The BEST episodes of The Drew Carey Show season 4

Every episode of The Drew Carey Show season 4, ranked from best to worst by thousands of votes from fans of the show. The best episodes of The Drew Carey Show season 4!

This long-running sitcom stars comedian Drew Carey as a sort of blue-collar everyman. The show chronicles Drew's working life, the ups and downs of his romances and his strong relationship with his long-time friends Lewis, Oswald and Kate.

Last Updated: 11/8/2024Network: ABC (US)Status: Ended
star
7.63
52 votes

#1 - Golden Boy

Season 4 - Episode 3 - Aired 10/7/1998

Drew lets Darcy dye his hair blonde and grows a goatee so that he will look more like a musician. Larry discovers that someone has been doing cocaine in the men's room at Winfred-Louder. Wick orders Drew and Mimi to collect specimens from every employee for drug testing. Drew does not like invading everyone's privacy. After the men accuse him of being a narc, he throws out all the samples. Wick orders him to give his own sample. Drew refuses and brings in a drug-sniffing dog. Wick becomes furious and fires him. Drew goes into Wick's office and discovers that Wick is the one who is on drugs. He helps him get into rehab. Oswald and Lewis become jealous of Drew's musical success and try to talk him into letting them back into the band. Mimi ends her relationship with Ron after she receives an unpleasant visit from his wife.

Directors: Gerry Cohen
Watch Now:Amazon
star
7.57
46 votes

#2 - The High Road to China

Season 4 - Episode 9 - Aired 11/18/1998

Drew pulls off an elaborate practical joke against Mimi and boasts that she will never be able to top it. A few days later, he wakes up to find himself on the Great Wall of China with no money or passport. Mimi has left a tape recording in his pocket in which she taunts him. Drew gets a ride into a small town, where a young woman who speaks English offers him shelter. She gets him a job helping her family sell chickens so that he can eventually afford bus fare to Beijing and go to the U.S. embassy. Kate, Lewis and Oswald grow concerned after they discover that Drew never made his scheduled business trip to Winnipeg. Mimi brags about sending Drew to China. She explains that she had her father's secretary drug Drew and put him on a courier flight. The gang has no idea what to do to help him. Ming finally agrees to drive Drew to Beijing, but the embassy is closed for Thanksgiving. He tries to make enough money to get himself a hotel room by putting on a sock puppet show, but onl

Directors: Gerry Cohen
Watch Now:Amazon
star
7.44
77 votes

#3 - Drew and the Conspiracy

Season 4 - Episode 1 - Aired 9/23/1998

Drew suffers a constant series of mishaps at work and begins to suspect that someone is out to get him.

Directors: Gerry Cohen
Watch Now:Amazon
star
7.42
72 votes

#4 - Sexual Perversity in Cleveland

Season 4 - Episode 5 - Aired 10/21/1998

Darcy breaks up with Drew after he admits that he is not a full-time musician. He starts spending a lot of time at his computer, and begins a steamy on-line affair with an anonymous woman. He becomes concerned after learning that his chat room girlfriend works at a department store and has a large collection of troll dolls. When he confirms that it is Mimi, Drew begins showering compulsively. He feels extremely awkward when he and Mimi run into each other while visiting Wick in rehab. Mimi does not realize that she was involved with Drew, and is angry that she hasn't heard from her online man for a while. Drew gets really drunk and writes her a kiss-off note in which he claims to be Bill Clinton. Meanwhile, Oswald grows concerned about his mother's financial status after her birthday check to him bounces. He learns that her business partner deserted her, and that she may lose her beauty salon and house. Oswald follows Lewis's advice and agrees to test breast implants for DrugC

