The Ten Best THE DREW CAREY SHOW Episodes of Season Three

Welcome to a new Sitcom Tuesday! This week, we’re continuing our coverage on the best of The Drew Carey Show (1995-2004, ABC). Unfortunately, only the first season has been released on DVD. But as of this publication, you can find reruns on Laff!

The Drew Carey Show stars DREW CAREY as Drew Carey, DIEDRICH BADER as Oswald Harvey, CHRISTA MILLER as Kate O’Brien, RYAN STILES as Lewis Kiniski, KATHY KINNEY as Mimi Bobeck, and CRAIG FERGUSON as Nigel Wick.

As discussed last week, Season Three has many of the same qualities that make Two the series’ best — principally, it features a fine narrative balance between Drew’s home life and his work life, along with an appealing comedic energy that I’ve described as an “anything can happen” sensibility. What Three doesn’t have, however, is the sophomore year’s novelty — the lingering freshness that shakes hands with the audience’s newfound understanding of character and creates a moment of ideal reconciliation between the expected and the unexpected. By now, the show has over-relied on certain gimmicks — like musical numbers and casting stunts — and must reach even further to find shockable off-the-wall gags, like the first annual “What’s Wrong With This Episode” (which is typically reserved, as is the case this season, for entries that are designed normally but otherwise don’t have the natural Drew Carey oomph, and are therefore goosed with this unnecessary and non-character related additive). However, we’re far from the dire straits that the series will reach in the years ahead, so I must remind that Season Three is still Golden Era-adjacent. It’s just that when the show does resort to said gimmicks, it’s clear that they’re not only bigger than before, but also less narratively beneficial to the characters… And this is interesting because the third season of Drew Carey may be one of the series’ most character-dependent of the entire run — not with regard to either its gimmickry or its comedy (which is broader and less character-rooted), but with its storytelling, which is composed of several long-range arcs predicated on the emotional decision-making of the regulars: opportunities the show structurally allowed itself from day one thanks to its “Singles In The (Midwestern) City” slant. But this notion of character, and the show’s ability to motivate story and comedy through its leads, is something that warrants more discussion …

The Drew Carey Show has been able to survive so far with thin cartoon-like characterizations because the structural premise has proven so freeing and prosperous — it’s given the characters so much that they didn’t initially need to be as generous. But, in order to engage narratively with the romantic personal-life interests suggested above by the concept, it’s nevertheless true that — as always — the “buyability” of any development is contingent on whether or not we believe what choices the players make to get there. So, in having this year be less narratively episodic and by using several major and long-running arcs — most of them rooted in the personal lives of these characters (thus suggesting a tipping of the figurative scales that we’ll continue to see over the next few weeks) — the show is putting more faith than ever into their potential story-anchoring depths. (Seasons One and Two have arcs but, trust me, they are nothing like this year’s!) Generally, I don’t think the show ever impresses consistently when it looks upon its regulars to justify the romantic-drama (rom-dram) narratives it seeks to employ — all the while juxtaposing them against innately broad comedic gimmickry, which sometimes makes for a thrilling contrast, but can also beget a disconcerting disappointment if either element isn’t as well-realized as needed. But for Season Three, which I think is the first to really embrace the rom-dram notions more typical of Friends (personal) than NewsRadio (professional), I give more leeway — both because the show is at a healthier state overall (which means it doesn’t fail as much as upcoming seasons do) and also because I think the only way for the show to strengthen its characterizations is to put them in arcs that force the scripts to contend with their emotional underpinnings; in this regard, some of what we see here in these heady plots feel necessary.

I’m thinking specifically of Drew’s romance with Nicki (Kate Walsh), a realtor who doesn’t have much definition by way of comedy (that is, she has no pinpointable perspective that motivates laughs independently of plot and can therefore do little but set-up Drew’s jokes) but is defined by what she can provide via story: her former heftiness, which looms over her relationship with Drew until she, over the course of an 18-episode arc, has gained back so much weight that she cruelly leaves him — breaking their hasty engagement (motivated by the Kate/Oswald engagement, discussed below). As usual, I have mixed feelings. I wish Nicki was written better, but I love the backstory and what it means in relation to Drew. Additionally, I think her very burlesque “weight gain,” which begins in the second half of her arc and is so obvious and broad that it mitigates the sting of the ending (simply because what happens now seems inevitable), also undermines the sincerity of Drew’s feelings for her and how her problems hit to some of his own insecurities. Yet, ultimately, although the show doesn’t handle this perfectly, it still succeeds in deepening Drew’s character, and in providing him with an emotional vestment that’s more personal (see: the weight issues) than the more casual and even less defined relationship he had in Season One with Lisa. I don’t like every episode from this storyline, but I like many of them — and even when the plot drives the characters (as opposed to the preferred inverse) and the outcome seems a forgone conclusion, I don’t feel like I often feel at these junctures: that the characters don’t matter. Here, they do — and that’s exactly why some things work, and some don’t… Meanwhile, it also helps that their relationship accelerates alongside another arc that, arguably, has more personal ramifications for Drew: the surprise romance, and later engagement, of Kate and Oswald, two members of the show’s “core four.”

