There are very few shows that have done as many holiday episodes as Brooklyn 99 has, and for good reason. Usually, holiday episodes can get stagnant and repetitive over the seasons, but the cop-comedy set in Brooklyn’s 99th precinct manages to keep doing it year after year.
It’s remarkable that NBC has kept the holiday-episode tradition alive for the sitcom due to the fact that the show no longer airs during the prime holiday season, and fans certainly aren’t complaining.
16 Mr. Santiago, Season 4 Episode 7
It seemed a little odd that only Amy’s father (Jimmy Smits) would come to Thanksgiving dinner in order to meet Jake instead of also bringing Amy’s mom along, but things got even odder when Amy invited the entire squad over for Thanksgiving dinner as well. Pimento was even there for this episode. Pair that with the low-blow move of Amy’s dad tricking/humiliating Jake and you get an episode as dry as Amy’s turkey.
15 Two Turkeys, Season 5 Episode 7
The second Thanksgiving episode in a row on the list isn’t much better than the first. The episode’s premise is better as it’s much more realistic for a Thanksgiving setting (Jake and Amy have both of their sets of parents over) but unfortunately, the episode doesn’t stray from the cliched “my-parents-don’t-like-your-parents” story-arc. The jokes were funny, but this was a second dud in a row for Turkey Day.
14 Thanksgiving, Season 1 Episode 10
Three Thanksgiving episodes in a row. Yikes. It’s not fair to knock a sitcom for wanting to include its cast members in whatever episodes they come up with, but the concept of spending a highly family-oriented holiday with your co-workers is quite overdone. The 99’s very first Thanksgiving has Amy invite the entire squad over (despite being a horrible cook) in order to impress Captain Holt, but he and Jake end up having to leave to work a case. The end of the episode was wholesome, but the rest was just so-so.
13 Halloween III, Season 3 Episode 5
The Halloween Heist episodes are fan favorites and audiences can’t wait to see who walks away with the title of “Amazing Human/Genius” every year. That said, the heist’s third attempt (where Amy got crowned Queen of the 99) was quite predictable as both Jake and Holt excluded her from the activities the entire night.
Include that with the fact that both Jake and Holt already had a win under their belts and the audiences got a surprise winner that wasn’t much of a surprise.
12 Lockdown, Season 2 Episode 7
Talk about a bad Thanksgiving. Not only is the precinct on edge to start this episode when Holt and Terry leave for the day and put Jake in charge, but things get worse when an anonymous package containing a mysterious white powder shows up at the precinct. They put the place on lockdown and everybody is (understandably) tense about the situation, but luckily the package turns out to be harmless.
11 Cinco De Mayo, Season 6 Episode 16
The first of NBC’s episodes to make the list is their first attempt at the Halloween Heist. When Terry reveals he’s on edge about taking his Lieutenant’s exam, Jake suggests a spontaneous heist to calm his nerves. As usual, the heist wasn’t spontaneous and everybody carries out their plans, with the surprise winner being Terry, who also reveals that he’s already passed his exam.
10 Halloween IV, Season 4 Episode 5
The episode that gave Brooklyn 99 fans their favorite Boyle-look-alike was the fourth annual Halloween Heist. The writer’s learned their lesson after season 3 and led everybody to believe that Terry would be the ‘surprise’ winner this season, only to pull a double-twist and have Gina take home the coveted title of “Amazing Human/Genius”.
9 Captain Latvia, Season 4 Episode 10
Boyle and his wife were lucky enough to adopt a child from Latvia at the end of season 3 and his son made several appearances, including this Christmas episode where Charles tries to find a back-ordered toy for Nikolaj that was stolen by the Latvian-mafia.
The lesson in this episode is heartwarming as Charles fails to get the toy but Jake ends up bonding with Nikolaj for the first time.
8 Valloweaster, Season 7 Episode 11
This season 7 episode gave audiences the gift of three holiday episodes in one, combining Halloween, Valentines Day, and Easter. The precinct members split off into teams and try to steal the gems for the Infinity Gauntlet, only to be stymied twice when the gems get eaten by Cheddar, then Scully. On Easter, Rosa takes home the prize and reveals that she actually won on all three holidays as well.
7 Christmas, Season 1 Episode 11
The very first Jake-Holt episode was one for the record books as it had Peralta assigned as the personal bodyguard for Holt after a threat had been made against his life. Holt tries to play the threat off as a hoax, but it’s revealed to be coming from one of Holt’s old enemies – the Freestyle Killer. The 99 comes to Holt’s aid and bring down the criminal, but Boyle takes two bullets to the butt in the process.
6 Halloween II, Season 2 Episode 4
While the winner of this heist was just as predictable as season 3 (nobody expected Jake to win twice in a row) the episode itself became an instant classic due to the detailed and clever final-reveal. Jake had planned a three-month long heist and was confident in his abilities to outwit his Captain, only to fail miserably due to Holt revealing he had been planning the heist for the entire year.
5 Halloween, Season 1 Episode 6
The episode that started one of the greatest staples of Brooklyn 99 was also one of the best. Jake makes an ill-favored bet with the Captain that he can steal his medal of valor by midnight on Halloween.
Throughout the night Jake gets stopped at every turn and seems as though he’s going to fail – only for the classic heist twist to turn up and reveal that the entire precinct was helping him as he takes home the title.
4 Ava, Season 3 Episode 8
With so many sub-par Thanksgiving episodes it was only fitting for one of them to make the Top 4, especially considering the episode had one of the series best cameos to date. When Sharon (Terry’s wife) goes into labor in the precinct on Thanksgiving (and won’t go to the hospital) Captain Holt is forced to ask his ex-boyfriend, Ava (Nick Offerman) for help. Between the wooden-duck banter and Ava’s magnificent beard, Nick Offerman’s guest appearance was all this episode needed.
3 The Pontiac Bandit Returns, Season 2 Episode 10
It wasn’t exactly a Christmas episode (more Christmas-themed) but the first return of Doug Judy had audiences elated nonetheless. When Doug Judy finally gets captured and turns over the head Giggle-Pig distributor in Brooklyn in order to reduce his sentence, he seizes the opportunity to escape from Peralta and Rosa for the second season in a row. Jake and Rosa nab the Giggle-Pig pusher, but Doug Judy lived to see another season.
2 Yippie Kayak, Season 3 Episode 10
Botched catchphrase aside, this episode was arguably the greatest spoof episode that Brooklyn 99 has ever done. Despite being in a store instead of a hotel, Jake, Charles, and Gina find themselves locked in a store with some high-level robbers in a classic Die-Hard situation. Jake and Gina end up getting caught and Boyle saves the day, but he also predictably botches the film’s classic catchphrase in the process.
1 HalloVeen, Season 5 Episode Episode 4
The ultimate Halloween Heist episode may never have an ultimate winner (Jake, Amy, or Holt) but the twist at the end was easily the most surprising/most heartwarming and fans couldn’t have been more thrilled. The precinct decides to try and steal a championship cummerbund for the title of “Amazing Human/Genius” but at the last moment, Jake replaces it with a marriage-proposal cummerbund and asks Amy to marry him. This episode was toit.
About The Author
