Drew Allison Carey Sr. (Drew Carey) - Drew Carey is the main protagonist of the series. He is a perpetual "nice guy." For most of the series, he works in the human resources department of Winfred-Lauder, a multinationaldepartment store chain. He's portrayed as a lovable loser, though he's the most successful of his group of friends. Drew is the founder and co-owner of Buzz Beer, a coffee-flavored caffeinated beer (at the time, such drinks were legal but uncommon in the United States). He has a long-standing feud with Mimi Bobeck; his pranks have included destroying her clothes, shredding her vacation requests, and masquerading as Antonio Banderas to taunt her.
Mimi Bobeck (Kathy Kinney) - Mimi Bobeck is Mr. Wick's assistant/secretary and the main antagonist of the series. Much like Fonzie from Happy Days and Steve Urkel from Family Matters, the Mimi character was originally a one-time character, only appearing in the pilot episode. She is an overweight woman who wears a lot of makeup, yet has a very high but unstable self-esteem. (As an in-joke, Mimi's mother was played by Tammy Faye Bakker.) Mimi is Drew's nemesis; she vowed to make Drew's life a living hell after Drew denied her a job based on her makeup. Mimi's pranks have included gluing Drew's hand to a pornographic magazine, covering Drew's desk with garbage, and eventually sending Drew to China while he is unconscious. She is also known for calling him "Pig" and "Doughboy." Mimi's past has a lot of connections to the world of music; she often talks about being a roadie for Foghat and was married to Eddie Money for two weeks after appearing at his first concert. Additionally, she admits to sleeping with both Joe Walsh and Peter Frampton. Frampton still carries a torch for Mimi; he has a tattoo of her likeness on his chest. Later on, Mimi becomes more of a friend to Drew (they agree to put their feud on hold while Mimi dates/marries Steve) and a good, if unconventional, mother to Gus. Early in the series, it was revealed that Mimi was of Polish ancestry, and inherited the title of Duchess of Kraków after her aunt died. However, the episode with this content received a great deal of complaint from the Polish community, and all mention of Mimi's heritage has been removed from the show (with alternative footage placed over these bits in syndication). Starting in 2009, Mimi resurfaced as a guest on The Price is Right during the show's April Fool's episode (hosted by Drew since October 15, 2007), first as a model (2009) and ransacking Mike Richards' position as executive producer on the show (2010). Carey usually promotes Kinney's next project during the closing of that episode.
Lewis Kiniski (Ryan Stiles) - Forms a double-act with Oswald. Lewis, who is tall, lanky, and blonde, is in his forties and can be counted on to nonchalantly say bizarre and offensive things. Ryan Stiles once described Lewis as "Not even a character at first, just a creep really." He possesses an IQ of 162, but works as a janitor for a company called DrugCo. Due to accidentally releasing a strain of bacteria into the population, he was busted down to janitor from a position that required him to wear a lab coat. It's uncertain if he was a scientist or lab assistant, though it's possible he was joking. At one point, he posed as Drew to take his physical exam for him, unexpectedly taking a psychiatric exam as well. He tried to give answers which he thought suited Drew's life and situation, and the results showed him to be mentally unstable and possibly criminally insane. He mentioned in one episode he was adopted.
Oswald Lee Harvey (Diedrich Bader) - Lewis's slightly shorter, dark-haired friend is the dumb one of the double-act, which tends to be his most distinguishing characteristic. Lewis described him once as a "man-child stuck in a sort of prolonged adolescence." At one point Oswald trained to be a nurse, but he proved unsuitable. Oswald was a deejay at the beginning of the first season but later on became a delivery driver for Global Parcel (a fictional package-delivery service whose uniforms are modeled after those of UPS). He later attempted to become a nurse, but he failed the required tests. Drew later got him a job as a delivery man for Never Ending Store, but Oswald was injured on store property. After receiving damages, he bought the Warsaw. His name is a play on Lee Harvey Oswald. In the episode Bus-ted, it is revealed that Oswald joined the group of friends to replace Adam, a childhood friend who fell through the ice on a lake.