Okay. Again, mixed feelings. Kate/Oswald is the first romantic pairing within the regular cast. If it were the only romantic pairing within the regular cast, I might have a different opinion, because, as we saw with Friends, the more couplings, the less we believe and invest. With Kate/Oswald, their pairing is already a leap, not just because of how they were written earlier — the only indication of their suitability occurred last year when we learned they had lost their virginities to each other — but primarily because we know how Drew feels about Kate, for it was established in early Season One and it looked like, if there was ever going to be a regular couple, it would be them. Thus, by putting Kate with a regular who’s not Drew, the series has the responsibility to explore, with greater emotional stakes than with Jay or some other cardboard cutout, the notion of Drew/Kate, either as the means of finally pairing them, or as the means of finally allowing Drew to move on. This prospect gives the arc a raison d’être and helps overcome the inherent “huh?” we feel with Kate/Oswald. Yet, the year doesn’t fully commit to this necessary justification, for although Drew maintains his feelings for her and only half-heartedly gives his blessing, the show uses Kate/Oswald to neither progress or end Drew/Kate. Instead, the show pushes aside the actual character interests that this storyline suggests in favor of rom-dram story — culminating in Kate’s at-the-altar break-up with Oswald, which is as unmotivated as their pairing and is precisely the wrong development at this point; for without a substantive character-rooted cause, like her realized feelings for Drew, the story ends, like it apparently began, for no darn reason. Hindsight will tell us more — Season Four returns to the status quo and almost pretends like Kate/Oswald never happened — but it’s already clear the series denied its characters the emotional depth the storyline sought to offer. Next year has no Drew/Kate and no Kate/Oswald… so what did the characters really get from this? Nothing. What did we get? A couple of strong episodes… when the characters > story.

But not everything is even that rewarding. More flatly unappealing is a story that takes place in the office, but concerns personal feelings — Mimi’s decision to sue Wick after she learns that he planned to betray her in their failed harassment scheme. I’ll have more thoughts below, but here I’ll say that those two are so broad that an idea like such — heightened and clearly morally wrong — doesn’t seem ill-fitting based on what we know of them. Rather, what works against the arc is both, again, its slow, drawn-out plotting, and the fact that it’s “schmuck bait,” for we know the status quo won’t be disrupted and all we’re waiting for, basically, is the characters and their relationships to go back to normal. In contrast to other arcs, this seems more like story for story’s sake, without a lot of great character stuff resulting… Similarly, two early stories that run concurrently with the introduction of Nicki and the start of the Kate/Oswald relationship are personal narratives from characters in the professional realm. They are the firing of Larry (Ian Gomez), which leads to his staying with Drew and getting the entire gang arrested, and Mimi’s bizarre hoarding of a seemingly insane Wick, which begins after he’s traumatized during a storm. Appearing more amused by their plot interests than anything else, these stories’ laudable (and surprising) mingling with the other arcs still doesn’t offer the character riches we hope to find. With hindsight, this makes me wonder if Three’s experimentation with extended stories — and their varying degrees of success — is not partially responsible for the upcoming move away from the office (thereby disrupting the balance and limiting the show narratively, when it still needed freedom, especially with these characters)… However, Three is probably the show’s second best year, and with viewers still engaged, Drew Carey was riding high. So, as usual, I have picked ten episodes — out of an extraordinary 28 — that I think exemplify this season’s strongest. (They are listed in AIRING ORDER.)

