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Ranking the “Brooklyn Nine-Nine” Halloween Heist Episodes

“Brooklyn Nine-Nine” is, in my opinion, one of the greatest sitcoms of our generation. There are so many things I love about this show: the well-rounded characters, the jokes that don’t rely on stereotypes, and the way the show tackles real-world issues while staying true to its role as a comedy, to name a few. One thing in particular that sets this show apart is the annual Halloween heist episodes. Since the show (sadly) ended in September 2021, this is the first year that fans have a full set of heist episodes to binge-watch — which is exactly what I did.

Spoilers ahead!

What are the halloween heists?

The annual Halloween heist began in season one, when Jake made a bet with Captain Holt that he could steal Holt’s medal of valor by the end of the night. Since then, once per season, the squad would come together and compete for an object. Whoever has the object by midnight is crowned an “Amazing Human/Genius” (“Amazing Detective/Genius” for the first three seasons) and is granted ultimate bragging rights. What I love most about the heist episodes is how unpredictable they are: I love seeing the characters team up, betray one another, and spend ludicrous amounts of money on their extravagant plans. Here is my definitive ranking of the “Brooklyn Nine-Nine” Halloween heist episodes.

8. “cinco de mayo” (s6e16)

This episode actually took place on Cinco de Mayo, not Halloween, to distract Terry, who is nervous about his upcoming lieutenant’s exam. However, at the end Terry surprises the squad by revealing that he already took the lieutenant’s exam and passed and faked his nerves in order to win the heist.

Even though I ranked this episode last, I still really enjoyed it (which shows how great these episodes are). My favorite part of this episode was watching Jake and Amy tase each other with the Christmas gifts they gave each other the year before. But it’s not technically on Halloween, so it’s hard to compete with the others./

7. “Halloween ii” (s2e4)

“Halloween II” is Jake and Holt’s rematch from the first heist, but this time Jake attempts to steal Holt’s watch. He hires a pickpocket to grab the watch but is shocked when the thief refuses to give it back. Jake is sent on a wild goose chase trying to retrieve the watch. At the end of the episode, it is revealed that the pickpocket was actually hired by Holt, who tricked Jake and pulled off a win.

This episode solidified that the heist episodes were here to stay. I like this episode a lot, but not as much as I like the episodes from season three and beyond. It adds an extra layer of fun and unpredictability once the entire squad gets involved in the competition.

6. “halloween” (s1E6)

This was the episode that started it all, when Jake attempts to steal Holt’s medal of valor. Throughout the episode, we are to believe that Jake is losing, but at the end, we realize that everything went according to plan. With the help of the rest of the squad, Jake manages to steal Holt’s medal and becomes the very first winner of the Halloween Heist. 

Like I said before, the reason this episode isn’t ranked higher is because it’s much more entertaining when the entire squad is competing. However, this episode deserves a lot of love, since it began a wonderful tradition.

5. “halloween iii” (S3E5)

“Halloween III” starts as another rematch between Jake and Holt. They each take turns picking teammates, but neither picks Amy–Jake is worried she won’t want to sabotage the captain, and Holt is worried that since she’s dating Jake, she won’t want to go against him. While Jake and Holt battle for the Halloween Heist crown, Amy sneakily pulls off her own plan and wins the third heist.

This episode was great because it was the first time we saw the squad working in teams against each other. I also loved the twist of Amy winning, since it was the first time someone other than Jake or Holt won.

4. “halloween iv” (s4e5)

“Halloween IV” is the first heist where the entire squad partners up to win the heist, adding more surprise twists and betrayals. After Holt blindsides Jake by picking Charles (Jake’s best friend), Jake and Gina steal the Halloween Heist plaque right before Gina crashes into a wall and knocks her teeth out. After Gina leaves, each pair somehow ends up with a fake plaque and guesses that Terry was the one who tricked them. But when they race to blame him, Gina reveals that she was the one who took the real plaque, and pretending to knock out her teeth was all a part of her plan.

I love Gina, so I am a big fan of this episode. I loved the addition of partners in the heist, especially getting to see the “Sleuth Sisters” (Amy and Rosa) working together. This is also the first episode where we meet Bill, a random man Jake found who looks exactly like Charles, who becomes a prominent figure in the rest of the heists.

3. “valloweaster” (s7e11)

This heist takes place across three holidays: Halloween, Valentine’s Day, and Easter. The squad tries to steal “infinitude gems” (generic infinity stones from the Avengers) in this episode, and the heist is delayed twice after Cheddar and then Scully swallow the gems on Halloween and Valentine’s Day. Ultimately, on Easter, Rosa pulls off a win (and check out how awesome her reveal was).

I love this episode because Rosa is one of my favorite characters, and she was long overdue at this point for a heist win. Plus, since she collected the gems on all three holidays, she became the only three-time heist winner in the squad.

2. “the last day” (s8e9)

This episode was actually the series finale, where the squad planned one final heist before Holt, Amy, and Jake all left the 99. I loved this episode because, since it was the finale, the writers snuck in lots of callbacks to jokes from earlier episodes and brought back lots of the significant guest characters (when I saw Gina pop up, I actually screamed). 

I thought it was so fitting to end the show with a heist episode, because the heists have become so integral to “Brooklyn Nine-Nine.” It made the ending a little less sad to see my favorite characters heisting.

1. “halloveen” (s5e4)

“HalloVeen” is not only the best heist episode, but one of the best episodes of the whole show. In this episode, the characters are vying for a championship belt (or cumberbund, as Holt delicately puts it) that says “Amazing Human/Genius,” and Amy ends up finding it at midnight. However, as a surprise twist, Jake has altered the belt to read, “Amy Santiago, will you marry me?”
My heart simply cannot take how cute the proposal scene is, and for that reason, no heist episode can top this one. Plus, it’s fun to debate over who actually won the heist (I’m team Jake all the way).

Whether you agree with my rankings or not, I think it’s fair to say that the Halloween Heist episodes are some of “Brooklyn Nine-Nine’s” best. I loved getting to watch all eight heist episodes this year and highly recommend you celebrate spooky season by doing the same. Stream all episodes of “Brooklyn Nine-Nine” on Peacock TV and Hulu.

Jordyn is a junior at CU Boulder double-majoring in music and psychology. When she isn't writing her next article, you can probably find her reading, exploring restaurants around Boulder, or hanging out with her silver lab puppy.
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