Jake And Amy’s Best Moments On Brooklyn Nine-Nine, Ranked

Probably the best-known and most beloved running gag on “Brooklyn Nine-Nine,” the Halloween Heist gets progressively more outrageous every season. First Jake wins, followed by Holt in Season 2, then Amy sneaks around and steals the whole thing in Season 3, opening up the field for every member of the Nine-Nine. After Gina’s non-detective win in Season 4, Amy, Holt, and Jake are all dead-set on winning Season 5’s Heist in “HalloVeen,” in which they must be in possession of a wrestler’s championship belt.

The episode takes the usual twists and turns, with characters betraying each other left and right while Amy, Jake, and Holt bring new meaning to the word suspicious. Amy and Jake find themselves alone in the file room with the belt, and Amy is about to declare herself successful when Jake tells her to look at the belt a little more closely. 

When she’s finished reading “Amy Santiago, will you marry me?” she finds Jake on one knee, holding out a ring to propose to her. It was actually a surprise, which is hard to do with an episode set-up that’s already been run on the show four times prior, and Jake’s decision to propose to Amy with the heist is a beautiful testament to the playfulness that they bring out in each other.