Drew catches the eye of an attractive stranger at the Warsaw. The woman, Bonnie, agrees to come back to his house to see his brewery. After she learns that he does not have a permit, she reveals that she is a zoning inspector and says that she must report him. Mimi (for a fee) suggests a way that Drew might get out of the situation. She says that the gang could organize a party and sell maps to the location, then give away the appropriate amount of beer. Bonnie comes to Winfred-Louder to apologize to Drew, and agrees to attend his party. She brings a policewoman friend to the gathering. Unfortunately, she threatens to arrest Drew and his friends for soliciting to sell alcohol unless they shut down the party and return everyone's money. Bonnie and Drew sleep together. She feels bad about causing him so many problems. She recommends that he get signatures on a petition and appear before the city council to request a change in the zoning laws for his neighborhood. The council h
Role: Chuck
Drew, Lewis and Oswald learn that their high school band teacher, Ms. Blankenship, has died. Drew seems to take the news especially hard. He organizes the band to put together one last performance for her, and becomes furious whenever anyone insults Ms. Blankenship. His friends ask for an explanation, and Drew reveals that he lost his virginity to her. He considers the experience to be special. However, he soon learns that the teacher regularly seduced her male pupils. Drew receives another shock when Kate and Oswald confess that they slept together once in high school. Drew feels like a fool because he was unaware of these secrets. Kate tries to cheer him up by proposing a secret of their own. She declares that they should get married if they are both still single by a certain age (which Drew keeps trying to lower).
Role: Chuck
Kate begins dating Jack, a guy that she met at the Warsaw. He interviews for a job at the store, and Drew is disturbed to learn that he thinks he is the devil. He has even taken out credit cards under the name ""The Devil."" Kate is certain that this is a joke, but soon discovers otherwise. When she tries to dump Jack, he claims that she has sold him her soul. Drew puts his own soul on the line and challenges Jack to a game of pool, but it doesn't go very well. Kate confronts Jack and says that he claims to be the devil because he is afraid that women will dump him if he acts like himself. He mocks her, so Drew prepares to beat him up. However, Jack loses interest when he learns that Kate lied about being a virgin. He leaves in disgust. Wick orders all of the staff to wear costumes for Halloween. Drew dresses as Mimi, who is outraged when he wears an outfit that she had already purchased.
Role: Chuck
Wick orders Mimi to begin wearing less make-up and more conservative clothing, as he doesn't want her representing him with her current appearance. When she refuses, Wick banishes her to the archives in the sub-basement. She tries to get revenge by wreaking havoc throughout the store. When Drew accidentally spills beer on a large man at the Warsaw, another man saves him from a fight. He turns out to be Simon, a bully who tormented the gang throughout high school. He apologizes for his actions and seems to have changed his ways. Simon is out of work, so Drew hires him as Wick's new assistant. Simon soon begins pushing everyone around, and even Wick becomes terrified of him. Wick decides to bring back Mimi, regardless of her appearance. He is too afraid to fire Simon, and leaves the task to Drew. Lewis, Oswald and Kate encourage Drew to stand up to Simon, claiming that bullies are really cowards at heart. Although Simon beats him up, Drew manages to fire him. Mimi doesn't wan
Role: Chuck
The Drew Carey Show - We'll Remember Always, Evaluation Day
Drew again finds his work coming between him and Lisa, when his negative evaluation of her job performance causes her to reevaluate their relationship.
Role: Chuck
Stagnated in his job, Drew takes the bull by the horns and convinces the board to use animal mascots for the store. But things turn beastly for Drew when the creatures get loose.
Role: Chuck
Lisa, Kate and Mimi are candidates to head the store's personal-services department, and Drew has trouble deciding among them.
Role: Chuck
Drew decides to ask out his party-animal hairdresser after Lisa cuts him loose to start dating other people.
Role: Chuck
Drew agrees to show Mr. Bell's spoiled nephew the ropes at work, but he's soon trying to give the upstart enough rope to hang himself.
Role: Chuck
After hiring a criminally insane employee, Drew has to fire him without creating any bad blood--or losing any good blood.
Role: Chuck
Drew and his buddies welcome back an old high-school friend, but Kate's up in arms about the "new guy" horning in on her territory.
Role: Chuck
The Drew Carey Show - No Two Things in Nature are Exactly Alike
Drew sends out a memo limiting employees' phone usage at work, but his attempt at levity--a risqué cartoon attached to the note--isn't well received by everybody.
Role: Chuck