The Ten Best THE DREW CAREY SHOW Episodes of Season Four

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.

Something you’ll notice immediately about Season Four, the first without creator Bruce Helford’s undivided attention (thanks, Norm), is the writing’s increased broadness. You’ll see the evolved sensibility in gags, like the premiere’s subplot with Mimi and the “mood” make-up that changes color with her emotions; in A-stories, like in the popular “DrugCo” episode where the show finally ventures down to Lewis’ notorious workplace; and in whole arcs, like the storyline where Oswald gets breasts. (Yes, breasts.) Speaking of arcs… they’re all smaller than those employed in Season Three, which was notable for its heavier story interests. Some of this year’s most memorable multi-episode narratives include: Drew starting a band, Mimi having an affair with a married guy, Wick going to rehab for drug addiction, the company trying to buy Drew’s house, Drew dating an older woman (Shirley Jones), Drew competing with both Lewis and Oswald for the affections of a girlfriend (Diane Farr), and Drew finally winning over his handywoman crush, Sharon (Jenica Bergere). But not all of these arcs are created equal. For instance, the first three stories in the above list — all of which come within the year’s first two months — aren’t great. As we discussed a bit last week, personal arcs with professional characters like Mimi and Wick tend to be less satisfying because Drew’s emotional interests are nil; we care less about what they want when Drew doesn’t. Additionally, and this is also the case with the gimmicky storyline where Drew launches the hotel house band, the Horn Dogs (in an arc that includes Joe Walsh and Pauley Perrette), these ideas don’t make great use of anyone but the one regular at the center. They’re more contained, with little ensemble interaction, and thus, lower emotional stakes and less character-based comedy. Meanwhile, the middle story — where Winfred-Louder purchases Drew’s neighborhood — seems to be the ideal blending of the premise’s personal and the professional, but it’s “schmuck bait” (story for story’s sake — we’re merely waiting for the status quo to return), and there’s no reason to emotionally invest.

In contrast, the latter three stories in the above list — all of which, in some way, involve Drew’s dating life — tend to be more successful, for they’re better at incorporating the other characters, particularly Drew’s core four friend group. There’s still a certain level of gimmickry here — note the casting stunt with Shirley Jones, who, in one episode highlighted below, also interacts with another ‘70s TV mom (Marion Ross) — but they’re simply better for the show as it’s designed. Additionally, the stories dealing with Drew’s love life this season serve as a welcome contrast to the heavy-handed (though somewhat successful) narrative pursuits of the year prior, and the casualness with which these arcs progress is more appealing. Case in point: Sharon, who was introduced last season but doesn’t finally become Drew’s girlfriend until a whole calendar year later. Season Four brings her in every so often to remind us of her existence, but it waits a while before actually pairing her with Drew. As a result, by the time they unite, we’re more invested — not because the story is begging us to, but because the telling has delayed Drew’s gratification, making us more amenable to rooting for them (even though, as I always say with Drew’s love interests, she isn’t as well defined comedically as I’d like). I prefer this; there’s more room now, theoretically, for character and comedy… However, if there’s one drawback to the change in narrative styles between Three and Four, it’s that in moving away from the prior’s heavier emotional plots, this year negates the relationship between Oswald and Kate. After the season premiere, the show goes forward almost as if the whole thing never happened. Because of this, one feels like it didn’t need to happen — neither character has grown or changed because of it. In this way, Season Four makes Three, with hindsight, look less valuable…

