List of The Drew Carey Show characters

This is a list of characters who have appeared on The Drew Carey Show.

Drew's marriages
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.
 * 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 – 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."
 * 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 (Cynthia Watros) – 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 home and their friendship blossoms. They were both reluctant to confess their feelings for each other, but they became a couple after Drew and 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.

Recurring characters

 * 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-Louder board of directors, he managed to obtain the position by having sex with Mrs. Louder, a practice 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. Louder. He also ends up in jail for selling drugs, but is released and continues his job at the department store. After leaving Winfred-Louder, 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. Louder have to talk it out. 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 Bell's office. Little was known about him, but he behaved in a sexist and unprofessional manner, including liaisons with at least one female staffer. 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 Louder (Nan Martin) – Mrs. Louder is one of the executives' "cougars" and partial namesake of the Winfred-Louder 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, Mrs. Louder occasionally gives him minor promotions throughout the series, but his personality clashes with her ruthless and businesslike nature. She is somewhat sex-obsessed and conducts a long affair with the boorish, lazy, and obnoxious Larry Almada, played by Ian Gomez. (In another episode we learn Almada is superendowed sexually.) Mrs. Louder is last seen accompanying Mimi and Steve on their honeymoon (she advises them that she is a voyeur but they are forced to take her with them, anyway). She is removed from power shortly after when a member of the board improvises a speech slurring ethnic groups and gays. The insulted employees begin to riot, gaining the attention of the bosses in Amsterdam, who replace the entire board of directors except, for some reason, Mr. Wick.
 * Robert Soulard (Mark Curry) – One of Drew's bosses at Winfred-Louder, Mr. Soulard was appointed by the Dutch as Mrs. Louder'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.
 * Beulah Carey (Marion Ross) – Drew's and Steve's mother, married to George Carey (Stanley Anderson). George Carey dies towards the end of the series' run, although not due to the death of the actor.
 * Kim Harvey (Adrienne Barbeau) – Oswald's mother, who wears tight clothes and sweaters with plunging necklines. Her sexiness caused the young Drew in his childhood to commit some embarrassing faux pas.
 * King Augustus Antonio Carey (Dakota and Ryan Williams (seasons 6–8) and Matthew Josten (season 9) ) – 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 (played by Matthew Josten). 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-Louder 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-Louder 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: despite this, he once put his teenybopper daughter Milan (Jessica Cauffiel) in charge of Winfred-Lauder.
 * Christine Watson (Wanda Sykes) – Hired to replace Nigel Wick as manager in season 7, falls in love with Drew.
 * Jay Clemens (Robert Torti) – Kate's handsome 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.
 * Mrs. Wick (Richard Chamberlain) – Nigel Wick's "Mum" Maggie, played by Chamberlain in drag. The character is clearly promiscuous, young Nigel having grown up with a series of "uncles" in and out of his life.
 * Chuck (Kelly Perine) – Security Guard/Head of Security at Winfred-Louder. Chuck is a fellow employee at Winfred-Louder who seems to have a friendly relationship with Drew, as he, in his first appearance in the episode "No Two Things Are Exactly Alike" in Season 1, he tips Drew to the person who complained about a fellow employee who became offended at a sexually offensive cartoon which he put on a memo in the hopes of boosting company morale. In Chuck's final appearance in the Season 5 episode "Drew and the Racial Tension Play", Chuck is among the many minority employees who become offended at the socially insensitive comments of senior company board member Arthur Crawford (Hansford Rowe) who try to solicit Drew to get Crawford to apologize for his comments or resign.