Damon (TV series)

Damon and his partner Stacy, two cops, go undercover as a pimp and his hooker to nail Runuti, the owner of an escort service; they bust him but have to release him because the camera broke and they have nothing on tape. Damon's brother Bernard is having marital problems, so he's sleeping on Damon's couch. Damon says Bernard's problem is that he has no idea how to communicate with women. Billy, the clueless new guy, arrives at work and immediately becomes the butt of everyone's jokes. Bernard, who's a security guard, is embarrassed when two thugs rob the shop where he's ordering coffee and leave him tied up. The Captain calls Damon into her office, announces she's about to re-enter the world of dating and asks for his advice; he suggests that his "hard as nails" boss needs to soften up a little bit. She tells him he has two days to wrap up the Runuti case or she's pulling him off it. Bernard complains that Damon doesn't support him in his career, so Damon says Bernard can accompany him as he tries once again to bust Runuti. Dr. Helen Troy, the police psychiatrist, holds a sexual harassment seminar in the squad room, which is quickly reduced to chaos by Jimmy, Damon, Stacy and Carrol. And Damon and Bernard bust Runuti, and Bernard couldn't be more proud and happy.

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. Bernard tells Damon he didn't get a promotion he thinks he deserves, so Damon gets Bernard pumped up and sends him off to demand the job. Damon goes to get his physical, but when it's time for the prostate exam, he's gone. Bernard reports back to Damon that he demanded the promotion and was fired as a result; now Bernard's in despair that he threw away the best job he ever had. So Damon shows up at Bernard's office claiming to be Bernard's replacement sent by the head office; he suggests that they plan a series of break-ins at the homes they've been hired to protect. Bernard's boss is horrified and offers to re-hire Bernard immediately so he can throw Damon out. Bernard says he'll only throw him out if he gets the promotion, and his boss gives in. And Damon bites the bullet and takes the prostate exam.

Damon has a one-night stand with a girl, Brenda, who he senses has the potential to give him problems; he enlists the help of Bernard to help get her out of the apartment. 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. Bernard tries to bond with Captain Czynencko, but she orders him out of her office. When Damon tells the Captain that he's taking Ally out to "pump her for information," she reminds him that this is an important case, and he better not blow it. When Damon goes for the bust, it's a washout; everyone's got a badge: Amy (minus the accent) is FBI, her boss who's Damon's target is Secret Service and there's even a D.E.A. guy on the scene; they're all cops. Ally and Damon are out on a real date the next night and are totally bored until they both pick up their fake Jamaican accents and the sparks begin to fly again.

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, so she gives up and leaves the place. The Captain says she's adopted an open-door policy, and everyone should bring their problems to her. Damon's neighbors down the hall are moving, and Damon realizes that a perfect way to get rid of Bernard is to have him move into their apartment; it's a hard sell and takes a while, but Bernard eventually accepts the idea. Damon adopts a number of disguises and successfully discourages several other perspective tenants. Damon waits for Tracy outside the newspaper building and offers her another chance to interview him, but she says he's clearly a selfish, troubled man and she wants no part of him. Bernard and Damon team up to scare off the two final apartment hunters, and Damon assures Bernard the place is about to be his. Damon goes to the Captain to share his problem with Tracy, but the Captain spends their time together talking about herself. And when Tracy tells Damon she's looking for an apartment, he encourages her to rent the available unit without a second thought for Bernard. Bernard's upset that Damon has given away "his" apartment, but he has the last laugh when he and Tracy become roommates.

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. Damon begs Bernard to help him, but Bernard says it's not going to happen with Tracy, so Damon might as well give up. Damon finally convinces Tracy to go to dinner but just as friends, but when it's time to go she brings Bernard along. During dinner Tracy tells Bernard, who's been making a point of showing her his sensitive side, that she wishes she had a man like him; Damon says that's ridiculous, but Tracy says that Damon has no idea what women want. Damon tells her that when men do what women say they want, the women tell their girlfriends that the guy's too soft. Tracy disagrees and says that Damon's a caveman. Damon says that women try to bring out another side in men, but there is no other side. What you see is what you get. But a couple of nights later Damon admits to Tracy he may have been overstating it a bit.

There's money missing from a gambling bust, and Internal Affairs suspects the Captain, Damon and his fellow detectives. Damon signs for a package while Tracy's away, but before he can give it to her, he and Bernard drop the box and break the one-of-a-kind Venetian glass vase inside. When she asks about her package, they both claim not to have seen it. Everyone's nervous about being questioned by Internal Affairs, but all are quickly cleared except the Captain. Damon tries to palm off a substitute vase on Tracy, but ends up confessing. He offers to make her dinner as an apology. Damon tells Bernard that he (Damon) needs to learn how to cook immediately and moments later loses his eyebrows when his gas oven explodes. Damon helps the Captain, who's very drunk, steal some information to help bring down a crooked judge and clear her name. Damon and Tracy have an incredibly romantic evening at his place that ends on a completely unexpected note. But Damon receives a letter from Tracy saying that her application for the Peace Corps has been accepted; she's giving up her apartment, so Bernard will have to move back in with Damon.

