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  • Awesome Music: The Presidents of the United States of America's cover of Ian Hunter's "Cleveland Rocks" used for the show's theme song. (Well, one of three.)
  • Base-Breaking Character: Mimi is either hilarious, witty and entertaining, or very off-putting. The fact that a lot of her attacks on Drew cross the line is rarely dealt with.
  • Big-Lipped Alligator Moment: The show is pretty chock full of them, but one that stands out is when the crew decides to go to a midnight showing of The Rocky Horror Picture Show for almost no reason and then gets into a dance off with fans of The Adventures of Priscilla, Queen of the Desert. The dance fight is broken up by police and the characters are shown back at Drew's house where the only mention of the events is Oswald soaking his feet and complaining about wearing high heels.
    • This is especially common for the occasional "What's Wrong With This Episode" episodes. Every now and then for April Fools' the show had a contest to give a prize to whoever could point out the most errors. These episodes are guaranteed to be more Big-Lipped Alligator Moment than actual episode as the characters turn into puppets, the show is shot entirely in The Sims, actors switch places, or a hundred other random occurrences. Reruns point out the mistakes with on-screen GFX.
    • There is also the "Drew Live" episodes which are essentially cross overs with Whose Line Is It Anyway? in which the entire episode is shot live and the actors will at any random point be forced to ad lib a new line, or break from the show entirely to play out a Whose Line is it Anyway? improv game.
    • Daffy Duck appeared in the season 3 finale looking for a job at Winfred-Louder, in the opening scene. After Daffy leaves, the incident is never brought up again. You'd think that if a classic cartoon came into the office, most people would be talking about it for hours on end!
      • A lot of the cold openings qualified. Another example is one where Drew's office is attacked by aliens. Turns out it's All Just a Dream that an alien Drew had.
    • The musical numbers generally come across as this, at least for people used to them. They follow the 1950s musical rules and not the 1990s sitcom rules.
    • Season 4's "Drug Co." is essentially a Bizarro Episode where Drew and the gang break into Lewis' workplace to rescue his dog Speedy. They find a lot of strange things such as a human-like insect, holographic dobermans, a crystal ball that makes you smarter when you hold it, etc. The funny thing is, Drew and his friends don't seem very perplexed by any of these strange goings on (probably because they already know Drug Co. is a place where strange experiments are done), and after these events, they're never brought up again.
    • In response to an elaborate prank involving booby-trapping her desk Rube Goldberg style, Mimi drugs Drew and ships him to China. He wakes up on the Great Wall.
    • In one episode, Kate literally dates the Devil. She only escapes eternal damnation after he learns she's no longer a virgin.
      Drew: If you want a virgin, take Lewis!
      Lewis: I can cook!
  • Crosses the Line Twice:
    • Mr. Wick's Running Gag of firing people, typically Johnson. Here's an example:
    Mr. Wick: Carey, pick a name out of the hat. (Drew pulls out a scrap of paper) Jones? You're fired.
    • In "Drew and The Gang Law", Drew decides to join a class action law suit to fight the law that prevents him and his friends from associating. It crosses the line when it's clear that every member of the suit except for Drew is or appears to be a career criminal. Then as Drew leaves, another member shows up dressed in a Klan robe. For bonus points, the lawyer representing this group is black.
    • "Drew Can't Carry A Tune" opens with the gang attending church. Drew watching a football game on a portable t.v., while the the priest is informing the mass of another priest's death. Drew bursts into excited cheers over a team he bet money on winning and then points out that Kate is Catholic to draw attention away from himself.
    • In "When Wives Collide", Kate and Nicki get back at Drew for marrying both them without informing the other by throwing a dummy dressed as Nicki out the window. The dummy strikes Drew's car and in his panic, he runs over it four times before realizing it isn't Nicki.
    • Everything about the b-plot in "Daddy Dearest" where Lewis accidentally eats a human liver that Oswald was tasked with taking care of. Perhaps the best moment is his awkward meeting with the man's widow who also informs him the liver had parasites in it.
  • Ensemble Dark Horse: Craig Ferguson's Mr. Wick was fairly popular for being so over-the-top.
  • Fan-Preferred Couple: Drew/Mimi was very popular back in the day, especially considering Drew will always come to her rescue when she needs him.
