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The Best Episodes of The Drew Carey Show Season 5

Every episode of The Drew Carey Show Season 5 ranked from best to worst. Discover the Best Episodes of The Drew Carey Show Season 5!

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Episode Rankings

  1. #1 Fan Favorite
    The Drew Carey Show Season 5 Episode 21 - Oswald's Son
    7.6/10(98 votes)

    S5:E21

    A 21-year-old man claims to be Oswald's son, the result of a fling at a summer tap dance camp. However, the man bears a striking resemblance to Lewis. Lewis admits to Drew and Kate that he also slept with the girl. He believes that he must be the father, but Oswald argues that Robert actually looks like his mother. The guys arrange for separate outings with Robert, but begin bickering about ""custody"" issues. They finally decide to take a DNA test to find out which of them is the real father. Robert reveals that he is married and has a child of his own, and finally sought out his father because the baby doesn't have a grandpa. He is perfectly happy to have Lewis and Oswald share father/grandfather duties, so they decide to save their friendship by tearing up the results of the paternity test. Meanwhile, Drew's decision to allow the employees to put together the store newsletter proves disastrous.

    Director:Bob Koherr
    Writer:Mitch Hunter

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  2. The Drew Carey Show Season 5 Episode 26 - A Very Special Drew
    7.6/10(107 votes)

    S5:E26

    In a facetious attempt at Emmy bait, the melodramatic storyline features the characters coping with illiteracy, kleptomania, obsessive compulsive disorder and a coma. Lewis, the only one unaffected, breaks the fourth wall with monologues lamenting his insensitivity.

    Director:Gerry Cohen
    Writer:Unknown

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  3. The Drew Carey Show Season 5 Episode 7 - Red, White and Drew
    7.4/10(90 votes)

    S5:E7

    Drew becomes obsessed with getting the city to repair a pothole in front of his house. He supports a ballot measure allocating money for street repairs. When the nearest polling place suffers a fire just before the election, Drew volunteers his house as a replacement. Lewis and Oswald give people beer in exchange for a vote for the measure. Drew arrives home from work to find everyone partying. Aware that he could get in hot water for serving alcohol at a polling place, he tries to break up the gathering. A college student puts out his cigarette in the ballot box and causes the ballots to catch on fire. Oswald and Lewis distract the polling inspector to keep him out while Drew and Kate have everyone re-vote to replace the damaged ballots. The measure is handily defeated in spite of the gang's efforts. Drew ends up trying to repair the pothole himself in the middle of a rainstorm. He eventually agrees with his friends' contention that he is trying to distract himself because h

    Director:Gerry Cohen
    Writer:Mitch Hunter

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  4. The Drew Carey Show Season 5 Episode 3 - Drew and the Gang Law
    7.3/10(97 votes)

    S5:E3

    Lewis and Oswald start a web site for Buzz Beer, buybuzzbeer.com. The site helps the business tremendously. Lewis and Oswald hand beer over to minors and are arrested in a sting operation. Drew and Kate are infuriated by their stupidity, as they all get hauled into court. The judge agrees that their gaffe was a simple mistake, and decides to let them go because they are first-time offenders. Unfortunately, Drew backs his car into a police car outside the courthouse. The trunk pops open to reveal all of the Y2K supplies--including a loaded gun. The judge rules that the foursome causes too much trouble together, and uses the provisions of a new anti-gang law to order them to stay apart forever. Oswald has to move back in with his mother, and gets his head stuck in the banister. Everyone becomes extremely bored and lonely. Drew decides to go ahead with plans to hold Kate's birthday party at the Warsaw. All the guests are supposed to be in costume (so that the gang can remain in

    Director:Gerry Cohen
    Writer:Unknown

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  5. The Drew Carey Show Season 5 Episode 18 - Drew Goes to Hell
    7.3/10(88 votes)

    S5:E18

    Mr. Soulard and the board ask Drew to help them hire a regional store manager for Winfred-Louder. Drew inquires about getting a promotion to director of personnel, which has been vacant for years. Mr. Wick asks Drew to recommend him for regional manager (even though he is not qualified), and promises to return the favor by helping him get Wick's old job. Drew is adamantly opposed to the idea, but Kate and Lewis suggest that he show some initiative for a change. Soulard lays off Drew's incredibly efficient new assistant, Malcolm; and tells Drew that he cannot be promoted because they have completely eliminated the position of director of personnel. Drew decides to go along with Wick's plan. Wick plays a dirty trick to take care of Johnson, Drew's main competition for store manager. Drew and the gang celebrate at Wick's hangout, a bar called Hell. After Johnson shows up and makes a scene, an indignant Kate, Lewis and Oswald criticize Drew's actions and storm out. Drew goes to wo