Bernard's depressed, he tells Damon, because he's a failure at everything: he's single, a security guard and sleeps on his brother's couch. Bernard says he should take the police exam, but Damon reminds him he's failed five times. Furthermore, every time Damon tries to help Bernard, Bernard wants to do it his way. Bernard says he'll train himself; he doesn't need Damon's help. At headquarters, the Captain is after Fontaine because he has too many unsolved cases. Damon senses that something else is wrong, and the Captain tells him that her ex-husband has just gotten married and wants her to have dinner with him and his new bride. Damon gives her a pep talk and agrees to be her dinner date. Bernard's trying to prepare for his police exam, but he clearly has no idea what he's doing. Damon says he's sure to fail the test, and Bernard grudgingly confesses that he does need some help from Damon. Damon subjects Bernard to rigorous physical training and role-playing exercises until he begs for mercy. The night before Bernard's test, Damon says he has to leave for his "date" with the Captain, but Bernard begs him not to go. The Captain is upset when Fontaine shows up for dinner in Damon's place, but Fontaine stands up to her ex-husband, and, by the end of the evening, has gotten quite romantic. Bernard learns he's passed the written exam and gets into the academy. When he's asked how he's respond in a crisis situation, he freezes up, and it looks like all is lost until Damon manufactures a "crisis" and everyone gets to see Bernard behave like a pro.

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. The woman, Carla, comes in to meet Damon who is introduced as Bernard. Carla says she understands he's a security guard. Damon's irritated, but he gets really upset when he realizes he'll be sleeping on the couch. Bernard and Damon give Carla a tour of the squad room. Carla can't understand why everyone seems to know Damon and not Bernard. The Captain tells everyone that they have to be more diligent about recycling and proceeds to make a speech on the subject. Back at the apartment Bernard begs Damon to allow him to keep up the charade for just one more night; very reluctantly Damon agrees, puts on Bernard's uniform and goes out to be a security guard for a night. Damon comes home after a very frustrating evening and finds Bernard, bald, dressed in his clothes, wearing his earring. He's even wearing Damon's underwear, but it's the last straw when he calls Damon "Bernard" when Carla's not even around. Damon demands that he tell Carla the truth; he wants his life back, but Bernard says he's not done with it yet. They go to the bank where Carla works so Bernard can make his confession, and someone tries to hold up the bank while they're there. Damon gets the situation under control, but Bernard helps out and considers himself a hero. When Bernard confesses to Carla, she says she has a tiny confession herself; her name used to be Carl.

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; he tells Bernard that he's as good an actor as Woodson. Damon helps the Captain convince Bernard to be her partner in a ballroom dance competition. Damon does his best to educate Woody, who's being a royal pain, that police work is serious business. But when Woody violates police procedure and screws up the bust at the antique shop, the press are on hand to see Woody drag Damon out of the shop and report that Woody saved the day. Damon's furious, but Woody manages to win him over by offering to get him a job on his TV series. And when Bernard convinces the Captain that she should stop trying to lead, they easily win the dance competition.

Stacy's frustrated that when she and Damon work together he always takes the lead; she complains to the Captain that Damon treats her like a rookie, but the Captain's too busy trying to get a date with the delivery guy to pay much attention. Damon tells the police shrink that the trouble between him and Stacy is sexual tension, but Stacy says it's that Damon's a control freak. Stacy and Damon are working on a fake designer clothing scam, and Damon finds out that Jimmy's the one supplying clothes to the guy they're trying to nail. Bernard meets a Chicago Bulls cheerleader while he's working his security job; Damon makes a dinner date with her, and she brings a friend for Bernard, but things go badly and the women leave the guys at the restaurant. And 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. Billy's upset with Damon even though the bullet just went into his shoe, until his co-workers assure him that being shot in the line of duty is great for his credibility. Bernard's positive that his estranged wife Janice is having an affair, but Damon promises to prove him wrong. When Stacy tells Damon that Janice will never confide in anyone but another woman, Damon puts on drag and "introduces himself" to Janice at a male strip club where she's spending the evening with some friends. In the women's restroom with Janice, Damon encounters Bernard, also in drag but having forgotten to shave his mustache. Janice confesses to Damon that she's having an affair with someone at the club, and both Damon and Bernard assume it's Tom, the club's owner and a stripper, who also happens to be a dwarf. Bernard's devastated that Janice would have an affair with a white guy and is determined to prove to Janice that Tom's being unfaithful to her. He convinces Damon to put on drag yet again and seduce Tom while he tapes their tryst. But when Janice is presented with the evidence, she laughs; she's having an affair with Jerry, another dancer at the club, and besides, her problems with Bernard go deeper than her casual affair or his affair (the reason why he's currently sleeping on Damon's couch). He's a good father but not a good husband. And Damon and Billy succeed in nailing the Mafia guys who have agreed to sell guns to them.

Damon and Stacy go undercover in a nursing home and nail some orderlies for abuse and theft. Bernard is fast-talked by Sammy, the neighborhood con man, and loses half of the rent money. Damon says they're going to scam the scammer and get the money back. 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. Billy helps Damon and Bernard as they try to scam Sammy, but they're unsuccessful and this time Sammy manages to relieve Bernard of his watch. Damon and the Captain have staked out a street fair where they observe money changing hands between a judge and the deputy chief of police; they step in and make an arrest, and the Captain's name is finally cleared. And Damon and Bernard get the rent money back by running a lottery ticket scam on Sammy.

Damon goes to a sporting goods store to buy some athletic shoes, but he ends up buying a lot of camping equipment he doesn't want so he can 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, and Elvin manages to abuse, insult and swindle all Billy's co-workers almost immediately. Damon persuades a very reluctant Bernard to come along on the camping trip by promising that two of Monique's beautiful girlfriends will also be going. At the campsite, Damon and Bernard prove to be total greenhorns: they can't put their tent together, have no idea how to build a fire and get a little jumpy about spending the night in the woods. Damon and Monique go off by themselves in the woods and soon encounter some redneck hunters. Damon tells Monique to run and they take off. He admits to Monique that he hates camping and they have a brief romantic moment. Back at the precinct, the Captain tells Billy that she wants Elvin out of there; an indignant Billy starts to defend him until he realizes that Elvin has stolen his wallet.