  • Foe Yay Shipping: Drew and Mimi's rivalry was so intense, and they wasted so much time fighting each other, that it really looked like this trope. It helps that they were friendlier to each other in the first season, which contained some extremely bare bones friendship moments.
  • Harsher in Hindsight:
    • The season two episode "Cap-Beer-Cino" has two humorous moments where Wick thinks Drew is suffering from alcohol and drug addiction. Fast forward to season four's "Golden Boy" where Drew discovers Wick has a drug problem and makes the latter go to rehab.
    • In "Hush Little Baby" when Steve is leaving the house, Mimi throws him a suitcase, saying that she has it in case Steve ever cheated on her. Two seasons later Steve does end up cheating on Mimi.
    • Season 2's "The Devil You Say" sees the Devil trying to claim Kate's soul. Drew tries to break that deal with a game of pool, but his first wager is that he'll have to stay in his middle management job and never get promoted if he loses. The Devil suggests that was gonna happen anyway, causing Drew to lose his cool. Funny so early in the show's run, but over the seasons, Drew is often denied promotions and always ends up back in his cubicle in those rare times he does get promoted. Even after Winfred-Louder goes bankrupt and is replaced by an online retailer, Season 9's "The Passion of the Wick" ultimately ends with things back to the way they were, especially with Drew back in his cubicle.
    • One of the reasons fans ignore the last few seasons is because Kate dumping Drew and marrying someone else, makes the majority of the series one long "Shaggy Dog" Story.
    • A recurring element of the show is that Drew is overweight and okay with it, he has a good life and enjoys eating. The real Drew Carey revealed that he struggled for a long time hating how he looked, especially on camera, but after he took over The Price Is Right his brother died of a heart attack and that shook him into better eating habits and exercise.
    • In Season 4, Drew refuses to sell his house so Winfred-Louder can redevelop the neighbourhood as a new mall with them as an anchor tenant, blocking the plan and leaving the company with dozens of empty houses. Fast forward three years and the store is sold to a series of new owners, collapsing entirely by the beginning of Season 8. Granted, with the management style always shown by the store's higher-ups regardless of ownership, that may have been inevitable.
    • Lewis and Oswald screw up Buzz Beer's booth at a convention in "Buzzie Wuzzie Liked His Beer" so badly that Drew punishes them as if they were children and forbids them from certain activities, including not letting The Cat in the Hat in the house. Oswald naturally doesn't get the reference, prompting Lewis to explain, "It's a book. They haven't made the movie yet." Three years later, a movie version did come out, and it didn't go over very well (especially with the estate of the book's author).
  • Hilarious in Hindsight:
    • Even though the sight of Lewis and Oswald dressed as Batman and Robin is already funny, it only got funnier when Diedrich Bader (Oswald) went on to voice Batman.
      • A season 7 episode guest starred none other than Adam West and he spoke directly to Diedrich Bader (Oswald) several times. This series features Batman talking to Batman.
      • For extra points, Oswald's name is basically a reference to two iconic Batman villains — Oswald Cobblepot (the Penguin) and Harvey Dent (Two-Face).
    • The jokes about Drew's weight gain have become this since Drew Carey's real-life drastic weight loss
    • In Season 6's "Mimi's a Partner", Drew complains about having nothing to do while being unemployed.
      "I'm sick of just sitting around watching game shows, so somebody COME ON DOWN, and kill me!"
    • In "Eat Drink Drew Woman", Christine's father expresses gratitude that she did not become a lesbian after her divorce. Her actress Wanda Sykes came out as gay seven years after that episode first aired.
  • Ho Yay:
    • Oswald and Lewis. Lewis had to enter marriage counseling with Oswald and his fiancee because he plays a bigger part in Oswald's life than Oswald's girlfriend.
    • In one episode where Lewis thinks he's dying from a cold, he decides to go to the Warsaw naked. Mr. Wick asks for Lewis' help moving his car, compliments Lewis on his skill with a razor, and then the two of them enter the Warsaw naked together.
      Mr. Wick: Oh, thank you, Lewis! I've never felt so free!
  • Nightmare Fuel: The puppet segment from What's Wrong With Episode II.