Kate O'Brien (Christa Miller) - Friends with Drew, Lewis, and Oswald since they were kids. Kate is a bit of a tomboy and a hothead. She and Oswald almost got married at one point, but she called it off just after Oswald threw her a surprise wedding (essentially leaving Oswald at the altar). Kate later found out about Drew's long-standing crush on her at their high school reunion, and she realized that she had feelings for him too. They dated for a season (even becoming engaged) but broke up when they disagreed about having kids. Drew and Kate were married for a short time in a later season, although this was illegal, as Drew had just become married to his old girlfriend, Nicki. Eventually, Drew's sham was discovered and Kate felt betrayed. Drew eventually regained Kate's trust and they became friends again. Kate left at the beginning of the eighth season, marrying a Naval aviator and moving from Cleveland to Guam.
Nigel Algernon Wick (Craig Ferguson) - Drew's boss after the first season, replacing Mr. Bell (Kevin Pollak). English, crude, boisterous and offensive, he was also a cocaine addict before he was forced to go into rehab. For some time, he and Drew were in a same-sex marriage (technically a civil union) in order for Mr. Wick to get his green card and Drew to get his job back. When he first appeared on stage in guest episodes in the last two seasons he was greeted with thunderous applause. Wick always had unusual methods of firing employees (and nearly always fired someone named Johnson). He is almost always referred to as "Mr. Wick," and his first name is rarely used. In the show's first April Fool's Day episode, Mr. Wick was shot in the crotch with a crossbow and had to have one of his testicles removed (a gag that was referred to for the rest of the series). Wick also lost a toe and a nipple in a fox hunt that went terribly wrong. Craig Ferguson initially auditioned at Warner Brothers for a role as a Hispanic photographer on Suddenly Susan, and after he failed his audition, the casting director referred him to The Drew Carey Show which was auditioning across the studio. Ferguson, who is Scottish, played the role with an over-the-top posh English accent "to make up for generations of English actors doing crap Scottish accents." At the end of one episode, though, Ferguson broke the fourth wall and begin talking to the audience at home in his regular Scottish accent.
Steve Carey (John Carroll Lynch) - Drew's cross-dressing brother. He came to Cleveland and got a job in the cosmetics department at Winfred-Lauder. He fell in love with Mimi and after one season of dating they married in a ceremony in Drew's backyard, with Drew officiating along with an online minister from an Internet website. In later seasons the concept of Steve being a cross-dresser is abandoned entirely with little explanation (though it is hinted that he gave it up to make Mimi happy). He left, along with Kate and Wick, early in the eighth season.
Kellie Newmark (Cynthia Watros) - Drew's childhood friend. She has had a crush on Drew since high school but never told him. She was married but her husband cheated on her with her sister. Her mother is an alcoholic and leaves her father, eventually hooking up with Lewis. After Kate leaves, Drew realizes that he loves Kellie. Drew is afraid to tell Kellie because it may ruin their friendship like it did with Kate. After Lily leaves Drew, they confess their feelings for each other. When Kellie comes out while Drew is talking to his dad and asks Drew what they are going to do about their feelings for each other, Drew's dad falls off the roof and dies. Eventually during the beginning stage of their relationship Kellie finds out she is pregnant with Drew Jr. but won't marry Drew because she doesn't think he is ready for marriage. During the finale she decides Drew is ready. But her water breaks and she and Drew get married right when the baby is born.
Much of the show's humor revolved around Drew's single life (in real life, Drew was engaged for the first time in 2007, shortly after becoming a game show host). However, Drew was married a number of times during the show's run. His spouses during the series were:
Diane (Nicole Sullivan) - A cocktail waitress Drew met on a business trip to Las Vegas. She tricked Drew into marrying her because she believed having a husband would give her an edge in winning custody of her children. Drew agreed to help her with the social workers, and they divorced a week later.
