The 10 Funniest ‘Brooklyn Nine-Nine’ Flashbacks

It turns out you can laugh at the past as much as you can learn from it
The 10 Funniest ‘Brooklyn Nine-Nine’ Flashbacks

Brooklyn Nine-Nine’s flashback sequences are as crucial to understanding its cast of characters as their Halloween heist strategies and the titles of their sex tapes. Through these off-screen/on-screen moments, we learn that Rosa (Stephanie Beatriz) has a mysterious and confusing past, Jake (Andy Samberg) has had some truly unfortunate hairstyles and Holt (Andre Braugher) has never expressed a non-Cheddar-related emotion. These vignettes all landed harder than Captain Peralta the day after a bender, but some landed harder than others.

Jake and Amy First Meet

Speaking of unfortunate hairstyles, this scene takes place in 2009, a time when neither the Melrose Place nor the Howard Stern were in fashion. Is that pretty much the only joke here? Yes. But it’s a comedic achievement to make Boyle (Joe Lo Truglio) look chic by comparison.

The Freestyle Killer

It’s always fun to see Captain Holt in the 1980s, but he’s in particular Miami Vice form when he tracks down the Freestyle Killer. His “Marco Polo” line is even dangerously close to a joke. Was it a great idea to taunt a man who killed an entire 4x100 meter swim team with all the swimming he was going to do while he was in prison? Probably not, but it all worked out in the end.

Holt’s Model Trains

There’s a world of insight provided by the fact that Captain Holt’s happiest childhood memories involved keeping a strict model train schedule, even if it meant doing nothing but patiently staring at the track for 45 minutes. Special mention also goes to Baby Holt’s interpretation of “playing doctor,” i.e., informing his teddy bear he had cancer and should get his “house in order.” He may not have been the most fun playdate, but he was the most realistic.

Rosa’s Dark Past

Rosa is a bundle of contradictions. She’s accomplished in the use of a cornucopia of weapons, has been buried alive and has a side hustle restoring vintage cars for celebrities. But underneath her tough exterior, she’s a former ballerina, devoted dog mom and even more devoted Nancy Meyers fan. Her “deepest shame,” however, is her time as a competitive gymnast. It did leave her with the ability to scale walls, so if anything, it just made her even more badass.

Rosa on the Stand

Thanks to Rosa’s no-nonsense attitude, you could say she’s not the best witness for the prosecution. She insults the jury, the victim and even threatens the court reporter. To be fair, those stenography machines are really annoying.

Hot Hitchcock and Scully

This flashback finally answered the question, “Why haven’t Hitchcock (Dirk Blocker) and Scully (Joel McKinnon Miller) been fired?” It’s because they used to be impressive (and hot) enough to warrant their own TV show. It’s hard to let guys like that go, no matter how many sinks they set on fire. The same is probably true for your awful boss.

Terry’s First Case

This one really has everything: Haircuts that were already dated, circus trash, kittens, Terry Crews holding kittens. It would have been a much better episode if the cat had turned out to be the perp, but Crews still ended up being right, so who’s to say? Coffee's for case-solvers.

Why Charles is Sterile

It’s moments like this where the Brooklyn Nine-Nine team really shines. A lesser production would have cut at the first dick hit. What makes the joke is letting Boyle get hit in the dick over and over, in rapid succession, while time otherwise stands still. Incidentally, this is also our only Mortal Kombat strategy.

Don’t Eat the Burrito

There’s so much going on here. Why so many towels? How long has Jake been in that hot tub? How did the burrito get in the water? (Is that why he’s crying? He dropped his burrito? Been there, buddy.) What’s important is we’ve all eaten our share of shame burritos.

Terry’s Incident

We could break down what makes Terry’s fatherhood-anxiety-induced dummy shooting spree so funny — the juxtaposition of the uncomfortably real threat of jumpy cops with the harmless targets, Jake’s understated reactions, his fucking face. But let’s be honest: It’s his scream. Terry Crews is a grade-A girly screamer. Actors could train their whole lives and never replicate it, which is just one trick in the bag of magic that is Terry Crews.

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