Brooklyn Nine-Nine season 5: 18 Hints as Jake and Rosa Go to Prison

There will be no cop-out for these cops: Framed for bank robbery and found guilty in the season 4 finale of Brooklyn Nine-Nine, Jake (Andy Samberg) and Rosa (Stephanie Beatriz) are going to prison. Let's hope they're exonerated in time for Halloween, because some serious heisting awaits. There's also an important sneaker case to be solved, a dream job tempting Holt (Andre Braugher), and a big episode for Jake and Amy (Melissa Fumero) in the works. Want to unlock some of the secrets of season 5? Before the Fox cop comedy returns Sept. 26 at 9:30 p.m. ET/PT, read these 18 hints from Samberg and Brooklyn co-creator Dan Goor.

Much like how last season kicked off out of the precinct — Jake and Holt were stashed in the witness protection program down in Florida — the first few episodes of season 5 will go for disorientation with a pair of detectives in the slammer. "It's fun to see Jake on the other side of the looking glass," says Goor. "Here, all of his protection has been stripped away, all of this advantages have been taken away — his squad, everyone he relies on. It’s really Jake at his most vulnerable and having to live off of its wits, and that was exciting."

How does Jake manage his new environs? "Jake is crafty and he’s a survivor," says Samberg. "I was trying to remember that Jake’s not me — like, he actually is tough and street-smart. He’s in a very precarious situation, but he’s got his wiles. But obviously, he’s terrified as well. Probably more than Rosa, even." (More on that in a bit.)

Were the producers worried that prison was too dark of a fate for Jake and Rosa? "We felt like we should try to put him in prison, and once we broke those episodes, we were very happy with the decision," says Goor. "In some ways, the concept of doing prison was scarier than the reality of doing it.... We are aware that we’re a comedy show, but given that, we have tried to make it clear that prison is not a fun place to be, especially if you’re a cop. And that danger abounds."

Perhaps Jake should watch his back — and the rest of himself — while behind bars, as he will be surprised to discover that his new cellmate, Caleb (Tim Meadows), is... a cannibal. Or maybe this is the beginning of an unusual friendship. "Caleb is a cannibal who doesn’t feel like that defines him," says Goor. "He would rather be defined by his passion, which is woodworking. He is a very pleasant guy and insofar as Jake has a buddy in Charles, he is Jake’s jail Charles. Also it should be noted he is a fan of unusual food, just like Charles."

Adds Samberg: "Tim is so good, and he and I have a bit of rapport now because we did Popstar together, so I was very excited when they told me they were considering him for it. Especially because cannibalism is such an awful thing. To try to throw that into a comedy and ask people for it to be humorous, you need somebody who’s just infinitely likable, and he definitely fit that bill."

In need of protection, Jake seeks out the criminal mastermind of the prison, Romero (Lou Diamond Phillips). But, as Goor explains, "he finds himself between a rock and a hard place. The rock is Romero and the hard place is the warden (Toby Huss). The warden doesn’t like Jake. As far as he is concerned, there’s nothing worse than a dirty cop, which is what he believes Jake to be."

Samberg notes that Jake's main objective is simply to stay alive. "He wants to live and get home to Amy that’s really all he can think about," he says. "But it gets pretty hairy for him. He’s definitely walking a very thin tightrope. He’s like that guy from Man on Wire, except he’s not cheating on his wife."

As it turns out, Rosa is having a slightly easier time in adjusting to jail. "She, for instance, quite enjoys solitary and has no problem starting prison riots in order to be respected," notes Goor. "In the first episode, we see her interacting with Terry (Terry Crews) and Holt (Andre Braugher), who are trying desperately to make her life as good as they can."

"It’s more than an episode but it’s not a lot of episodes," shares Goor. "The most fun world for the audience — and for us as writers — is definitely Jake and Rosa back in the precinct, and especially since we know they were wrongly convicted, we don’t want to punish them or our viewers by putting them in jail for too long. That said, the episodes we do in jail are really strong episodes that explore new dimensions."

