This is a list of characters who have appeared on The Drew Carey Show.
Main characters Actor Character Role Years Seasons Episodes123456789 Drew CareyDrew Allison Carey Assistant Director of Personnel 1995–2004 colspan=9 233 Diedrich BaderOswald Lee Harvey Delivery Man/Trainee Nurse 1995–2004 colspan=9 233 Christa MillerKate O'Brien Cosmetic Saleswoman/Rock and Roll Hall of Fame 1995–2002 colspan=7 184 Ryan StilesLewis Kiniski Janitor at DrugCo. 1995–2004 colspan=9 224 Kathy KinneyMimi Bobeck P.A./Floor Manager 1995–2004 colspan=9 232 Craig FergusonNigel Algernon Wick Drew's boss 1996–2004 colspan=6 colspan=1 170 John Carroll LynchSteve Carey Cosmetics Salesman/Stay-At-Home Husband 1998–2004 colspan=2 colspan=3 colspan=2 colspan=1 73Cynthia WatrosKellie Newmark Waitress 2002–2004 colspan=7 colspan=2 52
Notes Christa Miller only appeared in the first and second episodes in Season 8. Kathy Kinney is credited as a guest star in the pilot episode, but she is credited as Starring from the second episode on. Craig Ferguson was credited as Starring in all episodes of Season 8, but only appeared in 4 episodes. John Carroll Lynch appeared in 8 episodes in Season 8, and was only credited as Starring for the episodes he appeared in.
Drew Carey (Drew Carey) – Drew Carey is the main protagonist of the series. A perpetual "nice guy", for most of the series, he works in the human resources department of Winfred-Louder, a multinational department store chain. 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 co-worker Mimi Bobeck; both play endless, occasionally complicated, seriously mean-spirited pranks on each other until she becomes his sister-in-law, after which they still dislike each other. 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 known makeup addict 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 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 claims to have slept with both Joe Walsh and Peter Frampton. Later on, Mimi becomes more of a friend to Drew (they agree to put their feud on hold while Mimi dates and later marries his brother, Steve) and a loving, if unconventional, mother to Gus. Early in the series, it was revealed that Mimi was Catholic and of Polish ancestry, and inherited the title of Duchess of Kraków after her aunt died. (Starting in 2009, Mimi/Kinney resurfaced as a guest on The Price Is Right, hosted by Drew Carey since October 15, 2007, during the show's April Fool's episode, first in 2009 as a model and then ransacking Mike Richards' position as executive producer on the show, in 2010. Carey usually promotes Kinney's next project during the closing of that episode.) Lewis Kiniski (Ryan Stiles) – Forming a double-act with Oswald, Lewis is tall, gangly, and perpetually bemused. 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, which conducts bizarre experiments. 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. 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." 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. 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. Aside from Carey, Bader is the only cast member to appear in every episode of the series. The name of Bader's character is a reference to Lee Harvey Oswald, the gunman who assassinated President John F. Kennedy. 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 and good with her fists. 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). She 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 (usually men surnamed Johnson), which he does in most episodes. He is almost always referred to as "Mr. Wick", and his first name, Nigel, is rarely used. In the show's first April Fool's Day episode, Wick was shot in the crotch with a crossbow by an employee (named Johnson) whom he had just fired. Wick had to have one of his testicles removed. Wick also lost a toe and a nipple in a fox hunt that went terribly wrong. Craig Ferguson initially auditioned at Warner Bros. for a role as a Hispanic photographer on Suddenly Susan, and after he failed his audition (with the role instead going to Cuban-American actor Nestor Carbonell), 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, Ferguson broke the fourth wall and began talking to the audience at home in his regular Scottish accent. Steve Carey (John Carroll Lynch) – Drew's straight but cross-dressing older brother (in reality John Carroll Lynch is 5 years younger than Drew Carey). He came to Cleveland and got a job in the cosmetics department at Winfred-Louder. 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.
Drew's marriages Much of the show's humor revolved around Drew's single life. 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. Mr. Wick (Craig Ferguson) - Drew's boss for the majority of the series, desperately wanted a spouse when his visa expired and he was threatened with deportation. He bribed Drew with a promotion and several benefits to get Drew to marry him in Vermont. They stayed married for just over a year to throw off any suspicion from the INS. Drew kicked Mr. Wick out of his house once Wick became too "clingy" with Drew's friends and life. 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 married 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 rarely seen again. Lewis helped her through something. He tried to have a relationship with her, but she refused. Kate O'Brien (Christa Miller) – 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 Impotent Bisexual Bigamist."