<Li> 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 and connoisseur 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 .) </Li> <Li> Lewis Kiniski (Ryan Stiles)--Forms a double - act with Oswald . Lewis, who 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 . </Li> <Li> 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 . </Li> <Li> 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 . </Li>

Who played oswald on the drew carey show