Crew haircut, thick glasses and thick figure - that’s Drew Carey, an assistant director of personnel in a Cleveland department store. Frustrated with his job he can always count on his friends.
1 | Revenge of the Doormat |
| The second return of Nikki Fifer (Kate Walsh).Drew struggles to find a job since Winfred-Louder went bankrupt. Lewis and Oswald take him to a strip club where they run into an old high school friend, Kelly. Drew goes to Never Ending Store and gets a job, though he has no clue what it entails, and Kelly shows a talent for waitressing. Finally, Kate drops by with a bombshell. |
2 | Kate’s Wedding |
| Kate introduces the gang to Kirk, a fighter pilot, whom she is about to marry. The guys try to find some dirt on Kirk so they can stop the wedding, but it’s too late. After the wedding, the guys share a melancholic moment. The final appearance of Kate O’Brien (Christa Miller). |
3 | Eyes Wide Open |
| Guest starring Kate Walsh as Nikki Fifer. Drew starts having bad dreams about Kate and begs Lewis and Oswald not to leave him alone. In a bid to help him, they decide to cheer Nicki up by taking her out so she’ll move out of his house. Now over Kate, Drew decides to set a date to get married. |
4 | Drew and the Life-Size Jim Thome Cut-Out |
| Kellie attempts to be part of the gang, but Oswald and Lewis are not impressed after she breaks down to their personal insults. Drew wants to give her a second chance so they take her out for a night. In an effort to show she is as wild and crazy as them, she steals a cardboard cut-out of Jim Thome, but when the police get involved she panics. |
5 | Hickory Dickory...Double Date |
| Oswald feels incredibly guilty after hitting his mother in the face with a bowling ball, so he hires someone to come to his house and beat him up. Meanwhile, he tells Drew a secret about Kelly. |
6 | Mama Told Me I Should Come |
| Drew’s new girlfriend has a queer habit that throws him off but his mom warns him of being too picky. Oswald’s sudden psychic powers cause Mimi and Lewis to bet on the race track based on his prediction. |
7 | Family Affair |
| The gang are planning to see a play, but after Drew gets home late and Steve says he has other plans with Mimi, they decide to see a movie instead. While there, Steve narrowly avoids being spotted by the gang with another woman. |
8 | Chemistry Schmemistry |
| Lewis causes a scene at a wedding where Drew is checking out music for his own ceremony. Later, his girlfriend, Robin, proposes to him very early on in their relationship; Drew discusses it with the others who all offer different opinions. |
9 | The Dawn Patrol |
| Oswald and Kelly have differing opinions on Drew’s decision to dump his girlfriend, Robin, so he can date Dawn whom he met on the bus, but then they both agree it was a bad idea when it turns out Dawn lets her ex-boyfriends hang around. |
10 | Drew’s Girl Friday |
| Mimi throws Steve out of their home so he stays with Lewis and Oswald, who invite Mimi over to patch things up, ending up in a huge fight between Mimi and Steve. |
11 | Drew Tries Hot Salsa |
| Drew joins a Salsa class to prep up his dance moves before his wedding. Guest star:Roselyn Sanchez as Maria. When Drew reveals he has feelings for Kelly to Lewis and Oswald, they advise him to bottle them up lest it may ruin his friendship with her. Later when Drew is about to confess to Kellie, they are interrupted by Kellie’s ex-husband, Daryl. |
12 | The Man in the Iron Chair |
| Drew tries to keep Kellie away from Daryl, who is confined to a wheelchair after falling off Kellie’s mom’s roof. However, he ends up looking as though as he is trying to hurt Daryl, and pushes the two closer together. Drew later confesses his feelings to Kellie, but she no longer seems interested. Meanwhile, Lewis plans to build an underwater city but continually fails to invite women to it. |
13 | Drew Takes a Guilt Trip |
| After Oswald fails his nursing school exam, Drew feels bad and helps him get a job at the web site. Oswald finds a way to nearly destroy the entire business and ends up being reassigned to a job that he is sort of familiar with - delivering packages. |
14 | Blecch Sunday |
| Drew lands a job in a commercial for Never Ending Store that will be broadcast live during the Super Bowl; however, he is reluctant to take it given his bad experiences in front of a camera. Lewis and Oswald keep him refreshed to stop him from passing out, but end up severely overstuffing him with snacks. |
15 | Turkeyspotting |
| Larry encourages Drew to lose weight before attending one of his singles mixers. Drew tries a little too hard by giving up food altogether, but his crash diet has some unintended side effects - temporary blackouts and hallucinations. |
16 | Suddenly No Summer |
| Drew tries to improve his standing at work by taking a computer course over the summer. The gang tempts him into blowing it off to take a trip to Florida. Drew is wracked with guilt and his vacation, not surprisingly, turns out to be a wreck. |
17 | What’s Love Got to Do With It? |
| The gang takes part in a karaoke contest. Drew tries to coach Kellie before her performance, but she gets so tired of his constant interference that she dumps him. Drew winds up having to take the stage with an 11-year-old girl as his partner. |
18 | Two Girls for Every Boy |
| The boys meet a priest in the bar and Drew gets a date with his daughter Elaine, who he finds out is a lesbian. Drew manages to set up a threesome with Elaine and his new date Teri, but after he falls asleep due to an overdose of cold medicine, they make off with each other. |
19 | Two Days of the Condo |
| Oswald and Lewis inform Drew of an offer of a free TV to newly married couples who stay at a condo, so he asks Kellie to pretend to be his wife for the weekend. But at the condo, things turn amiss when the condo manager repeatedly hits on Kellie and Drew knocks hims out. |
20 | Lewis You Can Drive My Car |
| Drew gives Lewis his Christmas bonus, a used Rolls Royce. However, the flashy car causes Lewis to undergo a strange personality transformation, and he can no longer be bothered to hang out with his longtime friends. |
21 | A Speedy Recovery |
| Drew finds an unexpected romance after he and Speedy get involved with an animal therapy program at a hospital. He agrees to loan Speedy to a dying woman, and sufficiently impresses the woman’s granddaughter. He finds the relationship may not be worth it when he learns that he may never see Speedy again. |
22 | A Means to an End |
| Oswald and Lewis seek revenge against Drew after they discover that he gave away their Christmas gifts–handmade mugs–to a thrift store. Drew winds up getting an unscheduled colonoscopy from a Russian veterinarian. |
23 | Drew Answers the Belle |
| Oswald and Lewis put Drew’s picture and phone number on Buzz Beer bottles in the hopes of landing him a wife. Much to everyone’s surprise, a southern belle named Lily responds to the campaign. Drew travels to Louisiana to meet the woman. They hit it off, and Drew believes he may have finally found his match. |
24 | What Screams May Come |
| Drew is left bruised and battered as Lily suffers from night terrors. He grows tired of the beatings, but is afraid to talk to her about her problem because he believes she would leave him. |
25 | Love is in the Air |
| Drew decides to propose to Lily. Mimi hopes to secure Gus’s admission into an exclusive prep school by setting up Kellie with the school’s headmaster. |
26 | The Bataan Wedding March |
| As Drew prepares to marry Lily, his mother Beulah realizes that Kellie has strong feelings for Drew and believes Drew feels the same way about Kellie. Drew and Lily go through with the wedding, but the union proves to be a brief one when they realize that they really are not right for each other. Drew winds up sharing a dance with Kellie. |