Notable writers this year include: Bruce Helford (Roseanne, George Lopez, Anger Management), Clay Graham (Benson, Who’s The Boss?), Bruce Rasmussen (WingsRoseanne, The Middle)Joey Gutierrez (Martin, Raising Hope, Last Man Standing) & Diane Burroughs (Martin, Yes Dear, Still Standing), Lona Williams, and Bob Nickman (Roseanne, Mad About You, Freaks & Geeks, According To Jim).


01) Episode 51: “A Very, Very, Very Fine House” (Aired: 10/15/97)

Now out of jail, Drew learns his house is being put up for auction.

Written by Joey Gutierrez and Diane Burroughs | Directed by Gerry Cohen

After a nondescript and non-serialized premiere, Drew Carey‘s third season begins with a three-episode arc that contends with Mimi’s aforementioned kidnapping of Wick (in a strange story that cartoons the players too much). In the last two entries of this trilogy (both mentioned below), several other narratives are launched, including Larry’s firing, Kate and Oswald’s secret relationship, and the introduction of Nicki. As a rule, these are three story-heavy excursions, and while this last installment indeed picks up where the previous left off — in a convergence of plot that found the foursome, Nicki, and Larry arrested — I think it has the most sincere character intentions. No, not in the silly storyline involving the auction of Drew’s house (a consequence of his arrest), but in Drew’s finally having to process the information of the Kate/Oswald coupling — a development that wasn’t motivated, yet seems to exist primarily for Drew’s response, meaning that this is the moment where it first becomes of true interest to us. As a result, I like this the best of the early part of the season’s plot-laden output.

02) Episode 52: “Drew Vs. The Pig” (Aired: 10/29/97)

Drew doesn’t believe Nicki when she reveals she used to be overweight.

Written by Bob Nickman | Directed by Steve Zuckerman

Even though my above criticisms are never truly allayed — namely that Nicki doesn’t have much of a comedic personality and is instead defined only by what she can offer via the preordained plot — I appreciate the idea of Nicki being formerly overweight, and what this backstory means for both her and Drew when they’re together; it’s an explanation for her crush on him, a source of anxiety for both (given his own issues with his weight), and ultimately, a problem that will mount for as long as she’s with him. Again, the show isn’t subtle enough to keep us from knowing the ending, and this inevitability does mitigate the potency of the drama, but the fact that this arc actually has value for the Drew character, and in some ways is tailored for him, is compensatory. And because this episode is the first to explore the emotional stakes of this scenario (alongside a broad subplot with “Beer Boy” that I probably don’t like as much as others do), it’s an honest — if not hilarious — example of story trying to work for character.

03) Episode 54: “The Dog And Pony Show” (Aired: 11/12/97)

Drew and the gang stage a strip show to raise money.

Written by Deborah Oppenheimer and Robert Borden | Directed by Steve Zuckerman

This tribute to The Full Monty, broadcast during Sweeps (of course), is often regarded as a highlight of the series. I’m afraid I’m not so enamored of this outing — mainly because the show has already done so many “tributes” before (mostly in the form of musical numbers), and in this era where there are heavy narratives that could theoretically both grow and develop the characters, an entry like such simply doesn’t have the same weight (even comedically). However, it’s impossible to deny both the easy-breezy “anything can happen” sensibility — a vital part of Drew Carey’s appeal, remember — and the obvious fun the performers are having doing the strip-tease, first at the Warsaw and later in the courtroom. And although the comedy is broadened alongside this season’s norms, the episodic, jokey, and homage-y nature of the concept makes this feel closer to something that we might have seen last year. In short: it’s a difficult one not to enjoy, and there’s no doubt that it’s among the season’s most memorable.

04) Episode 58: “Vacation” (Aired: 12/17/97)

Drew has to deal with his feelings for Kate when the two win a trip to the Bahamas.

Written by Les Firestein | Directed by Gerry Cohen

Honestly, I don’t love this one. I think it isn’t among this list’s funniest and it isn’t the most satisfying — that is, I feel as if the show hasn’t mined all the possible moments from the scenario. (Again, this is probably a function of the arc not fully committing to a dramatic intent.) However, it’s one of the few offerings this year that comes close to doing so, with a story that forces Drew to directly confront his feelings for Kate and his resentment over her relationship with Oswald. Because, as we’ve noted, Drew is the most justifiable reason for the Kate/Oswald pairing, there’s something dramatically necessary and laudable when his feelings come up not for story purposes — like at the end of the year, when the show has to extricate itself from their pending nuptials — but for the purposes of exploring relationships, as is the case here. And what I like best about this one is that the characters actually talk to each other — Kate/Drew have a memorable bathtub conversation — and while it’s not as comedically or dramatically strong as it needs to be, it has the right idea. (Aside: Nicki’s overeating begins.)

