The Pontiac Bandit was introduced in Brooklyn Nine-Nine from the first season and has made an appearance at least once every season since. Doug Judy, the bandit's true identity, has created a complicated relationship with Jake Peralta. Doug is Jake's archnemesis that he gets along with great and Jake is Doug's best friend.
Throughout the years, Jake and Doug have had their ups and downs. Some moments they truly acted like good friends while other times they did things that hurt one another. The dynamic between PB&J, Pontiac Bandit & Jake, the moniker Doug gave them, continues to bear hilarious fruit.
BEST FRIENDS: Karaoke Together
Doug reaches out to Jake for help when a powerful criminal he stole from wants recompense. But they take a little time for fun in the middle of the case. They rent a karaoke room to make a call for a drop and realize they have a few hours before they need to get going.
The scene cuts to Jake and Doug screeching out the lyrics to "What's Up?" Even after Doug Judy escapes and returns the diamonds he stole, he leaves them in the karaoke room where a pre-recorded version of him sings with Jake.
NOT FRIENDS: Doug Double Crosses Jake
During the case with Rosa where Doug reached out to Jake for help, the Pontiac Bandit returned to his old ways and double-crossed the gullible detective. Jake believed in Doug and left him in an alley with the stolen diamonds while he chased the criminal lord that wanted Doug to repay him.
It's a moment that truly hurt Jake, as he let himself get swept away in the bromance. Doug took advantage of Jake's trusting nature and used him to get away scot-free.
BEST FRIENDS: Jake Keeps In Touch With Doug's Mom
Although Doug Judy is on the run and Jake knows he's a criminal, the goofy detective still keeps in touch with Diane, Doug's mom. Whenever Doug makes his way back into Jake's life, Jake and Doug always talk about her. Jake never fails to mention how much he loves Doug's mom.
Perhaps it is because Jake has a soft spot for mothers in general as he is so close to his own mother. Regardless, he doesn't let his complicated feelings for Doug get in the way of his connection to Diane.
NOT FRIENDS: The Cruise Escape
Jake and Amy mysteriously won a free cruise vacation only to find out it was all planned by Doug Judy. Once more, Doug needed Jake's help getting away from a murderer that wanted him dead. Jake didn't want to play along this time and tried to get the ship's captain to arrest him, but couldn't.
In the process of trying to keep eyes on Doug, Jake neglects Amy's desire for a real vacation. The bandit plays him like a fiddle and escapes once more.
BEST FRIENDS: Jake Sings At Doug's Funeral
Jake gets word that Doug Judy is dead and attends his funeral, where he keeps up his pretense as Doug's assistant Mangy Carl. Doug's sister asks Jake to sing at his funeral, but Jake is hesitant at first.
When given the alternative to talk about how Doug took him in and away from a life of prostitution, Jake takes the option to sing instead. The childish detective proceeds to sing a ridiculous song made up on the spot when he catches sight of Doug Judy, still alive and well.
NOT FRIENDS: The Initial Dupe
Jake is unaware that Doug is the Pontiac Bandit when they first meet. Doug is a witness in Rosa's case and claims to know the thief and how to get in touch with him. The first episode with the Pontiac Bandit is a series of shenanigans where Doug leads the detectives on a wild goose chase.
Jake thinks he and the low-life are bonding, but it turns out Doug has been playing them the whole time. He sets up his barber for the fall and escapes Jake, catalyzing a complicated friendship.
BEST FRIEND: Doug Helps Capture George Gessilnick
Jake finds out that an escaped prisoner named George Gessilnick has ties to his frenemy, the Pontiac Bandit. He calls in Doug Judy for help in finding his former foster brother. Doug openly hates his brother and calls him a bad and scary dude.
Doug agrees to help with the case and works with Jake and Rosa to bring in George. He even helps Captain Holt replace Gertie in the process, through legal means of course. Things were touch and go, but Doug pulled through and did the right thing.
NOT FRIENDS: Doug Pretends to Betray Jake
When Doug helps Jake recapture his escaped convict brother George, the only way to do it is to double-cross Jake and Holt. Jake feels stupid for getting tricked again, but it turns out Doug's betrayal is a triple-cross, as he wants to gain George's trust to take him down.
But the ploy is confusing and hurtful, as he says terrible things about Jake to George. Jake hears them and feels the sting, as even with their complicated history, he still considers Doug a friend.
BEST FRIENDS: Doug Invites Jake to His Wedding
It happens in a roundabout way, but Jake eventually gets the invite to Doug Judy's wedding. At first, he finds out about the wedding when Rosa picks up another criminal with an invitation, and Jake realizes he doesn't have one.
Jake is hurt that after going straight, Doug Judy doesn't keep in touch with him. But Doug does want him at the wedding. He even asks Jake to be his best man. He just needs to tie up some loose ends first.
NOT FRIENDS: Jake Arrests Doug's Friends At His Bachelor Party
Jake confronts Doug about the lack of a wedding invitation and Doug claims it is because he can't have a cop at his wedding where so many of his friends are former criminals. Jake assures Doug he can be cool, and Doug invites Jake to his bachelor party.
But Doug's friends commit a crime and Jake can't turn the other cheek. Even though they pull a reverse heist to return the jewels, Jake still calls in a SWAT team to arrest Doug's friends. But it turns out, Doug is banking on this.