The Ten Best THE DREW CAREY SHOW Episodes of Season Two

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.

The second season of The Drew Carey Show is the strongest by the metrics we established last week — it has the most ideal balance between Drew’s home life (featuring a Midwestern “Singles In The City” group of friends) and the office (featuring the lead’s core antagonist), with a spontaneous “anything can happen” sensibility that is well-supported by both a simple understanding of character and stories that actually reflect their definitions. As we’ll soon see, Season Three can boast similar claims, and indeed, if there’s any other year in contention for the series’ finest, it would be that one. However, Three has grander story concerns that miss a little more often than Two’s self-contained episodic (or two-part episodic) silliness. Also, this year benefits from the same ol’ thing we’ve seen time and again on this blog: the sophomore blessing of novelty meeting knowingness — when the show and the audience knows what to expect from character, but can still be surprised from story (and the telling)… Yet I say that not to undermine Two’s unique strengths — specifically, the things it does to ensure its own success, for there are smart decisions made on both the personal and professional fronts. At home and with the core four, the natural choice to exploit the prior finale’s introduction of Buzz Beer is astute — for it’s a terrific way to keep the friend group in tact for weekly story while also being a symbol of the series’ relatable “blue collar” vibes (which help keep the “Singles In The City” trappings original and not overtly derivative). Plus, with Drew and Kate quickly extricated within the first month from their first season romances — with Lisa and Jay, respectively — the show has more room to explore dating stories with its leads. Drew is now freer than ever before.

And his freedom matches the series’ — again, anything can happen. This energy is vital to its peak functioning — and that’s something that, as we know, was implanted from “go.” You see, unlike NewsRadioThe Drew Carey Show isn’t contained in a metaphorical box — it’s got places to be. Even the office, which is the other half of the show’s constructional premise and something that must also be reinforced weekly (note: one of the concerns we’ll observe going forward is the gradual de-emphasizing of the workplace), doesn’t act as a narrative inhibitor. Thanks to this show’s comedic sensibilities and its loose characters, the cubicle — forever a metaphor for literal confinement — isn’t restrictive. It’s merely a pressurizer for more slap-happy, feel-good, rule-breaking insanity, and unlike NewsRadio, which was unfortunately trapped by its figurative workplace box, Drew‘s structure serves as an anchoring device that helps contextualize the broadness and keep the show from cutting itself off from “reality” — that is, the version of “reality” that exists within established depictions of sketch-like but investment-worthy characters, such as Drew and Mimi. But those two aren’t all the office has to offer, and the aforementioned good decision that Two makes at work is the introduction of an additional oppositional force — for both Drew and Mimi — in the form of Craig Ferguson as Mr. Wick. Although his character will become one of the series’ broadest, the simple inclusion of a physical obstacle — as opposed to the off-screen menace of Mr. Bell — provides more by way of story and comedy. Additionally, the further use of employees and employers — like Mrs. Louder, who appears in a few memorable outings here and will find her usage increased exponentially next season — helps build the world of Drew’s workplace, which is as fertile as (if not more than) Drew’s home, where he also sees funny folks with whom he has strong bonds and great chemistry. You see, wherever Drew goes this year, there’s opportunity.