On the other hand, Three compares favorably to Four because of some things we’ve already discussed: the broadening, the gimmickry, and, as we’ve been tracking, the disparity that’s growing between the personal and the professional. We mentioned some examples of broadening above, but I have to explain why it’s a problem. You see, this show was never adherent to typical “realism,” but it nevertheless began much more relatably, and as it continues to rely on more extreme sources of comedy — not to mention gimmicks (like Shirley Jones’ casting, the cameos by musicians who audition for Drew’s band, and the terrible on-location episode where Mimi ships Drew to China — it’s bad, y’all) — the characters are undermined, along with our faith in them… As for the shifting balance in the premise between the home and the office, it must be known that Four still has strong A-stories set at work (the finale is a great example), and there are, in particular, some memorable episodes with the delightful Mrs. Louder. It’s not ‘til next year that the figurative scales are truly tipped. However, a direct comparison between Four and say, the Golden Age of Season Two, which was golden for how it used both facets of its structural premise, reveals the direction into which the show is heading, for every arc is personal, even those with Mimi. Her romance with Steve Carey, Drew’s brother, is Exhibit A… Although Steve lacks color (he’s defined only by his transvestitism), this arc’s impulse to bridge Drew’s worlds is smart and thesis-connected, and because it plays to the most comedic relationship — Drew/Mimi — it suggests a lot of laughs. Also, it’s a Mimi storyline about which we care; not because we care about Steve (or even Drew’s relationship with Steve), but because we care about the Drew/Mimi dynamic, as that’s been so comedically generous… And yet, the trend is reinforced: it’s still more weighted on the home front, and as we’ll see soon, when Drew/Kate arise, we’re careening to a less-than-ideal standard. Here in Four? The show hasn’t yet cut itself off from its halcyon days, but they’ve definitely passed… So, on that note, I have picked ten episodes that I think exemplify the season’s strongest.

This year’s writers include: Clay Graham (Benson, Who’s The Boss?, Anger Management), Joey Gutierrez (Martin, Raising Hope, Last Man Standing) & Diane Burroughs (Martin, Yes Dear, Still Standing), Richard Day (Ellen, Mad About You, Larry Sanders, Spin City, Arrested Development), Jennifer Crittenden (Simpsons, Seinfeld, Raymond, Veep), Brian Scully (Out Of This World, Simpsons, Family Guy), Dan O’Keefe (Seinfeld, The League, Silicon Valley), Mike Larsen (Ellen, Two Guys & A Girl, Whoopi), Christy Snell, and Terry Mulroy (According To Jim, Still Standing, Outsourced).


01) Episode 75: “Drew And The Conspiracy” (Aired: 09/23/98)

Drew finds out that some of the employees are conspiring against him.

Teleplay by Jennifer Crittenden | Story by Bob Underwood | Directed by Gerry Cohen

Season Four opens and closes with workplace A-stories, bookending a year that, like its two surrounding, actually moves the show further and further away from the professional realm as personal stories dominate. This entry indicates the latter, introducing a mini-arc for Mimi in which she falls for a guy who is married. Additionally, some of the seasonal trends we discussed above are evidenced — the immediate uptick in broadening (witnessed by Mimi’s color-changing make-up) and the character-destroying negation of the previous year’s emotional arcs (via the brief, tidy way that the Kate/Oswald aftermath is handled). As for the A-story, it’s funny and features appearances from Kevin McDonald, Kevin Weisman, and Tracy Letts.

02) Episode 77: “Golden Boy” (Aired: 10/07/98)

Drew dyes his hair and tests the employees for drugs.

Written by Bruce Rasmussen | Directed by Gerry Cohen

With several of the year’s early narratives weaving through it — including Drew’s hotel rock band (which features the aforementioned guest stars, Walsh and Perrette), Mimi’s affair with a married man (Gregory Jbara), and Wick’s cocaine problem, which sends him into rehab at the top of the following entry — this is a script that could very easily be overcome by its stories. Fortunately, the teleplay — one of two this year credited to Rasmussen — is plot-elevating, and the A-story, where Drew has to get urine samples from all the employees, is another workplace gem that makes time for many of the office’s peripheral players (including “long time, no see” veterans like Nora), representing a unique professional story from Season Four.

03) Episode 79: “Sexual Perversity In Cleveland” (Aired: 10/21/98)

Drew and Mimi unknowingly start a relationship over the internet.

Written by Mike Larsen | Directed by Gerry Cohen

There’s no doubt about it: this is a Victory in Premise that would be featured on this list (or at least the Honorable Mentions) no matter what, for the very idea of Drew and Mimi doing the digital You’ve Got Mail version of the ol’ The Shop Around The Corner pen pal routine is inherently comedic given what we know of them and their relationship. This capable script maybe doesn’t reach the heights of hilarity that the series has been able to meet in its less traditional, more “anything can happen” ideas, but it doesn’t let the premise down either, and it wrings as many laughs as can be expected from the scenario. Also, the mini-arc about Oswald getting breast implants to raise money for his mom begins, hilariously, here. It’s a riot — broad, but a riot.

