The first season's opening credits consisted of a caricature of Carey's face wearing a yellow tie—singing the Robert McGuire-penned "Moon Over Parma". The song was trimmed for the opening sequence, and the reference to Eastlake in the line "Guide her to Eastlake underneath your silvery light" was changed to a reference to Cleveland to stay in theme with the show.

In the first season, Drew and Mimi worked under Mr. Bell, who existed only as a voice on Drew's speakerphone, excluding the season finale (his final episode, played by Kevin Pollak) wherein he is fired by Winfred-Louder's new owners. Other characters that appeared exclusively in this period were Drew's hillbilly neighbor Jules and his family. Drew's first girlfriend Lisa was introduced in this season, as was Jay, Kate's love interest who used to attend the same high school as Drew and his friends. Both characters lasted until Season 2, where they were quickly written out of the show in the early episodes.

Nine of the episode titles were related to chemistry in some way, with names such as "The Joining of Two Unlike Elements Is a Mixture" and "Isomers Have Distinct Characteristics". However, this theme was abandoned by the end of the season.
"Moon Over Parma" was phased out during the second season by "Five O'Clock World" sung by The Vogues. This season introduced openings that paid homage to music videos which included the cast dancing and singing around the various sets of the show.

In the third season, the opening theme was changed to "Cleveland Rocks", a cover of an Ian Hunter song performed by The Presidents of the United States of America. The video consisted of shots of Cleveland ending with their ballpark. This change lasted until the second "wave" of the show ended, with the finale of Season 7.

The man who took over Mr. Bell's job after his firing was Nigel Wick, who served as a foil for both Drew and Mimi in the workplace. During this period, Drew and Mr. Wick also periodically took the top management job away from each other. This would usually result in Drew ending up back at his old job as assistant director of Personnel and Mr. Wick would miraculously retain his job as manager. By the end of Season 7, they were both Co-Managers before Winfred-Louder was closed down (albeit after undergoing drastic changes to stay in business). A recurring subplot involved Drew and his friends running a side business called "Buzz Beer," a microbrewery conceived through the concept of mixing coffee and beer. While several brand concepts and promotional stunts were plotted by Drew and his friends, their product failed to gain any true notoriety.

Kate and Oswald became closer and eventually became romantically involved and almost married during the third season, but Kate stood Oswald up at the altar. Kate and Drew also became romantically involved and were on the verge of getting married, but they called it off when they realized they did not feel the same about the prospect of children. Drew's cross-dressing brother Steve was introduced during this period. He eventually fell in love with Mimi and they had a child together, Gus (whose name was decided by means of a contest).

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199 ^ Christa Miller only appeared in the first and second episodes in Season 8.
299 ^ Kathy Kinney is credited as a guest star in the pilot episode, but she is credited as Starring from the second episode on.
399 ^ Craig Ferguson was credited as Starring in all episodes of Season 8, but only appeared in 4 episodes.
499 ^ John Carroll Lynch appeared in 8 episodes in Season 8, and was only credited as Starring for the episodes in which he appeared.
• Beulah Carey (Marion Ross) – Drew's mother
• George Carey (Stanley Anderson) – Drew's father
• Kim Harvey (Adrienne Barbeau) – Oswald's mother
• Mother Bobeck (Tammy Faye Bakker) – Mimi's mother
• Gigi Bobeck (Lynn Wanlass) – Mimi's sister
• King Augustus Antonio Carey (Dakota and Ryan Williams, Matthew Josten) – Drew's nephew, Steve and Mimi's son
• Misty Kiniski (June Lockhart) – Lewis's mother
• Nikki Cox as Drew's cousin Kirsten Carey, who briefly dates Mr. Wick in "Drew's Cousin" (Season 3, Episode 25)
• Shirley Jones as Drew's lady friend Celia (Season 4, 3 Episodes)
• Caroline Rhea as Drew's date Bonnie (Season 2, 2 Episodes)
• Pauley Perrette as Drew's girlfriend Darcy (Season 4, 4 Episodes)
• Dan Castellaneta as Sal, the King of Poland in "Two Drews and the Queen of Poland Walk into A Bar" (all of his scenes were cut from reruns after complaints from the Polish community) (Season 2, Episode 20)
• Hal Linden as Mr. Van Zandt in the episode "Brotherhood of Man" (Season 4, Episode 27)
• Mark Curry as Robert Soulard (Season 5, 6 Episodes)
• John Ratzenberger as himself in Drew Live III
• Eddie Money as himself, the former husband of Mimi Bobeck in "Drew's Stomachache" (Season 5, Episode 10)
• Penn & Teller as Fenn and Geller in "Drew Meets Lawyers" (Season 1, Episode 6) and "See Drew Run" (Season 2, Episode 17)
• David Cross as Earl in "Drew and the Unstable Element" (Season 1, Episode 13) and "Two Drews & the Queen of Poland Walk into a Bar" (Season 2, Episode 20)
• Tim Allen as himself in "The Front" (Season 1, Episode 17)
• Norm MacDonald as Simon Tate in "The Bully You Know" (Season 2, Episode 4)

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The show initially finished outside of the Top 30 in the Nielsen ratings, at #48. In the second season, ratings improved, and the series jumped into the Top 25, remaining there for the next three seasons as well. The sixth season finished just outside of the Top 30, at #37. This is attributable to the erosion of network audiences that began in the late 1990s.

After its sixth season, ABC and Warner Bros. Television negotiated to keep the series on through the 2003-04 television season, which would place it in its ninth season. However, in its seventh season, The Drew Carey Show experienced a dramatic ratings drop, as did several other ABC series. A schedule move by ABC for the eighth season resulted in even worse ratings, falling out of the Top 100. At midseason, ABC placed the series on hiatus, and attempted to get out of the contract with Warner Bros. Television. When they were unable to, ABC finished the eighth season in the summer, and decided to burn off the ninth and final season during the summer of 2004. The series finale was viewed by a little over 5 million viewers.