Bull turns down a major pay day for his company in order to assist a cook accused of murdering his socialite fiancé when he realizes the man's confession to the crime was coerced by the police. Also when Marissa, Cable, and Danny find out Chunk is going on a date with a man he doesn't know well, they try to convince him to use their collective skills to investigate him beforehand.
Charles Ponzi hires a publicist to improve his image Sadie the Goat becomes a notorious Hudson River pirate a con man poses as a Scottish royal.
Kelley is angry with Sierra after he finds out how she treated a member of the deck team. Emily enjoys a night out with Ben while things get very heated between Kate and the exterior crew. Kyle puts on the charm when he gets his wish and takes Sierra out on a date, but things don't go exactly as planned.
Katie, jealous of Taylor’s friendship with neighbor Viv, reluctantly competes in the Westport Halloween “Zombie Run” after she finds out they’ll both be running. Meanwhile, Greg and Anna-Kat get a little too much in character for the “zombie” part of the run’s obstacle course.
Todd offers to help Savannah, who wants to buy a home, but she realizes that there are too many strings attached Grayson's monthly phone bill gets him in hot water with Todd.
Mr. Kim is frustrated with Frank, a repairman who talks too much, while Janet's cousin Nayoung visits from Korea, challenging Janet's sense of what it means to be 'Korean.' Jung and Shannon get tickets to a basketball game, but Jung starts to wonder if Shannon thinks it's a date
Earn wakes up in another woman's bed and Van comes by to pick him up for a Juneteenth-themed party which she believes will help her establish good networking. The luxury home's owner is a rich White man who is shown to know quite a lot about Black culture in an anthropological way and his bourgeois Black wife. To impress the party's attendees, Vanessa and Earnest have to pretend they are a married couple who love fine art. Earn ends up going off on the homeowners when the wife insults Paper Boi and his hip hop management career after he is outed by some valets. On the drive back home, Earn and Van have sex in their car.
Mike must convince Gary that Candle Cove is behind the murders before he takes justice into his own hands Marla, Jessica, and Amy frantically search for Mike before it's too late.
It's all in the details when the artists must create powerful designs for Dodge Chargers.
Nitin is getting a haircut, because Nat's fixed him up with a date and Nitin badly 'wants some'. Meanwhile, PC Harris calls an Emergency Strategy Meeting at Children's Services.
Louis tries to get Jessica into the Halloween spirit, but she's busy writing her first horror novel. In the meantime, Emery and Evan debate what costumes to wear and Eddie is excited about partying with high schoolers at Nicole's house.
Casey seeks help with a personal matter from Susan Weller. A rich party guy wants Severide to travel with him. Stella tries to help a sick street kid. Otis and Herrmann share their concerns about Molly's lack of customers.
From prison, Cosimo asks Contessina to try bribing a member of the Signoria, to buy votes in his favor. Albizzi starts poisoning Cosimo's food through his prison guard. Contessina negotiates exile rather than the death penalty.
Sean Farmer travels to a remote campsite in Virginia for a fishing trip with his friend Scott Johnston. When a mysterious stranger appears, the area’s dark past returns to haunt the campers.
The team join forces with the FBI to investigate a plane crash in the bayou that left three sailors dead. Meanwhile, Sonja and Lasalle interview candidates for the open agent position.
Albizzi has managed to foment the citizenry against Cosimo, accusing him of the crime of usury. When Cosimo learns of the situation, he decides to return to Florence. Albizzi then invents a ploy to get Cosimo arrested and held for trial.
When Halloween arrives, or what Kenny refers to as the gay Super Bowl, he plans to go to Boystown to watch the festive costume parade. In an effort to prevent Kenny from attending, Eileen agrees to let him throw his own Halloween party at home. Eileens tolerance is ultimately tested when Kenny recruits Stuart and his gay friends to join the big party, and he makes a BIG costume change. Meanwhile, Jimmy and Shannon plan to pull off an epic Halloween prank.
"Documentary Now!" parodies the current obsession with documentaries. Season one features six different stories and stylistic approaches paying tribute to the doc format.