Are there signs of trouble ahead? Well, with the show realizing that its comedic identity doesn’t make much room for über-serious dramatics (the kind tried a bit in the first half of last year), the characterizations never graduate beyond their simplistic definitions. The premise’s structure doesn’t compromise or force the issue weekly in the quest for story (like NewsRadio‘s did, for instance) but this year is already aggressive in its obedience to network TV’s commercialism. When there are palpable stunts (and Two has a surprising many) — specifically casting gimmicks timed for Sweeps — it’s hard to ignore the shallow nature of the characters in relation. But while this may be annoying, and other gimmicks — like the show’s use of musical numbers — are starting to become overused by the end of the season, the novelty inherent to the year keeps us afloat. In fact, there’s little reason to complain — then or now — for the show was the biggest hit of the Alphabet Network’s B-comedy block (Wednesday). To wit, when the brass realized that Drew Carey at 9:30 was doing better than its 9:00 anchor (Grace Under Fire), they did some reshuffling, putting the night’s most-watched sitcom at 9:00 up against NBC’s own Workplace effort — yes, NewsRadio, then also in what I’ve deemed its finest season. Head-to-head, viewers much preferred Drew Carey, and though this is certainly most attributable to the differences between the two blocks — good neighbors is of huge value — it’s not difficult to see why Drew Carey was so popular. It’s easy. It’s unbound. And unlike NewsRadio, it’s optimistic — it breaks rules for fun, not for necessity or reputation. So, with seemingly limitless possibilities, The Drew Carey Show’s second season is one of the decade’s most exciting. And as usual, I have picked ten episodes that I think exemplify the year’s finest.

Notable writers this year include: Bruce Helford (Roseanne, Norm, George Lopez, Anger Management), Clay Graham (Benson, Who’s The Boss?), Robert Borden (Pride & Joy, The Brian Benben Show, Late Show With David Letterman)Joey Gutierrez (Martin, Raising Hope, Last Man Standing) & Diane Burroughs (Martin, Yes Dear, Still Standing) and Lona Williams.


01) Episode 23: “We’ll Remember Always, Evaluation Day” (Aired: 09/18/96)

Drew has to evaluate the employees — including Lisa.

Written by Les Firestein | Directed by Brian K. Roberts

Season Two’s premiere is maybe the most reminiscent of the year prior, for the great workplace premise, which takes advantage of Drew’s job and the conflict it presents for him personally with Lisa, serves as the A-story. This isn’t necessarily a selling point for this list though — Lisa has always been shakily defined and, with hindsight, we know the show is better when it cuts Drew loose. However, the office setting is fertile territory for some great Drew/Mimi bantering and the reason this entry makes the list — aside from the opening “Five O’Clock World” number (the first of several great song-and-dance moments this year) — is the prank war between the two. As a reintroduction to their relationship, this B-plot may actually be the best distillation of their dynamic (and the comedic opportunities it provides). Ideal start to Season Two.

02) Episode 27: “The Devil, You Say” (Aired: 10/30/96)

Kate starts to date a guy who claims he is “The Devil.”

Written by Bruce Helford | Directed by Sam Simon

Grant Shaud, fresh off eight years on Murphy Brown, guest stars in this episode, which boasts a unique premise (somewhat Halloween inspired — there’s a memorable sight gag where Drew dresses up as Mimi for the holiday) and a lot of laughs. While the idea of Kate dating the devil — or someone who thinks he’s the devil — seems, on paper, a little too dark and hocus pocusy for a flippant series that’s still relatable (if not “realistic”)… the strong script plays into the show’s off-kilter sensibilities without forsaking the tonal identity that might get lost in the noise. It, interestingly, allows the danger of “the Devil” to play unmitigated though, and that seems especially (and welcomingly) bold. In fact, the sheer audacity of the concept, and the fact that the humor is so strong, helps overcome its typically unappealing high-conceptness.

03) Episode 28: “The Day The Music Died” (Aired: 11/06/96)

Drew is sad to learn his high school music teacher died.

Written by Robert Borden | Directed by Gerry Cohen

We’ve seen variations on this theme before on other shows — either the death of an old teacher who influenced the life of a student, or the revelation of a past romantic/sexual tryst between professor and pupil. Narratively, this installment doesn’t bring much to the table — and it’s certainly not as unique as the above — but it’s here because it’s actually a good ensemble showcase for the core four friend group. The constructional decision to have them all be old childhood pals gives them a shared history that can be routinely mined for story (and comedic moments), and in this case, that definitely adds to the plot — while also providing an interesting tidbit: Oswald and Kate were each other’s “first.” (This is a fascinating precursor, and perhaps an explanation, for their misbegotten relationship; more thoughts soon…)

04) Episode 32: “It’s Your Party And I’ll Crash If I Want To” (Aired: 12/04/96)

Drew and Mimi both find themselves excluded from a party.