Directors: Gerry Cohen
Writer: Mike Larsen
star
7.35
107 votes

#5 - Drew Between the Rock and a Hard Place

Season 4 - Episode 4 - Aired 10/14/1998

Mrs. Louder asks Drew to fill in as store manager while Mr. Wick is in rehab. He refuses, as he is having a great time with his band and doesn't want to deal with all the hassles of the job. Mrs. Louder reluctantly gives the job to Larry. A man approaches Drew and offers the Horndogs the chance to go on a tour of all the Ramadas in Ohio. He decides to accept the offer and quit his job. Kate doesn't think this is a good idea, as she ended up working as a "booze wench" at the Ramada after quitting Winfred-Louder. A plastered Wick shows up at Drew's show and says that he was kicked out of rehab because of a change in his health insurance. Drew discovers that Larry changed the employee coverage to an HMO so that he could spend $100,000 on a Jacobs Field skybox for Mrs. Louder. Drew is upset because he had fought hard to get good coverage for everyone. The employees plead with him to go through the budget and find some way to make up the lost money and get their health plan back.

Directors: Sam Simon
Writer: Richard Day
Watch Now:Amazon
star
7.30
50 votes

#6 - In Ramada Da Vida

Season 4 - Episode 2 - Aired 9/30/1998

Drew entertains a group of investors from Vietnam who are considering opening a store in Hanoi. They have drinks at the Airport Ramada Inn. When the house band goes on break, Drew and the guys fulfill the investors' request for music by taking the stage for a song. The manager feels that they are better than the regular band and asks them to play for a week. Drew fears that this would be too much of a distraction and wants to focus on his new job. He changes his mind after a groupie hits on him in the parking lot. The guys audition guitar players, and hire a free-spirited guy named Ed. Kate becomes dissatisfied with her job and tries to get fired. Drew agrees to let her go, but promises to re-hire her if she can't find a better job in a week. She doesn't have any luck, but Drew backs out of the deal because he wants her to find the kind of happiness he now has with his band. Drew blows off a party at Mrs. Louder's house, and later skips work to fool around with Darcy. The ho

Directors: Gerry Cohen
Writer: Clay Graham
Watch Now:Amazon
star
7.21
67 votes

#7 - Drew's New Car

Season 4 - Episode 8 - Aired 11/11/1998

Drew must submit candidates for Winfred-Louder's employee of the year, who will win a trip to Hawaii. A legitimate employee may win for the first time in history, as all of the Louders have (apparently) already received the award. Mimi tricks Drew into including her name on the list. She attends sobriety events with Mr. Wick in the hopes of getting his vote. Oswald receives another $10,000 by posing for the DrugCo calendar before his implants are removed. He decides to use the money from his "man boobs" to repay his debts to his friends. Drew's car rolls down a hill and gets wrecked. Oswald and Kate decide that they should pool all of the money and buy Drew a VW Bug. Lewis doesn't want to cooperate, but has no choice because Oswald hadn't actually given him his money yet. Drew is touched, but elects to sell the car and use the money to help his friends. Kate, Lewis and Oswald take offense to his actions. Drew tries desperately to get the car back from Mimi. She will only ag

Writer: Terry Mulroy
Watch Now:Amazon
star
7.19
103 votes

#8 - Boy Party / Girl Party

Season 4 - Episode 18 - Aired 2/17/1999

Drew has trouble getting another date with Tracy because Lewis and Oswald are keeping her booked. He meets one of Winfred-Louder's catalog models, who complains that she and her model friends haven't been invited to any parties while in Cleveland. Drew follows Kate's suggestion by organizing a slumber party at his house for the models. Drew plans to sneak out for a date with Tracy during the party. Unfortunately, a blizzard keeps the models away and prevents Drew from going on the date. Lewis and Oswald learn of his plans and vow revenge. They suggest that the guys at the party learn swing dancing to impress the ladies, and proceed to injure Drew as many times as possible. They decide to set aside all rules or attempts to act gentlemanly as they pursue Tracy. Mimi holds a women in business seminar, where Kate sucks up to Mrs. Louder to get her job back. Steve also attends, explaining that the fact that he dresses as a woman means that he faces the same disadvantages as women i