While Jake and Rosa idle in prison, the rest of the Nine-Nine detectives are chasing down leads that might help free their friends. "There’s a possibility for a shortcut that would be unethical," says Goor, "and they must decide whether or not to take that shortcut toward getting information that would clear Jake and Rosa." That shortcut involves Prison Break vet Paul Adelstein, who guests as the head of a prominent crime family.

After Jake gets out of jail — whenever that happens — he will pair up with Charles (Joe Lo Truglio) and Holt to look into a breaking-and-entering case at a shoe store. "A Yeezy-style sneaker has been stolen, so Jake, Charles, and Holt must go into that world to solve that case," says Goor. "It's an old-school romp, but Jake faces unexpected complications."

Goor calls this fifth installment "one of our best Halloweens yet" with "fun new twists and turns" within the heist format. "The stakes for Jake are higher this year than ever before," says Goor, adding: "Right off the bat, the conceit is anyone can win. It’s open to all takers." (While previous editions have involved the theft of a watch or a crown, strap in for this year's prized possession: A championship belt.)

"Every year it escalates where it's like, 'This is the year that’s the most important!'" notes Samberg. "I love doing those episodes so much. It’s one of the free-pass moments every season where we get to do just bonkers comedy, where any character could do anything because they’re so competitive."

Gershon's cunning and dirty Lt. Hawkins, who framed Jake and Rosa, will pop up again in the beginning of the season. "She remains a worthy adversary early in the season," says Goor. "They do battle with her once again early in the season."

At the end of season 4, we learned that Gina (Chelsea Peretti) was carrying the child of Boyle's cousin (Ryan Phillippe), and the baby to come will be named the Enigma or the Enigmo. But you'll have to wait a bit to delve back into Linetti's world. "We find out right away that she in on maternity leave," says Goor, who estimates that Peretti herself, who gave birth to a son this summer, will be on maternity leave through the first 10 episodes." That said, he hints cryptically: "She may or may not make a brief appearance in Halloween."

Be it via an old mattress or an "I love you," or an "I love you so much," Jake and Amy seem to keep taking their relationship to the next level. Will that happen again this season? "We definitely deal with their relationship," says Goor. "There’s a really fun, funny relationship story early on that I don’t want to say too much about. "

What exactly is in store for these crazy, totally-off-the-rails lovers? "There will be big changes in the Rosa-Pimento relationship," says Goor, promising "meaty" personal stories for Rosa. And what has Pimento (Jason Mantzoukas) been up to? "Pimento had a great time in Argentina," says Goor, "where he was beaten mercilessly after withdrawing money at the ATM machine."

Ever the gourmand who strays into odd culinary corners, "Charles may try to commercialize his interest in bizarre food," says Goor.

If you thought you wouldn't see Terry dressed as a shirtless warrior again — after he worked a death-threat case in season 4 involving the author of the Game of Thrones-like book series The Skyfire Circle — you have gravely miscalculated: There will be a sequel. "Terry will probably have to go undercover in that world," hints Goor, "wearing nothing but the loins of a sheep at some point."

In unrelated Terry news, "yogurt plays a prominent part in his Halloween story."

It doesn't happen right away — think more along the lines of the middle of the season — but Amy will reap the benefits of passing that sergeant's exam last season. "We’d like to figure out a way to keep her in the precinct," says Goor. We’re conscious of the fact that sending her to a different precinct for more than episode is problematic."

We've seen him Wunched in the past, moving out of the precinct and into the world of PR. But this time he may have a dream job in his sights. "Holt is potentially tapped for a big job in the NYPD," says Goor, "and that puts pressure on him and the squad to be the best they can be. It’s a positive pressure as opposed to a negative pressure, which we’ve done in the past."

Instead of celebrating the show's 100th episode, "we’re only making a big deal out of the 99th," says Goor, quipping. "Whatever it is, it will end with all of them saying 'Nine-Nine!' at the end of it."

"Scully and Hitchcock spend over 48 hours on their butts," says Goor.