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

As with last season’s classic “Drew And Mr. Bell’s Nephew,” this strong excursion — a candidate for MVE — contends with an unholy alliance between the series’ perennial nemeses: Drew and Mimi. The inversion of the anticipated — here, their decision to put aside their bickering (somewhat) to join forces against a common enemy, whom they believe has purposely excluded them from a party — is always a great source of laughs, and it’s appreciated because it’s reliant on an institutional knowledge of the characters and their relationships. In some ways, this might seem a bit easy, but for Drew Carey, it’s, frankly, a great indication of the writing doing what it needs to do with the regulars (based on the way they’ve been defined).

05) Episode 34: “They’re Back” (Aired: 01/08/97)

Drew’s parents return and take back their house.

Written by Clay Graham and Robert Borden | Directed by Brian K. Roberts

Stanley Anderson, who appeared last season in a heavier-than-usual outing, returns here alongside Marion Ross (best known as the matriarch from Happy Days) as Drew’s parents. This two-part story finds the pair reclaiming their house, thus putting Drew in the awkward position of living with his folks again. One of just a few mini-arcs from the second season — another notable one being where Drew dates a zoning inspector, played by Caroline Rhea — both of these entries are improved by Ross, for although her casting is a gimmick that I typically can’t stand (and Happy Days isn’t high on my list of shows to subliminally reference), she brings a spark to the proceedings that actually fits right in with the “anything can happen” energy. This entry, in particular, is loose and fun — there’s the story, sure, but that’s not why we’re watching.

06) Episode 35: “Hello/Goodbye” (Aired: 01/15/97)

Drew gets Lewis and Oswald kicked out of their apartment.

Written by Susan Garon | Directed by Gary Halvorson

Although the spontaneity and quintessentially Drew Carey joie de vivre isn’t as evident in this installment as it is in the above, this one secures more of its points by being great for the characters — particularly our core four. It’s, no surprise, great fun when Drew decides to leave his parents’ house and move in with Oswald and Lewis, the latter of whom, in a jokey subplot, is dating Mr. Bell’s old assistant/mistress Suzie (who’s now footing the bill for Lewis’ adult braces). Then, after Drew gets the trio evicted — by the landlord (He & She‘s Kenneth Mars) — they’re forced to bunk with Kate: a classic ensemble scenario. And while most of the episodes this year are strong, few are as strongly designed. It’s a solid episode from a solid year.

07) Episode 37: “Drew Blows His Promotion” (Aired: 02/05/97)

Kate plays a prank on Drew during his bid to earn a promotion.

Written by Susan Dickes, Christy Snell, and Robert Borden | Directed by Sam Simon

Perhaps one of the most memorable installments from the series’ entire run — rivaled, I’d argue, by the episode that I’ve chosen to highlight as my pick for the season’s finest — this MVE runner-up is an excellent workplace-based outing that ably melds Drew’s life at home with his life at the office. While Drew makes a video on harassment in the workplace (which is funny enough) in a bid for a promotion (from Mrs. Louder, who’s back — thank goodness!), the core four’s character-rooted habit for pranking one another yields a classic sitcom conflict where a gag tape is accidentally switched with the correct one. The gag tape — doctored by Kate — is overloaded with fart noises, a juvenile source of comedy… but one that few American sitcoms would be bold enough to commit to as a primary punchline (especially when combined with the gastrointestinal issues that plague Drew in the climax). A favorite — unique and unapologetic.

08) Episode 41: “Man’s Best Same Sex Companion” (Aired: 03/05/97)

Drew pretends to be gay to get the company to cover the insurance for Speedy’s surgery.