Directors: Sam Simon
Watch Now:Amazon
star
7.19
73 votes

#9 - Cain and Mabel

Season 4 - Episode 6 - Aired 10/28/1998

Steve comes to the Warsaw while dressed in drag. A man mistakes him for a woman and tries to buy him a drink. He gets angry when he learns the truth about Steve, and insults him. Drew stands up for his brother. Steve's transvestite friends begin frequenting the Warsaw as a show of solidarity. They dance and play loud music all of the time. Drew, Lewis and Kate become annoyed when other customers begin staying away, as this makes it even harder for any of them to find a date. Drew suggests that the bar get the female customers back by holding a ladies' night with half-price drinks. Steve is outraged when the bartender only gives the discount to actual women, not the cross-dressers. Drew refuses to take his side. Steve accuses Drew of trying to force him out of the Warsaw because he is ashamed of him. Drew insists that he is actually upset because Steve is trying to take away his bar. He says that Steve has been stealing things that Drew liked since they were children. Steve

Directors: Gerry Cohen
Writer: Dan O'Keefe
Watch Now:Amazon
star
7.14
72 votes

#10 - Nicki's Wedding

Season 4 - Episode 7 - Aired 11/4/1998

Mimi runs into Nicki at the store's bridal registry. Nicki has to race upstairs to try to keep Mimi from telling Drew about her wedding plans; she had wanted to share the news herself. He claims that he is happy for her. Drew is surprised when Nicki sends him a wedding invitation. Kate, Lewis and Oswald insist that it is only a courtesy invitation and try to discourage him from attending. They plan to stay away as well, but Drew urges them to go to the wedding. Oswald is really excited because the wedding is on a boat. Drew goes on a date with a video store clerk, but suddenly decides to take her to the wedding. Nicki's parents cannot believe that he had the nerve to show up. Drew makes a complete fool of himself while trying to prove how mature he is. He actually manages to give a toast that isn't totally humilating, but throws out his back while trying to show up the groom on the dance floor. As Drew waits for the helicopter to lift him off the boat to take him to the hosp

Directors: Gerry Cohen
Watch Now:Amazon
Drew's Dance Party Special
star
7.11
35 votes

#11 - Drew's Dance Party Special

Season 4 - Episode 10 - Aired 11/18/1998

The gang learns that its favorite local radio station is going off the air. They decide to have a slumber party at Drew's house and request a bunch of songs. The station has so many requests that the lines are busy for hours. Oswald goes out for beer, but instead goes to the station and pays the D.J. to let him take over. He plays all of his friends' favorite songs.

Directors: Gerry Cohen
Writer: Clay Graham
Watch Now:Amazon
star
7.08
103 votes

#12 - Tracy Bowl

Season 4 - Episode 19 - Aired 2/24/1999

The guys vie for the right to take Tracy to a wedding. The winner will officially be in a relationship with her, as he would have to travel out of town with her and meet her family. Sports broadcasters Bob Costas, Lynn Swann and Kenny Mayne provide a running commentary during the competition. Drew and Oswald separately slip Lewis strawberries and put fish oil in the wine in order to trigger his allergies during a dinner date with Tracy. The combined effects cause his face to puff up. He requires medical attention, and Tracy freaks out. Drew feels guilty and suggests that he and Oswald sabotage their own chances with Tracy so that Lewis can get the girl for a change. Oswald agrees, and makes himself look bad by parking in a handicapped space. Drew does not go along with the bargain, and Tracy rejects Oswald. Oswald and Lewis are furious at Drew for stabbing them in the back. Drew rigs a fortune telling machine at the Warsaw to say bad things about him, and blames it on Lewis.

