The Ten Best THE DREW CAREY SHOW Episodes of Season Five

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. JOHN CARROLL LYNCH recurs as Steve Carey.

Season Five of The Drew Carey Show is a year we’ve been anticipating for weeks, for with its decision to romantically pair Drew and Kate, it symbolically caps a trend that we’ve been tracking since the Golden Age: the implosion of the premise’s balanced work/home structure in favor of a more obvious emphasis on personal non-office stories. Evidence of this shift can also be found in the marriage of Mimi and Steve Carey — which we talked about last week — although the primary ambassador for this changing tide is definitely the relationship between Drew and Kate, which guides popular perception of the season. (If you are in favor of the pairing, you’ll like this year; if not, you won’t.) Personally, I have mixed feelings, for as we noted with Kate/Oswald back in Season Three, the series established Drew’s feelings for the group’s token female very early on and set certain expectations: if ever Kate was to become involved with a regular, it would be Drew. Thus, when Kate started dating Oswald — a storyline that didn’t arise organically and didn’t end organically either — the only way we could justify its existence was to presume that it would lead, finally, to Drew/Kate. When that didn’t happen, the whole arc lost credibility… some of which was further eroded in Season Four when the show didn’t properly handle the emotional ramifications of the development, instead sweeping them under the rug. Here in Five, the show has the chance to make more mention of Kate/Oswald — and it does so, casually — but the baggage is a little greater than the series wants to pretend, for just as with Friends, repeated couplings within a contained group become less and less believable. In this way, Drew and Kate’s fifth season pairing is a battle between intention and actuality. If we choose to leap along with the arc — even though it, like Kate/Oswald, doesn’t start believably (Kate’s turn is poorly motivated) — we’re doing so only out of loyalty to the sincerity of that first season’s character projections and not because Five earns it.

You see, the year’s treatment of Drew/Kate isn’t commendable. Not only are Kate’s feelings for him sparked by very little, but the season chooses to drag out its progression for Sweeps (just like Friends), contriving reasons for Drew to not learn about her feelings until November, not intend to consummate their relationship until February, and not actually consummate their relationship until May. This strain in the plotting doesn’t help the inlaid emotional motivation problems, and again, it’s only because of our favor for the series — and what it long ago said it wanted — that we decide to be more forgiving. Also, I’m less critical because it seems the fifth season’s plans for the couple were captive to Christa Miller’s pregnancy, which forced strict usage of Kate (lots of sitting or lying down scenes)… and, interestingly, likely contributed to the year making one noble, final push to revitalize the office and keep the workplace engaged in story, as it tries to develop a new recurring character in the form of a Mrs. Louder replacement, Mr. Soulard (Mark Curry), who takes over after the company decides to combat a racial scandal by diversifying its board. But if the show was feeling hamstringed and burnt out with the office the way it was, Soulard’s comedically one-note depiction isn’t an improvement, and he only appears in six episodes — during which the show enacts another brief arc meant to give the workplace a jolt: Drew taking Mr. Wick’s job… Sadly, not much comes from this new dynamic either, although, admittedly, it isn’t explored for very long; four episodes later, the status quo has returned: it’s back to business as usual. And while there are clearly efforts made in Season Five to keep the office a vital part of the series’ identity (like the addition of a “Mini Mimi”), the things thrown at the wall here — by and large — aren’t outstanding, and the year gives up almost as soon as it’s begun. If I had to pinpoint the problem, it’s that the show isn’t cultivating (and has neglected to maintain) a deep bench of colorful recurring players — you know, like it used to have with folks like Larry (Ian Gomez, who Helford snapped up for Norm). As a result, Season Five is where Winfred-Louder really stops being important.

