1. HalloVeen (Season 5) – This is the first year where it is every man for himself as the squad fight for the “Amazing Human/Genius” belt, or as Captain Holt (Andre Braugher) insists the “Amazing Human/Genius” cummerbund. In an unexpected but touching twist to the show, Jake (Andy Samberg) uses the heist to propose to Amy (Melissa Fumero) when she least expects it. Another highlight includes Jake distracting the squad by dressing up as handmaids from The Handmaid’s Tale.
2. Halloween Part III (Season 3) – The first heist in which Jake and Amy are officially a couple, this leads the whole squad to distrust Amy and leave her out of the heist to win the crown. However, things get out of control as an unknown third party steals the crown from Jake and Captain Holt. Out of revenge, Amy plots against everyone as Al the janitor and is crowned the Queen of the 99 and “Amazing Detective/Genius”.
3. Halloween (Season 1) – The one that started it all. Initially a bet between Jake and Captain Holt, Jake gets the whole squad involved to defeat Holt and steal his prized medal of valour. Boyle (Joe Lo Truglio) tries to bond with Amy by convincing her Halloween is fun. Highlights of the episode include Jake stuffing pigeons into Captain Holt’s air vent and a synchronised dance sequence by suspects dressed as royal babies. Jake succeeds and is declared the first “Ultimate Detective/Genius”.
4. Halloween II (Season 2) – The origin of the infamous “Halloweeeeeeen” quote, Jake attempts to steal Captain Holt’s watch from his wrist. Gina (Chelsea Peretti) is danced out of her dance group “Floorgasm” and Terry (Terry Crews) offers to dance with her at the competition. Holt gets his revenge on Jake, revealing he planned the heist the year before with the rest of the squad to conspire against Jake. With the heist scores being 1-1, Holt wins the title of “Ultimate Detective/Genius”. Highlights include Gina and Terry dancing to Salt ‘n’ Peppa as Mr and Mrs Terry Jeffords.
5. Halloween IV (Season 4) – As the squad pair off to win the “Ultimate Detective/Genius” plaque from Amy’s childhood caboodle, the gang suspects Terry is conspiring against them solo. Amy and Rosa (Stephanie Beatriz) put aside their differences and team up, with Rosa even using Amy’s codenames taken from The Babysitters Club. Jake enlists the help of Boyle’s creepy doppelganger Bill to trick the others, as Holt uses Boyle to make Jake helpless. In a twist not dissimilar from Season 3, Gina is the shock conspirator despite initially being paired with Jake. By stealing the plaque, Gina requests for the title of “Ultimate Detective/Genius” to be changed to “Ultimate Human/Genius” so that she is no longer discriminated against as a secretary. Although a good and funny episode, this heist is not as memorable as past Halloweens.
Special shoutout for Season 6's Cinco de Mayo for not making the list; although the most recent Halloween Heist episode, it doesn't meet the same standards that fans have became accustomed to.