When he hears that Doug Judy is headed for prison, Jake gives his old frenemy one last fun road trip.
Tropes
- The Alleged Car: To throw Doug Judy's gang off the trail, Jake buys a used clunker of a car. When he opens the door it comes off its hinges. The door is held in place with duct tape for the rest of the episode.
- Bait-and-Switch: The ending of the episode shows Doug Judy getting arrested and after some time, he chats with Peralta on phone, wearing an orange shirt. The implication being he is arrested, wearing his prison clothes and is talking through his one phone call. The camera eventually zooms out to reveal he is a free man, wearing an orange casual T-shirt and talking on a phone booth.
- Batman Gambit: Doug and Jake play a long game of this, but eventually Doug comes out on top using Jake's paranoia regarding him. He manages to bring Holt, Boyle and Trudy onto this.
- Bittersweet Ending: Doug is arrested, so Jake won’t face the consequences of unwittingly helping him escape. And the Pontiac Bandit manages to escape the police once again (and in the process it even allows involuntarily to arrest 3 other criminals including at least one much more dangerous than him). However, the stinger reveals thant Doug had to flee with his wife to Netherlands, and even if he is happy here, the sad look on Jake’s face shows that the later knows it'll be difficult for them to physically meet each other again.
- Call-Back: One of Jake's "sexy-ass surprises" for Doug was a call of Rosa serenading him as he did for her.
- Coordinated Clothes: Jake makes himself and Doug matching outfits with tigers and toucans ("Tigers and Toucs!") on them.
- Chekhov's Skill:
- Doug shows Jake how he can pick handcuffs with a pen. Jake slips one in his pocket when he's taken away to help him escape.
- Jake and Charles use the name "Estelle Minderman" as a code word to turn the tables on Doug Judy. Doug later drops this same name before disarming the goon holding Jake at gunpoint.
- Cryptically Unhelpful Answer: When Jake starts questioning whether the state troopers are actually Doug's accomplices, Doug responds with vague answers, leading Jake to doubt himself and veer away from them.
- Gag Penis: Trudy's small dog has giant testicles if the Pixelation and dialogue are to be believed.
- Graceful Loser: Doug Judy accepts his imprisonment in stride.
- Kansas City Shuffle: All over the place as no matter what Jake tries, Doug Judy is a step ahead and planning for it as part of the escape. Notably, he uses Jake's paranoia to make him think some cops helping are Doug's guys to trick him into heading off to meet his real gang.
- Karma Houdini:
- Thanks to Jake loaning a pen, Doug Judy manages to escape to Amsterdam.
- Trudy drives away after helping with Doug's escape and hiring cop-killing goons to pick him up.
- Mundane Solution: Compared to his amazingly complex scams of the past, Doug Judy simply swapping a few numbers and addresses in Jake's phone for his escape is surprisingly low-key.
- Never Going Back to Prison: Doug Judy's whole motivation in this episode.
- Out of Focus: With no other storylines on the episode, the rest of the cast only make small token appearances. Boyle and Holt are the only ones with significant roles on the plot.
- Put on a Prison Bus: Subverted. Being the last Brooklyn 99 episode focused on the relationship between Jake and the Pontiac Bandit, and this one being arrested by other cops at the end, one might think that Doug will finally be imprisoned, after spending the entire show escaping justice. And then, the Stinger reveals than Doug not only escaped from police one more time, but also managed to fly away from the United States.
- Road Trip Plot: Jake drives Doug Judy to prison himself to give his friend-slash-arch nemesis one last adventure together.
- Surprisingly Happy Ending: Doug Judy accepts his imprisonment and looks set to wait out his remaining years in prison and then Terry gets a phone from him to express his thanks... but then it turns out Jake slipped a pen into Doug's pockets as he breaks out of his cuffs and the prison, and escaped to Amsterdam with his wife.
- Surprisingly Realistic Outcome: Despite Jake purging Doug Judy's records, he could only do so for the state he works for (New York), so Doug still has criminal charges against him in other states.
- Doug Judy, despite being legit, has a hard time getting work due to his prior criminal record.
- To Be Lawfulor Good: After years of being a Rules Lawyer in regards to his friendship with Judy, Jake finally reaches the point of breaking a law to save Judy from jail. Making himself a willing accomplice in his escape by giving him a pen to get out of his handcuffs.
- Too Dumb to Live: Trudy hired the goons from Craigslist.
- Vitriolic Best Buds: In the end, Doug Judy can't let the goons Trudy hired shoot Jake and he fights them off even though it means going to prison. Doug also lets Peralta hug him before being hauled off, unknowingly giving Jake a chance to slip a pen into Doug's pocket provide an opportunity for an escape.
- We Named the Monkey "Jack": Combined with Punny Name, as Doug Judy's sister, Trudy Judy's, pet dog is named... Dog Judy.