This feeling that Season Five is the end of an era is something that’ll probably become clearer next week when we discuss Six, which, spoiler alert, has a reduced episodic success rate. Yes, Five is still fairly good on this front — there are outings that clearly miss the mark, but the good majority of them have something recommendable, and if you’re asking me where I’d draw a figurative line in terms of the series’ trajectory and its enjoyability, I’d still include The Drew Carey Show’s fifth season on the good side… That’s not to say, though, that there aren’t troubles. Once again and as usual, the show’s reputation for “anything can happen” gimmickry becomes harder to maintain as the series progresses, and this year seems particularly desperate with its gimmicks — we’ve got fewer by way of story (and casting), but more by way of the actual episodic stunts, like the third edition of the “What’s Wrong With This Episode?” foolishness (which are always lacking — that’s why the game is added on top), the first of the show’s live semi-improv’d outings (which play to the performers’ strengths but never reach promised heights), and the season’s finale, “A Very Special Drew,” in which the series metatheatrically mocks itself by shoehorning in a bunch of dramatic clichés in “a bid to win an Emmy.” That last one, something we’ve never seen before, is hilarious — a genuine example of the show thinking outside the box and affirming the freewheeling part of its identity. But, you’ll notice, it’s independent of character… and there’s no getting around it: character is the guiding force for comedic success and failure in the sitcom, and as the show moves further away from consistent, viable characterizations, it also moves further away from its best days. Things aren’t BAD yet, but the clock of baseline enjoyment is, well, it’s running down… So, on that happy note, I have picked ten episodes that I think exemplify the year’s strongest.

This year’s writers include: Clay Graham (Benson, Who’s The Boss?, Anger Management)Robert Borden (Pride & Joy, The Brian Benben Show, The Late Show With David Letterman), Holly Hester (Ellen, Grace Under Fire, Sabrina The Teenage Witch), Linda Teverbaugh & Mike Teverbaugh (Who’s The Boss?, Roc, Last Man Standing), Brian Scully (Out Of This World, The Simpsons, Family Guy), Dan O’Keefe (Seinfeld, The League, Silicon Valley), Terry Mulroy (According To Jim, Still Standing, Outsourced), and Mitch Hunter & Jana Hunter (According To Jim, The Middle).


01) Episode 104: “Drew And The Gang Law” (Aired: 10/06/99)

A judge rules that the foursome is a gang and must separate.

Written by Dan O’Keefe | Directed by Gerry Cohen

Following two episodes — including one with on-location portions shot in Cleveland — designed to extricate Drew from Sharon, the year’s third excursion is its seasonal highlight (and my MVE). It’s an ensemble showcase dedicated to the core four friend group that utilizes their involvement in Buzz Beer, along with some continuity regarding the premiere’s Y2K bunker, to suggest a Victorious Premise (funny from the idea alone) in which a judge rules that the foursome is legally classified as a gang, and are therefore forced to separate and avoid seeing one another. Obviously this is an episodic predicament, but the plot’s play towards the series’ strongest emotional bonds — prior to the Drew/Kate coupling that forever alters (and weakens) their chemistry — is a thesis-related font of comedic drama, worthy of our investment and capable of pulling big laughs, especially with a teleplay credited to O’Keefe. This is one of the last shows that feels like classic, old school Drew Carey — raucous and uncomplicated.

02) Episode 105: “Drew’s Reunion” (Aired: 10/13/99)

The group goes to its high school reunion, where Kate learns about Drew’s crush on her.

Written by Brian Scully | Directed by Gerry Cohen

Although this installment never reaches the heights its amusing premise seems to promise, it’s an instrumental outing that pushes forward the now-inevitable Drew/Kate pairing, and thus changes the course of the series. Fortunately, the script manages to ensure that the year’s anticipated number of laughs are delivered — notwithstanding the gimmicky inclusion of Bo Derek, who doesn’t add much (aside from a capper to the Oswald subplot, which we’ve seen play elsewhere… and better) — and it’s generally an amusing show. However, I really wanted to discuss it here because I think it’s telling that the show tries the same device Friends used to ultimately pair its central couple (Ross/Rachel): going back into the past and using the characters’ shared history as the selling point. As discussed above, I don’t think Drew Carey is nearly as successful at motivating these emotional developments, but it’s a wise tactic.

03) Episode 106: “Drew’s Physical” (Aired: 10/20/99)

Drew has Lewis take a company physical for him.

Written by Linda Teverbaugh and Mike Teverbaugh | Directed by Tommy Thompson

What’s most appealing about this offering is its ability to balance Drew’s life in the office with his life at home, as he convinces Lewis to take the company physical for him… which goes about as well as you’d expect: Drew is called physically fine, but mentally not-so-much. Again, it’s a Victorious Premise, but the text is idea-elevating, for the episode’s ultimate goal is to contrive a reason for Kate to delay revealing her feelings to Drew (until November Sweeps, of course), and it’s motivated through both well-executed humor — the sequence in the first act where Kate confesses to Lewis how she feels about Drew is hilarious — and the plot, when the doc (Lawrence Pressman) evaluates Drew and tells him to stay away from relationships until he learns to love himself. Also, Debbie Lee Carrington makes one of her four appearances as Doreen, the Mini Mimi. (She’s another example of Five trying to reignite the workplace.)

