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- OverviewSep 23, 1998-May 26, 199927 episodesEpisodes27. Brotherhood of Man May 26, 1999
- Drew takes initiative to save his co-workers' jobs when the owners threaten to close the store.
- 26. Up on the Roof May 19, 1999
- Sharon botches a roof job Drew urged her to take; guest Adrienne Barbeau.
- 25. Do the Hustle May 12, 1999
- Drew and Mimi become partners at hustling money from unsuspecting bowlers.
- 24. Good Vibrations May 5, 1999
- Sharon's practical joke short-circuits Drew's trip to a retail convention.
- 23. She's Gotta Have It Apr 7, 1999
- Drew gets involved with his handywoman; Wick finds a new favorite employee.
- 22. What's Wrong With This Episode II Mar 31, 1999
- A family friend's death reveals old secrets as Drew's folks near an anniversary.
- 21. Steve and Mimi Mar 24, 1999
- Drew's brother (John Carroll Lynch) becomes romantically involved with Mimi.
- 20. DrugCo Mar 3, 1999
- Drew sends his dog to Lewis' employer for experimental treatment; guest Charles Nelson Reilly.
- 19. Tracy Bowl Feb 24, 1999
- The guys' competition for Tracy reaches its peak, and she must make a decision.
- 18. Boy Party/Girl Party Feb 17, 1999
- Drew has a pajama party for his buddies so he can be alone with Tracy (Diane Farr).
- 17. Three Guys, a Girl and a B-Story Feb 10, 1999
- Courting competition begins when Drew, Oswald and Lewis each ask the same girl out.
- 16. Rats, Kate's Dating a Wrestler Jan 27, 1999
- A pro wrestler the gang hired to endorse Buzz Beer starts dating Kate.
- 15. A House Reunited Jan 13, 1999
- Drew asks Celia to move in with him when the company returns his house.
- 14. A House Divided Jan 6, 1999
- Drew says no when Winfred-Louder tries to buy the land on which Drew's house sits.
- 13. Drew's Holiday Punch Dec 16, 1998
- Drew's relationship with Celia moves smoothly until both of their families drop by unexpectedly.
- 12. Drew Dates a Senior Dec 9, 1998
- Drew is drawn to a mature woman (Shirley Jones) in his night-school class.
- 11. Kate's Family Nov 25, 1998
- Kate's maternal side shows when she house-sits and baby-sits for Drew's neighbor.
- 10. Drew's Dance Party Special Nov 18, 1998
- Clip show featuring dance numbers from "The Drew Carey Show.".
- 9. The High Road to China Nov 18, 1998
- When Mimi strands Drew in China he has neither passport nor money.
- 8. Drew's New Car Nov 11, 1998
- Oswald uses his breast implant money to surprise Drew with a new car.
- 7. Nicki's Wedding Nov 4, 1998
- At Nicki's wedding, Drew humiliates himself trying to impress her.
- 6. Cain and Mabel Oct 28, 1998
- Drew defends his transvestite brother.
- 5. Sexual Perversity in Cleveland Oct 21, 1998
- Drew and Mimi get intimate; Oswald gets temporary breast implants.
- 4. Drew Between a Rock and a Hard Place Oct 14, 1998
- Larry ruins the health plan when Mrs. Louder gives him authority to run the store.
- 3. Golden Boy Oct 7, 1998
- Drew learns who needs rehab when Mr. Wick institutes a drug-testing policy.
- 2. In Ramada Da Vida Sep 30, 1998
- Drew holds auditions to resurrect his band after jamming at the Ramada.
- 1. Drew and the Conspiracy Sep 23, 1998
- Drew learns a trio of co-workers conspires to make him miserable.