Nicki Fifer (Kate Walsh) - A real estate agent whom Drew dated and became engaged to; she dumped him after gaining a large amount of weight while they were dating (and, in her own words, "couldn't be with a man who loved to eat"). She lost the weight, got married and came back to Drew after her divorce (when Drew had just left a mental institution). Drew asked her to marry him on an impulse, and she agreed. Unfortunately, Drew also got married to Kate soon after (thus becoming a bigamist) and she left him. Nicki returned later, having regained all her previous weight, and attempted to kill Drew because she blamed him for all the recent problems in her life. Drew let Nicki stay at his house until she could get back on her feet, after which she was never seen or heard from again.
Kate - The love of Drew's life and his best friend since childhood, Drew and Kate first broke off their engagement after a disagreement about having kids. After Drew's stint in the mental hospital, Kate realized that she still loved Drew and asked him to marry her. Drew agreed (despite having recently married Nicki and still being married to Mr. Wick) and kept both his marriages a secret for a time. Both wives discovered the situation, and Kate, furious, dumped Drew and told the newspapers about the situation; Drew became known as "The ImpotentBisexualBigamist."
Lily (Tammy Lauren) - A Southern belle who met Drew after Oswald and Lewis started a campaign to find him a wife. Drew brought Lily to Cleveland and attempted to establish a relationship with her, but found it difficult to deal with Lily's night terrors. Drew ended up proposing to Lily on three different occasions: once in his house, another in a movie theater, and finally, back at his home again. After Drew tore up all of his pre-determined wedding plan receipts, Lily agreed to marry him. Lily left Drew after the wedding, driving off without him after giving Drew his ring back. At the reception, Drew and Kellie expressed their hidden love for each other and began their relationship, which would also lead to Drew's final marriage.
Kellie Newmark - Drew's childhood friend who was introduced in the eighth season. Drew went to a strip club and discovered that Kellie was working as a stripper to support herself after her divorce from her husband. Drew takes her into his house and their friendship blossoms. They were both reluctant to confess their feelings for another, but they became a couple after Drew & Lily's wedding. Kellie soon becomes pregnant, but refuses to marry Drew for another eight months. On their wedding day and the series finale, Kellie gave birth to Drew Jr.
Larry Almada (Ian Gomez) – One of Drew's co-workers, Larry is a bumbling and somewhat unprofessional employee who is often willing to resort to less than savory methods to gain the upper hand. During a competition to determine the new employee representative on the Winfred-Lauder board of directors, he managed to obtain the position by having sex with Mrs. Lauder, a practice that he repeats several times after being dumped by his wife. He loses his job on the board shortly after receiving the promotion, but continues his secret relationship with Mrs. Lauder. He also ends up in jail for selling drugs, but is released and continues his job at the department store. After leaving Winfred-Lauder, he set up a reasonably successful dating service which later expanded into a television chat show.
Gerald Hawthorne Bell (Kevin Pollak) – Drew's boss for the show's first season. Mr. Bell only appeared in person for his last appearance. He gets caught having relations with a woman in his office and he and Mrs. Lauder have to talk it out, but when he appears, he is wearing a Santa costume. We only heard his voice on Drew's speakerphone, despite the fact that Drew had his desk very close to Mr. Bell's office. Little was known about him, but he did not come across as a nice person. He seemed sexist and self-centered and had an office romance with a staff member (unlike Drew's romance with Lisa, Bell was only after the sex). In the last episode of the first season, Mr. Bell finally appeared on camera as he was seen leaving his office after getting fired from the store. The running joke of his never being officially seen until this moment is referenced in dialogue when he says; "What's the matter, Carey? You act like you've never seen me before!"