    Director:Gerry Cohen
    Writer:Unknown

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  6. The Drew Carey Show Season 5 Episode 20 - The Gang Stops Drinking
    7.3/10(94 votes)

    S5:E20

    Kate wears an ear piece so that Drew can talk her through an interview with a catering company. She gets the job, and serves the guys some leftovers from her first assignment. They become violently ill, and blame Kate's cooking. However, Steve forces Mimi to confess to lacing a cookie (which Drew believed was a gift from his bosses) with a drug that causes vomiting when ingested with alcohol. The gang cannot drink for two weeks until the drug passes through their systems. Drew and Kate cannot spend any time together because of their busy schedules. He asks her to move in with him, but she believes they are moving too fast. He eventually agrees, and blames his temporary lapse in judgment on the sobriety. Lewis and Oswald begin seeing a pair of recovering alcoholics. After the drug wears off, they must choose between their new girlfriends and alcohol.

    Director:Gerry Cohen
    Writer:Unknown

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  7. The Drew Carey Show Season 5 Episode 24 - Beer Ball
    7.3/10(83 votes)

    S5:E24

    After Mr. Wick refuses to let him on the company softball team, Drew decides to organize his own team and challenges Wick to a play-off. When Drew realizes Steve is playing for the other team, it stirs up an old rivalry with his brother.

    Director:Sam Simon
    Writer:Unknown

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  8. The Drew Carey Show Season 5 Episode 4 - Drew's Reunion
    7.2/10(101 votes)

    S5:E4

    The gang prepares for its high school reunion. Kate plans to spend all of her time with Patrick, a geeky classmate who is now a wealthy computer software magnate. Lewis poses as Bo Derek's driver at the airport and somehow manages to convince her to be his date at the reunion (as long as he doesn't touch her). Oswald hooks up with his old barber shop quartet. The speaker humiliates Drew by pointing out that he is single, still has the same job, and lives in his parents' house. Drew is confused when Kelly, the former head cheerleader, suddenly expresses an interest in him. Bo Derek explains that he is attractive to women because he is a nice, stable guy. Patrick shows up late, so Drew invites everyone back to the house for beer so that Kate can spend more time with him. An attractive woman gets revenge on Oswald for calling her names in high school (when she was fat) and ignoring her after they made out in his basement. Drew discovers that Kelly leads an extremely dysfunctional

    Director:Gerry Cohen
    Writer:Brian Scully

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  9. The Drew Carey Show Season 5 Episode 11 - Steve and Mimi Get Married
    7.2/10(97 votes)

    S5:E11

    Beulah comes to town for Steve and Mimi's wedding. George is laid up with a back injury; but Drew and Steve's uncle, Alfred, makes the trip. Steve grows angry at Drew for making cracks about Mimi during a family dinner. Drew and Kate decide that they're not ready to tell his mom that they're dating, but she sees right through them. Steve discovers that Drew made a mistake on the order form for the wedding napkins; they have a typo that is insulting to Mimi. Steve accuses Drew of sabotaging the wedding, but forgets the dispute after they learn that Alfred has died. As a last request, Alfred asked to be buried in Drew's back yard, as he once lived in the house and was very happy there. Drew, Oswald and Lewis grow tired of digging the grave and decide to take a break. They get drunk and don't wake up until after Mimi has arrived for the wedding the next morning. The guys try to keep people away from the coffin, but Ed pulls away the cover during a magic trick. A distraught Steve

    Director:Sam Simon
    Writer:Unknown

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  10. The Drew Carey Show Season 5 Episode 14 - Kate Works for Drew
    7.2/10(86 votes)

    S5:E14

    Mr. Soulard tells Drew that his workload is too heavy, and allows him to hire an assistant. At the same time, Kate loses her job as Mrs. Louder's assistant. Drew claims that he doesn't know of any openings in the store, but Mimi mentions the assistant position so that Drew is forced to hire her. He realizes that it will be a disaster because of Kate's employment record. Kate's draconian methods prove very effective and force employees who had been ignoring Drew's paperwork requests to shape up. However, she quickly goes on a power trip and has the entire store at her mercy. Mr. Wick orders Drew to fire her. After Lewis totals Oswald's car, he tries to make it up to him by entering a contest at a local dealership. The group that stays inside a car the longest will win the vehicle. Lewis convinces Drew to put off firing Kate until after the weekend so that they can all take part in the contest. They develop a rivalry with a group of college kids in the next car. Kate learns sh

