Brooklyn 99’s heist episodes should all be watched, but here’s the best of the best in the series historic run.
By Jonathan Klotz | Published
One of the best parts of Brooklyn 99, along with the fun recurring characters, is the yearly tradition of a heist episode for Halloween. From the first one that set the standard to the very last eight seasons later, the annual heist kept audiences guessing while constantly raising the bar. Every one of these episodes is among the best in the series, which makes this a list of nothing but winners, though, as the heists taught us, not all winners are equal.
8. Halloween 4 – Season 4, Episode 5
By Season 4, the entire cast of Brooklyn 99 takes part in the annual Halloween heist. Starting off with competing announcements from the previous three winners, it’s to determine who is “The Ultimate Detective/Genius,” by stealing a plaque locked in a “ca-boo-dale” after all photos of Al Gore have been removed. Fairly straightforward until the ending twist (which becomes a series staple), the appeal of this one is in the character pairings.
Jake (Andy Samberg) and Gina (Chelsea Peretti), Amy (Melissa Fumero) and Diaz (Stephanie Beatriz), and Holt (Andre Braugher) with Boyle (Joe Lo Truglio), though these pairings have happened before, they’re among the best possible. What makes it the worst is that, well, not much happens, there are no really great lines, and the best moment is likely the involvement of Cheddar (or the recurring character of Bill, Boyle’s look-a-like). It’s still a fun episode, but it’s the weakest of the group.
7. Cinco De Mayo – Season 6, Episode 16
“Cinco De Mayo” may be set on the Mexican holiday, but it’s still a heist episode, the Brooklyn 99 writers had to get creative six years into the show’s run. In-universe, it was explained by a gas leak, which Jake and Holt assume is fake, and then everyone coming together to stage a heist to distract Terry (Terry Crews) from his upcoming lieutenant exam.
Though it’s still a funny episode, it’s one of Brooklyn 99’s weakest heists, despite including the usual betrayals, sudden twists, and Cheddar. After years of not being heavily involved in a heist, it’s great watching Terry take center stage.
6. Halloween 2 – Season 2, Episode 4
Still early in the run of Brooklyn 99, “Halloween 2” was fleshing out the characters, and as a result, it’s fairly grounded compared to the later seasons. This time around, the heist target is Holt’s watch, and Jake enlists the entire squad to help him get it, but unlike the first time out, everything goes wrong almost from the start.
There are twists and turns as Jake descends further into madness, and in what becomes a staple of the heist, there’s multiple layers of deception. A recurring Brooklyn 99 bit debuted here as well, with the introduction of Gina’s (Chelsea Perretti) dance team. Also, one of the best Jake lines of the season, “You can’t wash a car,” explains so much about where he started as a character.
5. Valloweaster – Season 7, Episode 11
Brooklyn 99 took the Cinco de Mayo heist concept to the next level by spreading out Season 7’s heist over three holidays, Halloween, Valentine’s Day, and Easter. The heist this year, to grab Thanos’ gems (cheap knock-offs since the actual merchandise was super expensive), gets sidetracked twice, once by Cheddar eating them and then again by Sully…also by eating the gems.
This year, the squad is paired off and handcuffed to their partner, with Rosa ending up handcuffed to a filing cabinet since that’s the closest they could find to Scully’s capabilities. Becoming a full-on cartoon this year, it’s the most over-the-top heist yet and ends with someone jumping off the roof of the building.
4. Halloween Part 3 – Season 3, Episode 5
“Halloween Part 3” opened up the heist for everyone else, setting the template that Brooklyn 99 would follow in all of the following years. In the process, the audience is introduced to Heist Amy, the dangerously competitive side of the usually by-the-book Amy, that is accused of working with both Jake and Holt at different points.
Despite Terry’s family getting involved and Holt navigating the outside of the building to sneak in, neither Jake nor Holt end up with the prize this year. The ending twist is one of the best, and unlike most of the others, Scully gets to be involved. Sort of.
3. HalloVeen – Season 5, Episode 4
“HalloVeen” is one of the best episodes of Brooklyn 99; not only is it a wild step up from the fairly tame previous year, but the twist this time is the emotional payoff to Jake and Amy’s relationship. The usual gags are present, from a horde of Handsmaid’s Tale cosplayers to Cheddar, though this time there are multiple Cheddar’s, and this year, a new gag starts up, as everyone argues who has the most heist victories.
Filled with Jake’s usual references and a lot of asides about “that’s how you’re defining our relationship,” “HalloVeen” hits all the right beats for a Brooklyn 99 heist. Everyone turns on the romantic gesture at the end out of frustration that Jake hijacked the annual event, which is the perfect reaction to what on any other show would be a celebration.
2. Halloween – Season 1, Episode 5
“Halloween” aired on the air during Brooklyn 99’s second month, long before the audience realized they were watching a live-action cartoon. That’s part of what makes the very first heist one of the best: no one knew what to expect. Jake’s wager with Holt to do all of the squad’s paperwork for the night manages to unite the department against their captain, but it’s the details that made it exceptional.
The final declaration that Jake is the “Ultimate Detective/Genius” comes back every single year, and while the heist for Holt’s Medal of Valor is quaint by the time “HalloVeen” rolls around, it’s still a masterclass of a sitcom episode.
1. The Last Day – Season 8, Episode 9
“The Last Day” is a two-part series finale, making it the final heist for the team at Brooklyn 99 and a fantastic send-off for the show. It’s also an in-universe good-bye, with Jake and Amy using the heist to stage Jake’s good-bye to the squad.
Filled with emotional moments and playing off of not only the prior heists but all of the character growth that took place over the last eight years, “The Last Day” is also one of the best series finales ever to air. All that, and there’s another first-time winner this time, and it’s the last character anyone would have expected, leaving only two members of the squad without a win.