Fran Lauder (Nan Martin) – Mrs. Lauder is one of the executives' "cougars" and partial namesake of the Winfred-Lauder corporation who originally inherited the store from her dead husband. She is the CEO of the company that owns the department store, and retains her position even after the corporation is bought out by a larger company located in Amsterdam. As the head of the store, she thinks very little of Drew, and openly expresses surprise at the assertion that he still has dreams of becoming more successful, although on occasion she doesn't hesitate to refer to Drew as a good employee. Mrs. Lauder occasionally gives him minor promotions throughout the series, but his personality clashes with her ruthless and businesslike nature. She is last seen accompanying Mimi and Steve on their honeymoon, but is removed from power shortly after when a member of the board improvises a speech slurring every major ethnic group. The insulted employees begin to riot, gaining the attention of the bosses in Amsterdam, who fire and replace her along with the entire board of directors except for Mr. Wick.
Robert Soulard (Mark Curry) – One of Drew's bosses at Winfred-Lauder, Mr. Soulard was appointed by the Dutch as Mrs. Lauder's replacement after the latter was fired along with the original board of directors. Slightly more open-minded than his predecessor, Mr. Soulard agrees to listen to the employees after he is made the new boss, and quickly appoints Drew to be the new Store Manager when Mr. Wick's incompetence gets him sent to Toledo for retraining.
King Augustus Antonio Carey – Gus is Steve and Mimi's son as well as Drew's nephew, who saved Mimi from being fired by Drew in the episode "Drew Pops Something On Kate". Just as Drew is about to fire Mimi, he kicks while in the womb for the first time, causing him to feel compassion for Mimi and preventing him from firing her. Gus was born while Drew was in a coma, and his spirit (voiced by Jon Polito) met Drew up in Heaven before being born. After hearing Drew make jokes about how horrible Mimi was, Gus was afraid to be born. Drew convinced him that Mimi would be a good mother by going back down to Earth and spending time in the baby's body. Drew told this story to the others after coming out of his coma, but nobody believed him. Gus was an infant for most of his time on the show, but received an age boost (putting him somewhere between 5 and 6 years old) for the final season. He burns down his house, initially thought to be with a wood-burning kit that Drew gives him as a gift. Since Mimi and Gus had nowhere to live, Drew offers his home to them, and they stay there almost until the end of the show. It was later discovered that Gus was a pyromaniac and intentionally started a fire in the house.
Lisa Robbins (Katy Selverstone) – Drew's girlfriend from season one, she is prevented from dating him as the rules at Winfred-Lauder do not allow management to participate in romantic relationships with their employees. Although this initially forces them to hide their relationship in public, they eventually find a way to overcome this obstacle. She vies for a job as the head of the personal shopper department to become a member of the store's management, prompting a competition with fellow applicants Kate and Mimi. Lisa begins dating Drew after she gets the job, but after a failed attempt to live together they agree to break up. She leaves her dog, Speedy, behind to stay with him and departs for good after her marriage in the second season.
Lord Mercer (Jim Piddock) – An extremely wealthy Englishman, who bought Winfred-Lauder and became the new owner after the Dutch divested themselves of the company/store(s). He also brings back Mr. Wick, saying only Englishmen know how to run a business.
Christine Watson (Wanda Sykes) – Hired to replace Nigel Wick as manager, falls in love with Drew.
Jay Clemens (Robert Torti) – Kate's boyfriend from season one.
Evan (Kyle Howard) – Co-owner of Never Ending Store with his brother, Scott (of the two bosses, he is regarded as the 'nice' one). He is a Zen-seeking Buddhist who promotes peace and support, although he himself has a life coach, sees a family therapist with his brother, and takes anti-anxiety pills. He has a tenuous relationship with Scott because they spend so much time together.
Scott (Jonathan Mangum) – Co-owner of Never Ending Store with his brother, Evan. He is more business-minded than Evan, and can get very irritated by Evan's peace-seeking way of life. He teaches computer classes during the summer.