Directors: Sam Simon
star
6.92
105 votes

#13 - Three Guys, a Girl and a B-Story

Season 4 - Episode 17 - Aired 2/10/1999

Lewis meets a woman at a Babylon 5 convention and gets a date with her. Oswald gets a date with the same woman, Tracy, when he delivers a package to her house. It is an ice cream maker from Lewis, but Oswald doesn't know this because Lewis wrote his name and address in an alien language from Babylon 5. Drew meets Tracy when she complains to him about the store's reluctance to exchange the broken ice cream maker. He also gets a date with her. The guys are excited to have found possible girlfriends, and have no idea that they are dating the same woman. They seek advice from Kate on how to make a first date special. They follow her suggestions a little too literally and freak out Tracy by each following the same routine (paying everyone at the Warsaw to yell out his name when he enters, pulling out a pocket watch, and singing the Commodores' "Three Times a Lady"). The guys finally run into each other during Drew's date and realize what has happened. Tracy is mortified. Drew late

Directors: Gerry Cohen
Writer: Jody Paul
star
6.92
76 votes

#14 - A House Reunited

Season 4 - Episode 15 - Aired 1/13/1999

Celia returns from an out-of-town trip and learns about Drew's fight with Winfred-Louder. She offers her support. The store recruits Mimi to try to drive Drew out of the house. She points blinding lights at the house and constantly blasts "Panama" by Van Halen. Larry and Chuck later tell Drew that Winfred-Louder's investors gave up and backed out of the mall project. The store decides to rent all of the houses it had purchased to employees. After learning that Mimi continued to torment him for days after he had already won the battle, Drew gets revenge by tricking her into sending her outfits to a fake dry cleaner, who ruins them. Drew asks Celia to move in with him. Lewis, Oswald and Kate become creeped out by Drew's relationship with Celia, as they feel that they are acting like mother and son. The store's contractor reassembles Drew's house in an improper fashion, causing the kitchen to slope. Wick refuses to pay for the repairs, so Drew has to contact a lawyer. Drew and

Directors: Steve Zuckerman
star
6.88
76 votes

#15 - DrugCo

Season 4 - Episode 20 - Aired 3/3/1999

Lewis is a finalist for a promotion to head of the janitorial department at DrugCo. Oswald insists on keeping a tanning bed that Kate's uncle in Ireland recently sent them as a belated wedding present. Drew discovers that Speedy is losing his vision because of cataracts. Lewis gets him into an experimental treatment program at DrugCo, but he must stay on the premises for at least a week. Lewis gets the promotion. When he tries to ask his boss about Speedy's status, Mr. Hathaway denies ever seeing Speedy and warns Lewis not to ask questions. Lewis uses his new security clearance to sneak the gang into the building. While searching for Speedy, they encounter many strange things, such as an insect man using the bathroom and a a combination monkey/hippo. Drew finds a silver globe that causes epiphanies when touched, and theorizes that Oswald kept the tanning bed because he still harbors resentment toward Kate. Oswald holds the globe and realizes that he has a fear of abandonment.

Directors: Gerry Cohen
star
6.87
103 votes

#16 - Drew's Holiday Punch

Season 4 - Episode 13 - Aired 12/16/1998

Drew's parents arrive unexpectedly for Christmas. They assume that Celia is his maid, and he is reluctant to reveal the true nature of their relationship. Celia's son, Chip, shows up at her house in the middle of the night. He has come to visit for the holidays. When Drew comes downstairs in Celia's bathrobe and tries to make conversation, Chip punches him in the face. Drew's parents are horrified when he finally tells them that he and Celia are dating. Celia and Chip come over to Drew's house to have dinner with Drew's parents and Steve. It proves to be a disaster. Meanwhile, Lewis and Oswald agree to help Mimi with door-to-door Christmas tree sales after she fires an associate. Kate comes along to help supervise the guys. They make very few sales (aside from Wick buying two trees to get them to go away), and accumulate several fines.