    Director:Gerry Cohen
    Writer:Unknown

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  11. The Drew Carey Show Season 5 Episode 17 - I Dishonestly Love You
    7.2/10(84 votes)

    S5:E17

    Kate feels extremely threatened when Drew receives a call from Wendy, his recently divorced college girlfriend. Drew assures her that she has no reason to worry, and agrees to have lunch with Wendy. She tells him that she returned to town in the hopes of escaping an obsessive ex-boyfriend. She hasn't worked for years, but hopes that Drew can give her a job at the store to help her get back on her feet. He hires Wendy as his assistant, and tries unsuccessfully to hide the truth from Kate. Kate gets jealous and storms off. While at the Warsaw, Drew receives a call from a panicked Wendy, who fears that her ex-boyfriend has tracked her down. Mimi overhears and suspects that the whole thing is a ploy to get Drew into bed. Drew begins to agree with her after he arrives at Wendy's apartment to find her in her underwear. She claims that her radiator is broken. Even after Wendy's ex-boyfriend shows up, Drew still believes it is a scam. He changes his mind after the guy punches him.

    Director:Gerry Cohen
    Writer:Brian Scully

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  12. The Drew Carey Show Season 5 Episode 5 - Drew's Physical
    7.1/10(90 votes)

    S5:E5

    Kate stuns Lewis by telling him that she is in love with Drew. She refuses to help Drew with a scheme to get a co-worker to go out with him, and becomes very jealous. Winfred-Louder employees must undergo physicals after the store switches insurance providers. Anyone who fails will lose health benefits. Oswald suggests that Drew have Lewis take the physical in his place. Their ruse is successful, but the exam also includes a psychological test. Lewis's answers cause everyone to believe that Drew is crazy. He takes advantage of this to get out of work, but is forced to go before the store therapist. Dr. Zinneman realizes that he didn't take the test, and says that Drew will just have to take a physical himself. However, he worries that Drew has low self-esteem, and recommends that he avoid relationships for a while. Kate must put her plans to share her feelings with Drew on hold after learning of the therapist's declaration.

    Director:Unknown
    Writer:Unknown

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  13. The Drew Carey Show Season 5 Episode 16 - Do Drew and Kate Have Sex?
    7.1/10(95 votes)

    S5:E16

    While Drew is shopping for a bed, Kate says she wants to have sex with him. The two decide to plan a "date" that weekend, but they end up ruining it for each other. They eventually have another "date," but when Drew walks back into the bedroom after putting on a condom, he trips over his dog Speedy and falls face first on the floor, spraining his penis in the process.

    Director:Sam Simon
    Writer:Unknown

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  14. The Drew Carey Show Season 5 Episode 22 - Mr. Wick Returns
    7.1/10(85 votes)

    S5:E22

    Mr. Wick returns from his retraining and begins duty in the mail room. He again vows revenge against Drew. On the morning of a major sale, a cowboy ambushes Drew in his back yard and ties him up. Drew fails to open the store on time, marking the first time in history that Winfred-Louder did not open on schedule. Soulard tells Drew that he is demoting him to his old job. Mimi pleads for a chance at the manager position. Soulard agrees to give her one day to prove that she can run the store. Mimi taunts Drew and reveals that she was the one who sent the cowboy--not Wick. Wick and Drew agree to join forces to keep Mimi from becoming permanent store manager. Wick suggests dipping the pickle she eats for lunch in grain alcohol to get her drunk. Their plan fails when the cowboy again jumps Drew. He arrives very late, and Mimi seems to be on the verge of winning the job. Steve brings by some remote-controlled vibrating panties that may help her get pregnant. She puts them on to w

    Director:Gerry Cohen
    Writer:Unknown

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  15. The Drew Carey Show Season 5 Episode 2 - Drew Goes to the Browns' Game
    7.0/10(98 votes)

    S5:E2

    Drew is disappointed when Sharon cannot spend much time with him because of her busy work schedule. Drew's screw-up prevents the gang from getting tickets to the first game by the new Cleveland Browns. Steve wins tickets from a radio station, but elects to take Mimi instead of Drew. Sharon tries to cheer him up by getting him a big screen TV for the game. However, she says that she cannot watch with him because she has to go out of town. Mimi feels that Sharon's gift smacks of guilt, and suggests that she is cheating on Drew. Sharon has left her purse behind, and Drew uncovers evidence that seems to prove Mimi right. Drew confronts Sharon, who seems to have a logical explanation. Lewis convinces the gang to hide out in portable restrooms and sneak into the stadium. They end up spending the night in porta-potties that are left outside the gates. Kate disracts the VIP gate guard, an old classmate who has the hots for her, so that everyone can sneak in. Drew is having a good ti

