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When Brooklyn Nine-Nine introduced its first Halloween heist, fans knew they were in for something unique. Each Halloween, Detective Jake Peralta (Andy Samberg) and the rest of the 99th Precinct crew would up the ante with a hilariously chaotic heist. By the time we reached Halloween, the fifth installment of these episodes, the tradition had become a cornerstone of the series—a chance for the characters to try out-cunning each other in a dizzying race to snag a “cummerbund” or “belt” and claim the title of “Ultimate Detective Slash Genius.”
Halloween, the fourth episode of season five, locked the heist into Brooklyn Nine-Nine history. Taking place entirely within the precinct, it captured the 99’s escalating rivalry, with betrayal, handcuffs, and a clever corgi named Cheddar. Things started when Jake and Boyle (Joe Lo Truglio) shut off the lights and launched into a scheme involving ceiling tiles and hidden stashes. Before long, Boyle double-crossed Jake, Captain Holt (Andre Braugher) swooped in with a stationary bike-powered corgi lift, and Amy (Melissa Fumero) swapped out Cheddar with a decoy. Sound complicated? Well, it was, but in the best way possible.
Halloween had fans grinning from ear to ear through all the ridiculousness, and it wasn’t just because of the clever twists. Halfway through the heist, Jake turns the game on its head by staging the whole event to propose to Amy. The reveal was a masterstroke, using the Halloween tradition to surprise Amy and the audience. After years of working together and constant one-upmanship, Jake’s proposal felt like the ultimate win, proving he could still catch her off guard. He even staged the moment in the precinct’s evidence room—where they shared their first kiss.
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