Directors: Gerry Cohen
Writer: Mike Larsen
star
6.87
103 votes

#17 - A House Divided

Season 4 - Episode 14 - Aired 1/6/1999

A corporation tries to convince everyone in Drew's neighborhood to sell their houses to make way for a new mall. Drew is reluctant, but agrees to think it over. Mrs. Louder reveals that Winfred-Louder is behind the project. She and Mr. Wick try to sweet-talk Drew to get him to sell. He is interested in moving to lakefront property, but does not want to give up his family home. Mimi suggests that Winfred-Louder move the entire house, and Mrs. Louder agrees. Mimi later tells Drew that she has accessed Wick's E-mail and learned that the house will not be moved to the lake. Drew goes home and discovers that half of his house has been taken away, a week earlier than scheduled. Mrs. Louder and Wick claim that Drew's house was rejected by the lakeside property owners' association. They offer him another lot, which he accepts. Oswald, Kate and Lewis lodge a protest against the homeowners association, only to learn that Winfred-Louder never bought a lot in the area or submitted Drew's

star
6.86
74 votes

#18 - Do the Hustle

Season 4 - Episode 25 - Aired 5/12/1999

Steve and Sharon grow tired of Drew and Mimi's constant sniping. They suggest that the foursome go on a double date in the hopes that Drew and Mimi might finally agree to a truce. They constantly insult each other, and Steve and Sharon leave angrily after Mimi sets Drew's menu on fire. Mimi and Drew are left stranded, and have to walk to the bowling alley to call for rides. They decide to bowl while they wait, and end up hustling two doctors out of four-hundred dollars. Drew and Mimi agree to meet each night to continue their scam. They keep it a secret because they fear that Steve and Sharon would force them to go on more double dates if they knew they were getting along. Mimi gets in over her head when she accepts a two-thousand dollar bet from some men. It turns out that they are professional bowlers, hired by the doctors that Drew and Mimi beat in their first scam. Drew tries to flee, but Sharon and his friends show up before he can escape. Drew and Mimi compete very well

Directors: Sam Simon
Writer: Maria Espada
star
6.85
100 votes

#19 - Drew Dates a Senior

Season 4 - Episode 12 - Aired 12/9/1998

Drew decides to take night school classes to pursue a master's degree after a young man he was mentoring suddenly receives an executive position at Winfred-Louder. When his statistics professor recommends that the students find study partners, Drew pairs with Celia, a 62-year-old woman who is the only other "old person" in the class. They have a good time hanging out at Drew's house after a study session, and soon realize that they are attracted to each other. Celia stays the night, although they do not have sex. Drew's friends mock him after learning of the age difference, but he insists that he really likes Celia. He is puzzled when Celia ignores him in class and says that she doesn't want to see him anymore. Drew shows up at her favorite bingo parlor, and Celia explains that she dumped him because she thought he would eventually become embarrassed by her. Drew proves himself by taking over for the bingo caller and publicly announcing his feelings. Celia agrees to date him.

Directors: Gerry Cohen
star
6.85
72 votes

#20 - Steve and Mimi

Season 4 - Episode 21 - Aired 3/24/1999

Drew is forced to lay off a slew of workers as Winfred-Louder suffers a financial decline. Drew agrees to let Steve stay at his place after he becomes a victim of the cutbacks. As the gang is helping Steve move in, Mimi comes over with another list of people for Drew to fire. She is impressed with the way Steve looks out of drag, and they flirt. They set up a date, but Steve suggests that they keep it a secret from Drew. Mimi is disappointed when she arrives to find that Steve is wearing a dress, as she assumed that he dressed as a man on dates. They decide to just hang out and be friends. They get along very well, and a shocked Drew comes home to spy them kissing. He keeps his discovery to himself as he tries to deal with it, but later accidentally sees Steve and Mimi having sex in the kitchen. Drew and Mimi bicker and put Steve in the middle of their argument. Mimi ends up storming out. Steve and Mimi both grow extremely depressed. Drew feels bad for Steve and realizes th

Directors: Gerry Cohen
star
6.83
104 votes

#21 - She's Gotta Have It

Season 4 - Episode 23 - Aired 4/7/1999

A depressed Sharon shows up at the Warsaw after breaking up with her boyfriend. It is closing time, so Drew offers to let her come to his house for a beer. He promises to be a perfect gentleman, but she suddenly jumps him. Sharon leaves before Drew gets up, and acts weird when he calls her for a date. She begins showing up at the house frequently. She tells him that she is only interested in sex, and does not want another relationship. Drew begins to feel like a gigolo. Although Sharon is reluctant, he eventually persuades her to begin dating him. Meanwhile, a Winfred-Louder employee ingratiates himself with Wick by hanging around and never saying a word.