    Director:Gerry Cohen
    Writer:Unknown

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  16. The Drew Carey Show Season 5 Episode 9 - Drew Cam
    7.0/10(93 votes)

    S5:E9

    Winfred-Louder recruits Drew to promote products from his home live on the store's website. After receiving numerous E-mail complaints about Drew's boring life, the store decides that he should have a girlfriend on his ""show."" Kate eagerly accepts the job. After site visitors complain that the couple has no chemistry, Mr. Wick fires Kate and replaces her with a beautiful latina woman. Drew and Isabel draw a wildly favorable audience response, and get along well off camera. A jealous Kate storms off after Drew reveals plans to ask Isabel on a date. Drew and Oswald realize that Lewis knows why Kate has been acting strangely. They try to get him drunk to pry the truth from him. Kate goes to Drew's house to apologize, but again becomes territorial around Isabel. Isabel gets the idea and leaves Kate to talk with a still-clueless Drew. After he refuses to talk privately, Kate tells Drew that she loves him during the webcast. He is stunned, but ecstatically happy.

    Director:Sam Simon
    Writer:Unknown

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  17. The Drew Carey Show Season 5 Episode 12 - Drew and Kate's First Date
    7.0/10(102 votes)

    S5:E12

    For their first date, Drew takes Kate to the planetarium where they first met on a third grade class trip. They compare stories about wild experiences, and Kate recalls picking up a guy at the airport in nothing but a trenchcoat. Drew fears that Kate finds him boring after she falls asleep on the couch with her head on his shoulder during their date. He fears that she will dump him unless he does something exciting on their next date. Drew shows up wearing only a trenchcoat, but Kate doesn't realize that he isn't wearing anything else. She takes him somewhere as a surprise, and Drew thinks that she has something crazy in mind. She instead brings him to a Greek restaurant to dine with her visiting grandparents. Drew manages to hide the fact that he isn't wearing pants, until the restaurant staff carries him around on its shoulders as part of a traditional dance. Kate tells Drew that she fell asleep because she feels comfortable with him. She does not want to rush their relation

    Director:Gerry Cohen
    Writers:Jonathan Stark, Tracy Newman

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  18. The Drew Carey Show Season 5 Episode 15 - Mimi Moves In
    7.0/10(89 votes)

    S5:E15

    Steve and Mimi buy a trailer and plan a trip to Dollywood. Mr. Soulard orders Mimi to alter her appearance and remove all personal items from her desk. When she objects, he puts walls around her desk so that she can't be seen by visitors. Mimi refuses to stay in her office, and Mr. Soulard fires her for failing to answer her phone. She and Steve decide to leave with the trailer, and never plan to return. They announce their plans when they stop by Drew's house to pick up some of Steve's belongings. A jubilant Drew offers to take their truck to the gas station for a fill-up; but has it stolen when he goes inside for a pretzel. Mimi and Steve are left stranded in Drew's yard, and cannot get a new truck because Steve allowed their insurance to lapse. Drew grows tired of the couple's monopolization of his food and utilities, and sickened by the continuous rocking of the trailer. Kate finds an affordable trailer park, and Drew offers to pay the first six months' rent. Mimi angrily

    Director:Unknown
    Writer:Mitch Hunter

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  19. The Drew Carey Show Season 5 Episode 25 - Drew and Kate Boink
    7.0/10(85 votes)

    S5:E25

    Drew tells Oswald and Lewis the good news that his penis has healed. After meeting her ex-boyfriends at the Warsaw, Kate tells Drew that she fears he may meet the same fate. Drew assures her with a big ballad and later consummate their relationship. Meanwhile, Steve and Mimi announce that Mimi is pregnant.

    Director:Gerry Cohen
    Writer:Unknown

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  20. The Drew Carey Show Season 5 Episode 13 - Drew and the Racial Tension Play
    6.9/10(92 votes)

    S5:E13

    Winfred-Louder celebrates its centennial. Drew selects Arthur Crawford, a board member who has worked at the store since 1936, to speak at the festivities. He puts aside the speech Drew had written and begins making stereotypical remarks about other races and religions, as well as gays. All of the employees are outraged; they threaten to go on strike and sue the store. They soon turn on each other and begin making offensive comments about one another. Drew promises that he will either get Crawford to apologize or resign. Crawford refuses to cooperate, and the board just tells Drew to look through the store's handbook for a solution. The tension between employees results in a race riot in the cafeteria. Drew tries to calm everyone by following the handbook and putting on a play about stereotypes with Kate, Mimi, Chuck, Doreen and another woman. The play is really awful, and doesn't have any effect on anyone. When Drew returns to the board to explain, he discovers that the Dutc