04) Episode 87: “Drew’s Holiday Punch” (Aired: 12/16/98)

Drew introduces Celia to his parents on Christmas.

Written by Jennifer Crittenden | Directed by Gerry Cohen

As the middle part of the three-episode arc in which Drew dates a senior citizen, played by Shirley Jones (best known, of course, from The Partridge Family), this is undoubtedly one of the season’s gimmickiest, for all the sincere character interests that could be produced as a result of this storyline are mitigated by additional casting stunts — not only the already-stunty inclusion of another classic TV mom, Marion Ross (who appears here with Stanley Anderson as Drew’s dad), but also in the decision to have Partridge Family alum Danny Bonaduce play Celia’s son. A metatheatrical wink has never been beneath this series, yet it doesn’t help the characters either… And yet, with all that noted, this is the funniest of the Celia arc because of the interactions among the family members, and it’s the only time that the “Drew dates a senior” narrative truly reaches its comic potential. (It’s definitely the most memorable, too!)

05) Episode 90: “Rats, Kate’s Dating A Wrestler” (Aired: 01/27/99)

The group hires a wrestler to be the spokesman for Buzz Beer.

Written by Christy Snell and Terry Mulroy | Directed by Steve Zuckerman

This seemingly well-liked episode isn’t one of my favorites — I’m not wowed by the casting of wrestler Triple H; it’s another stunt that doesn’t spark any extra character-driven comedy. However, what I like about this entry is the screen time it affords to our core four, a group that still works well together, gets big laughs, and earns our emotional trust, even though it hasn’t really evolved in ways that would make it more conducive to story. (This is because the Kate/Oswald pairing has effectively been discarded and treated as if it’s never happened, limiting all their emotional truths.) Also, this is another case where the teleplay is capable of elevating the narrative — it makes time for character and remains consistently amusing.

06) Episode 93: “Tracy Bowl” (Aired: 02/24/99)

Drew, Lewis, and Oswald compete for Tracy’s affections.

Written by Robert Borden | Directed by Sam Simon

Even this, one of the season’s most inventive and enjoyable outings, isn’t immune to the broad gimmickry of its heightened era. Concluding the three-part storyline where Lewis, Oswald, and Drew all vie for the affections of Tracy (Diane Farr) — the first two Tracy shows are mentioned below — this entry spices up the proceedings with a competition structure that isn’t necessarily novel, for we’ve seen it before (like in last year’s “The Engagement”), but is dressed up by cameos from sportscasters Bob Costas, Kenny Mayne, and Lynn Swann, who appear as themselves and give commentary on the competition. There’s a certain fun quality and Golden Age Drew Carey wildness to this gag that keeps it from being annoying (as most of the rote casting stunts are). But even without this heightened conceit, the excursion would be a classic, for Carey, Bader, and Stiles shine in what is probably one of their finest showcases ever.

07) Episode 95: “Steve And Mimi” (Aired: 03/24/99)

Drew is shocked when Steve and Mimi start dating.

Written by Bruce Rasmussen | Directed by Gerry Cohen

Yes, this is the one where the series finds a more permanent way to connect Drew’s home life with his work, as Mimi begins a relationship with Steve — a development that’s not only going to increase the appearances of John Carroll Lynch, but will also help pivot the show away from the office in a more obvious, aggressive manner. My thoughts on this decision were discussed above, yet I have to commend this particular episode for disguising the narrative’s structural functionality not, as it usually happens, through broad outrageous comedy, but in a form of character-reverent humanity that seeks to explain the connection between Mimi and the nevertheless nebulously defined Steve. It’s treated genuinely… which both makes the story believable and helps make the laughs pop. An MVE contender (credited to Rasmussen).

08) Episode 97: “She’s Gotta Have It” (Aired: 04/07/99)

Sharon wants a sex-only relationship with Drew.

