Brooklyn 99 quickly won over its audience when it debuted in 2013, with the goofy and lovable Detective Jake Peralta leading the fight against New York City’s underworld, with the help of Captain Raymond Holt, Sergeant Terry Jeffords, and his rag-tag group of fellow detectives.

With most cop shows being predictable dramas set around a Superman-esque hero, the fun-spirited comedy was a refreshing change of pace for the boys in blue. However, despite a strong freshman year, Brooklyn 99 truly made a name for itself among the greatest comedies on cable during its second season. With the addition of Holt’s nemesis, Deputy Chief Wuntch, as well as furthering the drama of Jake and Amy’s relationship, season 2 was assuredly one of the best. Here are the top ten episodes of season 2 according to IMDb.

10 The Mole, Episode 5 (8.2)

The 99th precinct ran into some serious internal problems during this episode with the revelation that they had a mole leaking sensitive information from within their own walls and had a lieutenant from Internal Affairs show up to investigate.

Jake, in an attempt to clear his own name of possibly being the mole, investigates the matter himself and stumbles upon Boyle and Gina in the middle of a “friends with benefits” moment, causing him to question everything he knows about his friends/colleagues. Eventually, he and Holt uncover the truth – there was no mole and the lieutenant was actually just a spy sent by Holt’s enemy, Wuntch, and the two of them turn the tables on her.

9 Jake & Sophia, Episode 6 (8.2)

This one had audiences divided. On the one hand, we were all still rooting for Jake and Amy to get together – but on the other hand, Sophia was a really, really good fit for Jake. Jake and Amy’s relationship seemed to be at a complete stand-still by this point in the season with Amy firmly established in her relationship with Teddy, so Jake decided to test his luck in the dating pool.

He ended up with Sophia, a beautiful defense attorney with who Jake seemed to immediately hit it off despite their difference in jobs and opposing views toward criminals.

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8 The Road Trip, Episode 9 (8.2)

Season 2 was definitely the season of relationships – Boyle and Gina as well as Rosa and Marcus to name a few, but the main relationship that audiences have been rooting for since episode 1 was the one of Jake and Amy, and this episode gave viewers their first true glimpse of hope that it could happen.

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When Jake and Amy have to take a trip upstate to a BnB the night before they transfer a perp home, they invite their significant others (Sophia and Teddy) to come along. But things go awry and not only does Amy break up with Teddy during the trip, but she also reveals that she had a crush on Jake in the recent past. True fans were cheering at the end of this one.

7 Jimmy Jab Games, Episode 3 (8.3)

Your tax dollars at work, ladies and gentlemen. Everybody has days at work where there are lolls and it seems as if there’s absolutely nothing to do – turns out, so do cops. When the 99 gets reserve parade duty and are instructed to stay in the precinct all day long (with no Holt or Jeffords present) Jake knows exactly what to do.

The Jimmy Jab Games, an Olympic series of random games such as eating month-old Chinese food, running an obstacle course in a bomb suit, and several others. Amy takes home the Gold (thanks to Jake) and wins the only non-broken chair in the precinct.

6 Beach House, Episode 12 (8.3)

Just like everybody needs an occasional break during work, everybody needs the occasional break away from work – however, they don’t usually take those breaks with the people they work with (that’s a sitcom, for you). The detectives of the 99 go on their annual trip to Charles’ beach house in February to get away from the stress of the big city.

But when Captain Holt decides to show up and partake in the vacation, his stoic presence puts a damper on the drunken festivities. After a talk with Jake, Holt eventually comes around and loosens up with his subordinates.

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5 Windbreaker City, Episode 15 (8.3)

While Community will always be the reigning champion of “Best Paintball-Themed Episode” in a comedy show, Brooklyn 99 gave it their best shot. After the success of the first season episode, Tactical Village, the 99 followed it up by getting themselves invited to a simulation of a hostage situation constructed by Homeland Security.

However, the big-bad federal agents just want to make fun of the lowly cops and the 99 decide to fight back by taking over the entire drill and wiping out nearly all of the agents in the process. The Die-Hard move at the end was a cheap-shot, by the way.

4 The Pontiac Bandit Returns, Episode 10 (8.3)

You’d be lying if you said you didn’t look forward to the Doug Judy episode for every season of Brooklyn 99. Since the very beginning, guest star Craig Robinson shows up for a single episode every year to cause shenanigans with Jake and the gang and this was the episode that got the ball rolling.

Despite his escape a year earlier, Doug Judy shows up just in time for Christmas and gets himself caught by Jake and Rosa, only to set up a deal for his freedom by giving up the head GigglePig distributor in the city. In typical Pontiac Bandit fashion, the deal was a double-cross and Judy escapes once again.

3 The Chopper, Episode 22 (8.6)

Despite Brooklyn 99 being a goofy comedy, this particular episode was one of the few that resembled an action-packed blockbuster. When one of four men who stole $21 million several decades earlier gets murdered, the 99 looks into the crime and thinks that one of the other men is behind it.

The case quickly turns into a triple-murder homicide that involves taking a helicopter to an abandoned barn upstate and discovering the $21 million in a safe in a basement. Be honest, that doesn’t sound like your typical comedy-show premise.

2 Halloween II, Episode 4 (8.8)

While the show has plenty of recognizable running jokes, gags, and staples, the one that audiences look forward to the most every year is the Halloween Heist episode. Beginning with Jake surprisingly besting Captain Holt in season 1, this episode was the dramatic sequel where Jake challenges the captain to yet another heist attempt.

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Holt eventually accepts the bet and hilariously humiliates Jake in the process by revealing that he was planning his own heist for an entire year. In this, episode Holt truly was an amazing Captain/genius.

1 Johnny & Dora, Episode 23 (9.1)

We’d been waiting two whole years and this was the episode that it finally happened! No, we’re not talking about the first episode that Brooklyn 99 ranked higher than 9 stars on IMDb (though it was). We’re talking about how Jake and Amy finally got together in the season 2 finale thanks to an undercover operation where they posed as a couple, Johnny & Dora.

Despite the fact that they took down the bad-guy and Jake and Amy kissed for the first time, the episode seemed to be ending with a heart-wrenching moment with Captain Holt forced out of the 99. Luckily the wound was satiated by Jake and Amy kissing, for real, after his untimely departure. Noice.

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About The Author


Jonathan Meschutt
(212 Articles Published)

Jonathan Meschutt is a writer based in Upstate New York. He’s had every job you could think of, including garbage man, dishwasher, administrative assistant, catering cook, and a dozen more, but now works as a list writer for Valnet Inc, and is covering entertainment topics for Screen Rant. He has a B.S. Mass Communication degree, focused on Film (see what he did there?) and has spent the past three years as the writing assistant to an Emmy nominated television screenwriter.

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