Directors: Tommy Thompson
star
6.82
74 votes

#22 - Rats, Kate's Dating a Wrestler

Season 4 - Episode 16 - Aired 1/27/1999

The Warsaw must temporarily close after it is taken over by super-intelligent rats from DrugCo, which escaped from a cage in Lewis's apartment. In order to keep Buzz Beer afloat in the meantime, the gang asks a popular pro wrestler to serve as spokesman. The company begins making a profit for the first time. Kate begins dating The Disciplinarian, much to Drew's chagrin. They get into an argument after Drew notes that all of her relationships end in disaster. The Disciplinarian, once devoted to his fitness routine, starts getting drunk all the time and missing public appearances. Drew warns Kate to cut him loose, while she feels that the gang is working him too hard. Kate nearly ruins The Disciplinarian's career when she takes him to Atlantic City, where he loses $20,000 and winds up naked in a fountain. He breaks up with her and denounces Buzz Beer. However, his comments actually lead to more business, as everyone wants to try the beer that could "kick The Disciplinarian's ass

Directors: Steve Zuckerman
star
6.81
99 votes

#23 - Good Vibrations

Season 4 - Episode 24 - Aired 5/5/1999

Drew is thrilled when he wins the opportunity to give a speech at a retailers' convention in Chicago. He engages in a practical joke war with Lewis and Oswald. The guys play a joke on Sharon, and she promises to get back at them. Drew gets stopped by airport security, which finds a vibrating marital aid in his bag. He is humiliated in front of all the representatives from other stores, and everyone makes jokes and laughs at him during his speech at the convention. Drew assumes that Mimi is responsible. He goes before the board to request her firing. However, Sharon actually staged the joke, with help from Kate and Lewis. She says that she just wanted to feel like one of the gang. Drew is upset with her for jeopardizing his professional reputation. They break up, but Sharon later shows up at his house for their scheduled date, where they apologize. Meanwhile, Oswald gets a promotion to Global Parcel's "angel of death," where he must inform customers about their lost or damage

Directors: Brian K. Roberts
star
6.72
68 votes

#24 - Up on the Roof

Season 4 - Episode 26 - Aired 5/19/1999

After her wedding plans don't work out, Oswald's mother moves back to Cleveland and decides to open a beauty salon. Kate gleefully quits her job as Mrs. Louder's assistant after Mrs. Harvey offers her work at the salon. Mrs. Harvey needs someone to repair the roof of the salon, and Drew suggests Sharon. Sharon is unsure because she doesn't have any experience with roofing, but Drew convinces her to take the job. Mrs. Harvey demands that Sharon re-do the job after the roof blows off in a storm, while Sharon insists that she isn't responsible. Lewis and Oswald get into a spat after Lewis sides with Sharon. Lewis ends up moving out and staying inside a storage locker. Mrs. Harvey sues Sharon for the completion of the job. She later goes to see Drew, who mistakenly believes she is seducing him. Mrs. Harvey instead shows Drew a report that proves that Sharon screwed up; she didn't realize that she needed special roofers' nails. Drew, Lewis and Kate try to repair the roof on their

star
6.71
102 votes

#25 - Brotherhood of Man

Season 4 - Episode 27 - Aired 5/26/1999

The leader of the Dutch ownership group announces that he is giving everyone a one-month paid vacation while the store is remodeled – except for Drew.

Directors: Gerry Cohen
Writer: Brian Scully