Damon and his partner Stacy, two cops, go undercover as a pimp and his hooker to nail Runuti, the owner of an escort service; Damon's brother Bernard is having marital problems, so he's sleeping on Damon's couch.

Damon goes undercover in a jail and tricks a couple of bank robbers into revealing where they've hidden the stolen money. Back at the squad room, the Captain announces it's time for the annual physical; no one's getting out of it, and that means Damon. Damon goes to get his physical, but when it's time for the prostate exam, he's gone.

Damon goes undercover on a drug money laundering case and encounters Ally, a sexy Jamaican girl whose accent makes him fall in love; there's instant chemistry, and Damon adopts his own Jamaican accent just to make it interesting.

After Damon makes a successful bust at the airport, Tracy Warren, a Chicago Sun Times reporter, tries to interview him, but Damon keeps hitting on her. Damon's neighbors down the hall are moving, and he realizes that a perfect way to get rid of Bernard is to have him move into their apartment.

Damon's doing everything he can think of to get Tracy to go out with him. Bernard, feeling protective of his new roommate, tells Damon to back off; Tracy's coming off a bad divorce and she needs her space.

There's money missing from a gambling bust, and Internal Affairs suspects the Captain, Damon and his fellow detectives. Damon and Tracy have an incredibly romantic evening at his place that ends on a completely unexpected note.

Damon comes home after work, and Bernard tells him he has to leave right away; Bernard actually has a woman in the bedroom. The only problem is that Bernard told her that he's an undercover cop named Damon.

Damon, in full African garb, visits an antique shop in an attempt to bust the owner for selling illegal ivory. Woody Woodson, the famous actor, is hanging out at the precinct doing some research for his new TV series. Everyone, especially the Captain, is star-struck with the exception of Damon, who finds Woody's presence an annoying distraction. Damon's upset when the Captain informs him that Woody will be following him around for a few days.

Stacy and Damon are working on a fake designer clothing scam; Bernard meets a Chicago Bulls cheerleader while he's working his security job; Stacy, who's been having problems with her boyfriend, tells Damon that she and David are back together.

As part of an undercover operation against the Mafia, Damon shoots Billy in the foot at the Don's request. Bernard's positive that his estranged wife Janice is having an affair, but Damon promises to prove him wrong.

Damon and Stacy go undercover in a nursing home; Bernard is fast-talked by Sammy, the neighborhood con man, and loses half of the rent money; Damon and the Captain go on a stakeout in a parking garage in their ongoing attempt to vindicate her in the case of the missing gambling bust money.

Damon goes to a sporting goods store to buy some athletic shoes, but ends up buying a lot of camping equipment he doesn't want to impress Monique, the pretty sales clerk, and accepting a date to go camping with her and her friends. Billy has joined Big Brothers of Chicago; he brings his little brother Elvin to headquarters to sell candy for a school fundraiser.