eight seasons, Brooklyn Nine-Nine has perfected its classic structure. In a typical episode of Brooklyn Nine-Nine, Jake Peralta (Andy Samberg) creates chaos and challenges authority with his unconventional methods, yet he usually ends up correctly solving a case or executing another clever plan. Complementing these episodes is the show’s fantastic ensemble of characters, who often either assist Jake or clash with him over the case of the week.

There are many excellent episodes of Brooklyn Nine-Nine that utilize its tried-and-true structure, including “HalloVeen” and “The Fugitive.” However, Brooklyn Nine-Nine‘s best episode is one that completely breaks this structure. Season 5, Episode 14, “The Box,” is a bottle episode that takes place almost entirely in an interrogation room with only Jake, Captain Holt (Andre Braugher), and their prime suspect in a murder case – a successful dentist named Dr. Philip Davidson (Sterling K. Brown). “The Box” stands out as a true masterpiece due to its unique approach.

‘Brooklyn Nine-Nine’s “The Box” Is a Bottle Episode With Heightened Stakes

Brooklyn Nine-Nine‘s “The Box” begins with Jake greeting Captain Holt, who is preparing to leave for the night to attend the opera with Kevin (Marc Evan Jackson). Jake outlines the situation: a dentist named Robert Tupper has been murdered, and his business partner, Philip Davidson, appears very guilty but has a weak alibi. Without real evidence against Philip, they must extract a confession from him now or he may never be convicted. Holt cancels his opera plans to assist Jake with the interrogation, which mainly consists of them questioning Philip. They attempt various techniques, such as “smart cop / dumb cop” and Jake’s iconic scream-singing, but Philip remains calm under pressure, leaving them at an impasse. Ultimately, while alone with Philip, Jake manages to get him to admit knowledge of where Robert’s body was discovered.

However, this admission alone isn’t enough for a conviction. Jake decides to deceive Philip by claiming he was seen at the crime scene. This marks the beginning of escalating tension between Jake and Holt. Jake aims to prove to Holt that he can handle this alone, while Holt tries to prevent Jake from overstepping his bounds. Philip senses the growing conflict between them and exploits it. He suggests that Holt doesn’t trust Jake’s abilities as a detective, which provokes Jake’s anger and leads him to stray from their planned approach in an attempt to secure a confession.

As time runs out and it seems they will fail to get Philip to confess, Jake shifts strategies with only eight minutes remaining before they must release him. He accuses Philip of murder by reconstructing what he believes happened step by step. Misleadingly identifying the murder weapon as being used spontaneously allows him to imply that Philip was fortunate not to be caught. Finally, frustrated by being underestimated, Philip reveals a detailed confession. Holt then expresses his admiration for Jake’s skills as they realize it’s already time for work the next morning.

‘Brooklyn Nine-Nine’s “The Box” Uses the Limitations of Its Structure to Heighten the Tension

“The Box” is Brooklyn Nine-Nine‘s best episode for two primary reasons: it features an intriguing central murder plotline and its structure brings the unspoken emotional conflict between Jake and Holt into focus. Although both believe throughout that Philip is guilty, there remains a possibility of an unexpected twist revealing his innocence. Brown’s performance perfectly conveys this tension as Philip remains calm and composed while often making Jake and Holt appear unreasonable. This is why Philip’s eventual confession is both shocking and makes complete sense for his character. It culminates in an intense moment where Jake elicits from Philip the details of his meticulously planned murder, including how he melted down the murder weapon for use in dental care.

“The Box” could have served as a lighthearted departure episode, but what elevates it is how Brooklyn Nine-Nine employs the bottle episode format to explore underlying issues in Jake and Holt’s relationship. By Season 5 of Brooklyn Nine-Nine, their bond has deepened significantly, with Jake viewing Holt as a father figure. This connection explains why Jake is so concerned about Holt’s opinion of him and why he feels insecure when he perceives doubt from Holt regarding his detective skills. Holt chooses to skip the opera for this interrogation because he values this aspect of their work together, yet Jake misinterprets it as a lack of trust in his abilities. The two clash throughout the episode as they each believe their approach will succeed with Philip. Ultimately, for Jake to secure a confession from Philip, he must set aside his ego and confront Philip directly. This resolution beautifully intertwines both physical and emotional arcs within the episode as Philip confesses and Holt acknowledges Jake’s success with an enthusiastic “Oh damn.”