  • Retroactive Recognition:
    • A lot of actors who became famous on Scrubs had small bit roles on The Drew Carey Show beforehand. Sam Lloyd (Ted the Lawyer) appears as a delivery man in Season 3's "The Batmobile", Aloma Wright (Laverne Roberts) plays a security officer in "Good Vibrations", Nicole Sullivan (Jill Tracy) tricks Drew into marrying her in "Drew Gets Married", and Neil Flynn (The Janitor) was one of Kate's boyfriends in one episode. Not to mention Christa Miller (Jordan) starring in this show as Kate.
    • A pre-NCIS Pauley Perrette as Drew's girlfriend Darcy for the three episodes where he was in a band.
  • Seasonal Rot: The last two seasons which certainly felt like the showrunners were running out of ideas, often about Drew trying to get a girlfriend. This was not helped at all by the leaving of Kate's actress.
  • Strawman Has a Point: Mimi, in the pilot episode. Okay, she was way out of line calling Drew out during her job interview, accusing him of being sexist (which he wasn't), and making a scene in front of the other workers, but in Mimi's defense, Drew did not handle her interview very well. He has the gall to tactfully say to her "We WILL be interviewing a lot of people for this job", which is, as Mimi puts it, a tactful way of saying, "We're not hiring you." Any HR director will tell that you do not say anything like that to an applicant as it's very discouraging to them, and it makes the company look bad. Mimi is understandably pissed by this and deduces that if she were hot-looking he'd have hired her right away. Drew insists this isn't the case, except in the very next episode, we see him hiring a woman (Lisa) who is very attractive, and actively flirts with him, and eventually starts dating him! When watching the first two episodes, and seeing all this unfold, it's not hard to side with Mimi and think maybe she had a point.
    • Mr. Wick in his debut episode. Throughout the series Drew complains about not moving up the company ladder, and being stuck in a dead-end job as Director of Personnel. Wick point-blank tells Drew that he simply is not capable of handling a higher management position. If one watches several other episodes where Drew has to fire somebody, even for legitimate reasons (stealing, assaulting a customer, etc.), Drew will often try to find ways to keep said employee working at Winfred-Louder, or he'll be too intimidated to fire the person, usually out of guilt. Given that a manager's position requires someone with a bit more backbone, and the ability to tell when someone doesn't belong in a company, it's clear that Drew really doesn't deserve to be a manager (not that Wick does either as he's shown to be a whiny Jerkass).
  • They Wasted a Perfectly Good Character: Kate's mom, played by Christa Miller's aunt Susan Saint James. She only appears once, in a single episode of the first season.
  • Unintentional Period Piece:
    • The "Cleveland Rocks" intro features the cast at a Cleveland Indians tailgating party, wearing uniforms with the team's then-mascot and logo Chief Wahoo on it. Chief Wahoo was retired after the 2018 MLB seasonnote  due to it being considered racially insensitive to Native Americans, and the team itself was renamed the Guardians between the 2021 and 2022 seasons.
      • The full version of the intro, seen on "Strange Bedfellows", features a Jacobs Field sign on the entrance of the Indians' stadium. Jacobs Field was renamed Progressive Field in 2007.
    • Not to mention Kate referencing the Cleveland Browns' then-currentnote  hiatus and its players and staff's then-recent relocation to Baltimore in The Teaser of "Hello/Goodbye" as Drew, Oswald and Lewis a tape recording of a Browns game they attended in 1989 to place bets and to see how it ended because they missed it the first time (and even then they still don't know how it ended because the tape ended early).
  • Unintentionally Unsympathetic: Steve is given the Sympathetic P.O.V. when his jealousy over Drew's professional success causes him to rant multiple times. However not only did Steve later admits that he has always resented Drew because he liked having their parents to himself, but he was a Big Brother Bully who took his resentment up to eleven to the point of being a Barbaric Bully.
    • This revelation also becomes Harsher in Hindsight as Drew has gotten him a job and allowed him to live with him multiple times, allowed him and Mimi to date and have their wedding at his house, even officiating it. So this revelation just makes Steve come across as an Ungrateful Bastard given the All Take and No Give nature of his and Drew’s relationship. There’s also the fact that Steve never actually got over it he just took a job as a prison guard so he could take his hostility out on the prisoners instead of Drew.
      • Finally he ultimately abandoned Mimi and his son.
  • The Woobie: Drew certainly goes through a lot more crap than he deserves to. Mimi also has shades of this, but her Woobie moments are scarce.

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