    Director:Sam Simon
    Writer:Unknown

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  21. The Drew Carey Show Season 5 Episode 23 - Kate vs. Speedy
    6.9/10(92 votes)

    S5:E23

    Kate begins staying over at Drew's house so that they can spend some time together. She accuses him of spoiling Speedy, and tries to put a stop to this. Speedy begins to display hostility toward Kate. She becomes afraid of the dog, and forces Drew to tie him up outside. Oswald's supervisor comes along on his deliveries as he gives him an evaluation. Speedy bites the supervisor when he tries to untangle his leash. Drew blames Kate for Speedy's sudden change in behavior. Lewis recommends that Drew seek the advice of an animal psychologist from DrugCo. She quickly determines that Kate and Speedy are fighting for control of Drew, and gives him a squirt gun to use whenever they begin pushing him around. Kate admits that she has been too demanding. Steve has problems in the bedroom. He and Mimi must follow the same routine each time to increase her chances of pregnancy, and he feels too much pressure. Mimi forces a bewildered Mr. Wick to have a talk with him.

    Director:Ryan Stiles
    Writer:Unknown

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  22. The Drew Carey Show Season 5 Episode 1 - Y2K, You're Okay
    6.8/10(101 votes)

    S5:E1

    Drew and the others are convinced that the end of civilization is nigh and have Sharon build a bomb shelter for them, while Mimi has got a new Mini Mimi. Sharon is worried that Drew is in love with Kate.

    Director:Gerry Cohen
    Writers:Diane Burroughs, Joey Gutierrez

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  23. The Drew Carey Show Season 5 Episode 6 - Drew Tries to Kill Mimi
    6.8/10(100 votes)

    S5:E6

    Mimi tricks Drew into believing that an important executive waiting to speak with him is actually interviewing to be Winfred-Louder's janitor. After he makes a fool of himself (with comments that seem racist when taken out of context), he vows to kill Mimi. Later that day, a bee flies into Drew's car as he is driving out of the garage. While he is trying to get it out of his face, he loses control of the car and nearly hits Mimi. She believes that he was really trying to kill her, and has him arrested for attempted murder. Steve insists that Drew would never really try to kill Mimi, but she refuses to drop the charges. Kate annoys the detectives investigating the case by babbling about herself and her feelings for Drew instead of answering their questions. Mimi tries to convince the detectives that Drew wants her out of the way before the wedding. They plan to indict him and send him to prison. Steve feels that Mimi will realize that Drew is innocent if he proves that he doesn

    Director:Sam Simon
    Writer:Unknown

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  24. The Drew Carey Show Season 5 Episode 8 - Drew Live
    6.7/10(105 votes)

    S5:E8

    Steve objects to Mimi's plans for a wild bachelorette party at a strip club. They decide to hold their bachelor and bachelorette parties simultaneously at Drew's house. After Drew mentions that he might start dating again, Kate tells Lewis that she is going to make her move. Drew overhears her say that she is going to tell someone she loves him during the party, but doesn't know that she is talking about him. Drew plots to keep Kate away from the guy. He ignores her obvious attempts to talk to him (as well as Lewis's hints) and makes a complete fool of himself. They both decide not to confess their feelings yet.

    Director:Gerry Cohen
    Writer:Clay Graham

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  25. The Drew Carey Show Season 5 Episode 10 - Drew's Stomach Ache
    6.7/10(96 votes)

    S5:E10

    Kate and Drew prepare to go on their first date. He begins to experience severe stomach pains, which he assumes are the result of stress over Steve and Mimi's upcoming wedding. The pains grow so severe that he has to go to the hospital, and the doctor agrees that the cause is psychological. Kate discovers that Drew feels fine when the wedding is discussed, but cannot handle any mention of their date. She is crushed, and suggests that they back off for a while because she doesn't want to see him in pain. Lewis gives Drew some extra-strong pain pills from DrugCo. He dreams that he has a conversation with his stomach, who tells him that he is subconsciously making himself sick to avoid dating Kate because he is afraid of screwing up the relationship. He advises Drew to just relax. Drew goes to Kate's apartment the next morning. He kisses her and jubilantly announces that he doesn't feel like throwing up. Meanwhile, Mimi and Steve have an interview with her priest as one of the f

    Director:Gerry Cohen
    Writer:Unknown

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Season 5 Ratings Summary

"Oswald's Son" is the best rated episode of The Drew Carey Show season 5. It scored 7.6/10 from 98 votes. Directed by Bob Koherr and written by Mitch Hunter, it aired on March 29, 2000.