Written by Apryl Huntzinger | Directed by Tommy Thompson

Frankly, I wish this was funnier. Given just how broad and heightened the baseline is this season, one expects a certain type — and volume — of comedy from its output, and this one maybe doesn’t excel in the way that a, say, “Tracy Bowl” does. However, as with the above “Steve and Mimi,” this is an episode with a surprisingly character-centric humanity, stemming from the thoughtful and deliberately casual manner with which the show has included and progressed the Sharon storyline. Although she, like many of the show’s love interests, isn’t as well-defined as I’d like, her pop-in appearances have increased her comfort level with Drew, so that by this time, they have a good chemistry and we’re rooting for them. This, coupled with the funny idea of Drew wanting a relationship but being used only for sex, makes for a winning installment. Also, Whose Line‘s Colin Mochrie guests in the subplot.

09) Episode 98: “Good Vibrations” (Aired: 05/05/99)

Someone puts a vibrator in Drew’s luggage.

Teleplay by Mike Larsen and Dan O’Keefe | Story by Terry Mulroy | Directed by Brian K. Roberts

In contrast to the above, this is an outing with a Victory In Premise that has no shortage of laughs, but certainly won’t be commended for its character-rooted humanity. Oh sure, there’s something to be said for Sharon’s desire to be part of the gang and the deepening bond between her and Drew, but let’s face it — the appeal here is the outrageously funny idea on which it’s predicated: that someone slips a vibrator into Drew’s luggage before the security line at the airport, making him the laughing stock at a convention. It’s my MVE and, yes, I’m a little surprised; surely, my “refined” tastes would prefer the humane to the ribald. But I simply don’t think any other entry this year is as memorable or as evocative of that early Drew Carey “anything goes” charm. I can’t deny it. All the jokes we expect are there and the script doesn’t disappoint. Also, it’s smart that the show wastes little time in revealing the culprit of the prank, for while Drew is led to believe (naturally) that it’s Mimi, who provides some of the best laughs with her delight at his humiliation, the audience is pretty sure it’s the prank-lovin’ friend group, and so when Sharon confirms it was her, the show is crediting our intelligence by not dragging out the reveal. Additionally, this represents a perfect balance of the personal and the professional — which, as we know, is key to the series’ peak functioning.

10) Episode 101: “Brotherhood Of Man” (Aired: 05/26/99)

Drew learns that there’s a plot to destroy the company.

Written by Brian Scully | Directed by Gerry Cohen

Bringing us full circle — with an episodic workplace story — this season’s finale, guest starring Hal Linden (of Barney Miller), stands at what looks to be a unique precipice, where the show is still tethered, somewhat uncomfortably, to the past, yet is no longer capable of being as enjoyable… and therefore will evolve into its future, out of necessity, but certainly also to its further detriment. You see, as we’ve explored, next year will officially disrupt the well-modulated balance between the two main parts of the show’s structural identity: the home and the office. And so an episode like this, all workplace, seems to be among a dying breed. Additionally, the installment’s climax — a musical number (“Brotherhood Of Man” from How To Succeed In Business Without Really Trying) — is a vestige of an earlier era, a throwback to the time (Season Two) when this oft-repeated gimmick was a legitimate signal of the series’ freshness, and not, as it is here, its lack of creativity. Much has changed, but more is coming…


Other notable episodes that merit mention include: the closest to the above list, “Drew’s New Car,” which has some sweet-but-comedic interplay among the core four and then an appreciated bridge to the office via Drew’s combative dynamic with Mimi, the well-liked “In Ramada Da Vida,” which introduces the band arc and is excessively overpraised because of its roster of rocker cameos, and the first two parts of the Tracy trilogy (“Three Guys, A Girl, And A B-Story” and “Boy Party/Girl Party”). Of more Honorable Mention quality are the previously discussed “DrugCo,” which is way too broad for my liking (but for which guest Charles Nelson Reilly, in his second show as Lewis’ boss, earned an Emmy nod), “Do The Hustle,” which starts smartly but devolves into a story that never quite rewards us, and “Up On The Roof,” which doesn’t take advantage of its premise’s comic potential.


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

“Good Vibrations”



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