Written by Joey Gutierrez and Diane Burroughs | Directed by Robert Borden

This is another one that won’t win points for narrative originality — how many shows have we seen employ a story where one character pretends to be gay and recruits his/her friend to help support the ruse? (Too many to count!) It’s sort of a Victory In Premise, for the farcical possibilities of characters we know performing different personas are always great. But this entry seems to know this is typical sitcom fodder and it sneaks in surprises while not denying some of the anticipated beats. For example, we expect a gag like Drew and Oswald coming up with different answers to questions about their relationship, but we’re not expecting the final beat that — spoiler alert — convinces the board (and Mrs. Louder) of their sincerity. In this way, The Drew Carey Show supports the sitcom as we know it, but maintains its originality.

09) Episode 45: “Win A Date With Kate” (Aired: 05/07/97)

Wick wins a promotional date with Kate and they begin a relationship.

Written by Joey Gutierrez and Diane Burroughs | Directed by Steve Zuckerman

Regular readers know I’m not usually a fan of entries that base their stories in elaborate schemes — I think the gag often overrides the character moments, for whether or not we’re “in” initially on the plot, we’re distracted: either by the story or by the ultimate negation of it. Additionally, given what hindsight will tell us about Drew Carey‘s problems with the coupling of its regular cast members, an episode like this — where Kate and Mr. Wick turn into an item — seems to be skating on thin ice. However, because this comes before any of the sincere Kate pairings, and because the scheme itself (and the second one) are less about the comedy of the plot and more about how the character dynamics change as a result of them, I’m able to enjoy the laughs, and specifically, the character beats that propel them. (Yet this is one that only works in Two.) Trivially, I’d also like to note that this was originally broadcast by ABC in 3-D.

10) Episode 46: “New York And Queens” (Aired: 05/14/97)

Drew and his crew take a spontaneous trip to New York City.

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

There are reasons to not like this episode. The single-cam non-audience scenes clearly miss the energy provided by the multi-cam format. Also, the big climactic centerpiece — yes, this is the outing that contains one of the series’ most memorable moments, the battle between “The Time Warp” from The Rocky Horror Picture Show and “Shake Your Groove Thing” from The Adventures Of Priscilla, Queen Of The Desert — already feels a bit played-out, given the sheer number of musical numbers that Season Two has already offered. However, the low-concept simple character interplay (enlivened, okay, by some May Sweeps-y cameos, including ones from Donald Trump and Carol Channing) saves the text. And the boldness of the musical battle — a nice bookend to a year that began with a song-and-dance — mitigates any concerns we might have about the use of gimmicks. Instead, we’re able to appreciate this as an honest look at what The Drew Carey Show has been able to do this year. For its sheer unforgettability (I don’t think any other episode this year comes close; although all the musical numbers, like “What Is Hip?” — mentioned below — are seminal in their own rights), this is my MVE: the looniest, most uninhibited situation comedy on network TV in ’97, and the only show that would think to end a season with a tribute to two of pop culture’s campiest cult classics. Perhaps The Drew Carey Show is saying something here about how it wants to be remembered, too…


Other notable episodes that merit mention include: the aforementioned two-parter with Caroline Rhea as a married zoning instructor who dates Drew, “What The Zoning Inspector Saw” and “Drew’s The Other Man,” the latter of which also includes the iconic “What Is Hip?” opening and an amusing subplot with Oswald (it was the CLOSEST to making the above list), and “Drew Vs. Mimi, Part II,” which features Mrs. Louder in another memorable workplace competition storyline. There are a lot of other entries that could be Honorably Mentioned here, but to save space, I’ll name “Two Drews And The Queen Of Poland Walk Into A Bar,” which features the return of David Cross’ Earl, who’s now obsessed with Drew, and note that I like the ice cream truck scene in “Cap-Beer-Cino,” the first half of “See Drew Run,” and some of the absurdity of “Mimi’s Day Parade.” 


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

“New York And Queens”



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

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