05) Episode 60: “He Harassed Me, He Harassed Me Not” (Aired: 01/14/98)

Wick and Mimi plot to scam the company with a fake harassment scandal.

Written by Lona Williams | Directed by Sam Simon

My thoughts on this storyline were briefly addressed above. Frankly, the premise doesn’t seem out-of-bounds based on who we know these characters to be, but the simple fact that it is such an unpleasant idea (and I think viewers watching today will especially be repulsed by the notion of someone lying about sexual harassment allegations), and because it goes on for way too long, makes it far less enjoyable. (Also, while the show has hinted before at Mimi’s crush on Wick, since Drew and Mimi have no emotional connection, there’s not a lot of weight to her personal needs, which means we don’t care as much either.) And yet, although I have my issues with the story — or rather, the show’s decision to use it — I simply can’t ignore the hilarity of this introductory teleplay and its capacity for elevating the narrative. From Drew in the department store (with Larry), to the Scooby Doo runner, to the late-night investigation, this installment (surprisingly) has some of the year’s biggest laughs, making it a comedic gem.

06) Episode 63: “The Engagement” (Aired: 02/11/98)

Drew and Oswald take secret compatibility tests with their respective girlfriends.

Written by Bruce Rasmussen | Directed by Brian K. Roberts

Though I’ve opined that the two main romantic arcs coursing through the season work better when they’re more character-oriented and don’t have to contend with big story developments, this entry is an exception to the rule, for this one is ostensibly designed to set up the engine for the rest of the season, which is Kate and Oswald’s marriage (for the May Sweeps finale, of course). But that event has character-specific ramifications, for given Drew’s love for Kate, he can’t help but be competitive and propose to Nicki, as well… a story that, as we already know, is going to end badly (and fairly soon). Fortunately, this script manages to enliven the functionality of the premise both through character moments — and let’s note that Lewis isn’t left out of the rom-com fun, for this entry introduces his three-episode girlfriend, the delightfully strange Pinky (Ashley Gardner) — and also through a typically Drew Carey gag: an on-screen score measuring Drew and Oswald’s compatibility with their mates. Eugene Levy appears.

07) Episode 64: “Nicki’s Parents” (Aired: 02/25/98)

Drew feels responsible for breaking up Nicki’s parents.

Written by Matilda Hotkinson | Directed by Sam Simon

Barry Corbin and Anne Francis guest star as Nicki’s parents in this outing that, I admit, is of uneven merit. The A-story, where Drew goes to a fateful dinner with the pair that ends in their separation, seems to be typical sitcom fodder — helped only by the final gag where, after the friends show Mr. Fifer how “fun” the single life is, he decides to go back to his wife (once he realizes how boring they really are). What makes this one more worthwhile, though, is the subplot, in which Kate and Oswald attend counseling to discuss the intrusion of Lewis in their lives. This is a great idea for several reasons — not only does it deal with ensemble dynamics and address some of the obvious consequences of what happens in a group of four when two romantically pair, but it’s also a chance to see Kate/Oswald in a relationship-based plot that isn’t burdened by other story concerns. It doesn’t really do much to explain their coupling, but it’s the kind of material they should have been getting all season. (That’s why it’s bumped up!)

08) Episode 65: “Two Weddings And A Funeral For A Refrigerator” (Aired: 03/04/98)

Drew competes for a new refrigerator.

Written by Christy Snell and Terry Mulroy | Directed by Brian K. Roberts

One of the year’s highlights, this episodic charmer feels like classic Drew Carey. Although several of the major arcs — including the two relationships — exist here within the constructional “givens,” this excursion gives us a welcome respite from cumbersome plot. Instead, this entry is a good ol’ fashioned contest — a sort of department store Olympic Games — as Drew faces off against Mimi and Larry for a new refrigerator, which he needs now that his has broken. The game conceit is an easy sitcom device, but it typically works if the characters are gifted plenty of space within it (as they are here). Plus, there’s more of that free-wheeling quintessentially Drew Carey energy — along with a musical number (Drew and Nicki doing a take-off of “42nd Street” inside a refrigerator: an idea that addresses their season-long arc, too), a device that became overused last year but has been more judiciously featured in Three. Also, we have the second appearance of the kooky Pinky, a memorable recurring laugh-getter.

09) Episode 66: “The Bachelor Party” (Aired: 03/11/98)

Drew’s mom asks him not to reveal that he and Nicki split until after the bachelor party.

Written by Clay Graham | Directed by Brian K. Roberts

My pick for the best episode of the season, this contains one of the few legitimately dramatic moments from the entire series that doesn’t feel unearned or out-of-place — it comes at the end of the episode when Drew watches what initially began as a Drew/Nicki sex tape and then turned into their break-up tape when Nicki saw herself on camera, realized how much weight she’d gained, and blamed Drew for it. It’s a shockingly powerful moment… even though we learned in Act One that the pair has split… and even though we knew weeks ago that Nicki was gaining weight and would likely not stay with Drew much longer. You see, despite everything the show does to negate the drama of this moment, because it was more rooted in character (and their flaws) than most of what else we’ve seen this season, it still packs a punch… Meanwhile, the offering is more that just the final scene, for it’s got a really funny script that boasts the return of Drew’s parents (including Marion Ross, who’s a scene stealer — her one-on-one with Mimi may be the entry’s highlight), weaves in Drew’s recently introduced brother to include a reveal to Mr. Carey that Steve is a cross-dresser, and also addresses the pending Kate/Oswald marriage. In this regard, it’s an ideal representation of the season — its major threads, its (still) strong comedy, and its most potent form of earned character drama.

10) Episode 72: “From The Earth To The Moon” (Aired: 05/06/98)

Drew is offered a promotion… if he can make it to the boardroom in ten minutes.

Written by Christy Snell and Terry Mulroy | Directed by Gerry Cohen

As you can see, this is the only episode I’ve chosen to feature from the final quarter of the season. This is partly because the last few are bothered by the heavy story machinations of the Kate/Oswald wedding, and partly because with a total of 28 original scripts, some of these at the end feel a little tired — no matter what ideas they employ. There’s a certain truth to that observation applicable to this entry, too — it’s not an absolute gem. But it’s a low-concept idea that plays in real-time and therefore stands out among the rest of this year’s output, which has been quite reliant on story, arcs, and stunts. Here, the show is allowed to use a gimmick that doesn’t engender such stunts’ typical bigness, and the result is an entry with a more simple focus on character. Also, with its department store setting, and the fine use of Mrs. Louder (one of the show’s best recurring presences and someone we miss after she leaves the series in Season Five), this is exactly the kind of workplace show we used to see more often in the first two years… and will see far less of as time progresses. It’s unique, especially for Three.


Other notable episodes that merit mention include: the three that would have made the list had I chosen 13 (which is statistically what I could have highlighted, given that there are 28 entries) — “Strange Bedfellows” and “Misery Loves Mimi,” both of which feature Larry’s firing and the introduction of Nicki but are otherwise burdened by the unmotivated Kate/Oswald pairing and the strange Mimi/Wick story, and the closest to the list, “Batmobile,” a memorable Sweeps entry in which Drew wins the Batmobile… Now, because of the high episode count, I’m also including a complete section of Honorable Mentions: “The Brother,” a decently written show that introduces John Carroll Lynch as Drew’s cross-dressing brother but suffers from the same thing most Steve Carey episodes do — his lack of definition beyond the transvestism, “That Thing You Do,” a very Sweepsy offering featuring Seth Green and The Reverend Horton Heat that has some nice camaraderie among the core four, despite a one-joke premise, “The Salon,” which utilizes Mrs. Louder to fine effect, and “The Sex Drug,” which concludes the Mimi/Wick lawsuit and attempts to dovetail a subplot into the court case as a means of comedic conflict (but with only a modicum of success).


*** The MVE Award for the Best Episode from Season Three of The Drew Carey Show goes to…

“The Bachelor Party”



Come back next week for Season Four! Stay tuned tomorrow for a new Wildcard Wednesday!

2 thoughts on “The Ten Best THE DREW CAREY SHOW Episodes of Season Three

  1. never understood kate and oswald together . but i like the finale wedding ep becuase it makes me laugh . what do u think of that one ?

    • Hi, BB! Thanks for reading and commenting.

      I like some of the moments with Adrienne Barbeau as Oswald’s mom, but I think the episode is centered around a story development that it simply can’t motivate through believable character strokes.

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