04) Episode 108: “Red, White, And Drew” (Aired: 11/03/99)

Drew turns his house into a polling precinct hoping to get a vote passed against a pothole.

Written by Mitch Hunter and Jana Hunter | Directed by Gerry Cohen

Truthfully, I thought about replacing this episode with either of the two close-to-the-list Honorable Mentions below, which are essentially more gimmicky-yet-notable outings. However, this good old-fashioned self-contained cut-above-the-rest entry is hard to ignore. Its story is situated in the personal realm, as Drew turns to local government to combat a dreaded pothole and then volunteers his house as a replacement voting precinct. The big comedic centerpiece occurs after Lewis, Oswald, and Mrs. Hopkins (Pat Crawford Brown, who’s hysterical) turn the place into a booze-filled party and then accidentally set the ballot box on fire, forcing Drew and his guests to recreate their votes while Lewis and Oswald distract the election official outside. It’s a farce, but it’s fun, and showcases the core four friend group well. Underrated.

05) Episode 114: “Drew And The Racial Tension Play” (Aired: 01/05/00)

Drew comes under fire when a board member makes racist comments during a speech.

Written by Dan O’Keefe | Directed by Sam Simon

Drew Carey enters the calendar year 2000 with a major change at the office, delivered near the end of this entry when the aforementioned Mr. Soulard (Mark Curry) supplants Nan Martin’s Mrs. Louder as the most visible oppositional force in the Winfred-Louder boardroom. As we noted above, this change doesn’t necessarily beget all the opportunities the year likely hopes, but this particular installment is fairly enjoyable, thanks to O’Keefe’s teleplay and another Victorious Premise in which Drew has to make amends after a board member he picks to speak at the company’s centennial delivers a bevy of racist remarks. Also, the subplot, in which Lewis dates Doreen, the Mini Mimi, makes for a tight, memorable home/office B-story.

06) Episode 119: “Drew Goes To Hell” (Aired: 02/23/00)

Drew and Mr. Wick strike an alliance to each get the other promoted.

Written by Holly Hester | Directed by Gerry Cohen

This straightforward workplace offering — coming during the year’s push to recommit itself to telling office stories (with only a modicum of success) — ultimately launches the temporary arc in which Drew takes Wick’s place as the store manager, a change-up that’s not only short-lived, but also unrewarding, too. (That is, the show doesn’t really get comedic story from the structural change, which is disappointing.) Nevertheless, this one is a hoot, taking great advantage of Craig Ferguson’s Mr. Wick by restoring some of his initial villainous undertones and positing him as The Devil, when he and Drew make a bargain to help each other get promotions — if Drew recommends Wick for the board, then Wick’ll recommend Drew for manager.

07) Episode 121: “The Gang Stops Drinking” (Aired: 03/22/00)

Mimi makes the foursome temporarily allergic to alcohol.

Written by Terry Mulroy | Directed by Gerry Cohen

The year of Victories In Premise continues in this outing which, I admit, doesn’t quite live up to its potential either but is still memorable enough to earn rank among the season’s finest. In the vein of the beer that ratchets up everyone’s libido (from Season Three’s “The Sex Drug”), this entry has Mimi feeding the core four a substance that makes them temporarily allergic to alcohol. It’s a fun idea, but the Oswald/Lewis scenes, where they double date with a pair of recovering addicts, are much more enjoyable than the Drew/Kate material, which attempts to yield a drunk discussion about their relationship (and the prospect of moving in together), yet doesn’t do much but continue the season’s forced prolonging of any development.

08) Episode 123: “Mr. Wick Returns” (Aired: 04/12/00)

Drew and Mr. Wick scheme to keep Mimi from becoming store manager.

Written by Aaron Spiro Skentzos | Directed by Gerry Cohen

Four episodes after Drew was promoted, he’s back to where he was before, courtesy of Wick, who hopes to get his job back and hires a cowboy to tie Drew up (literally) before an important sales day — inadvertently giving Mimi the chance to try-out for the manager position herself. That’s a great set-up for the rest of the story, in which Drew and Wick join forces (again) to bring down Mimi, leading to a hilarious climax (no pun intended) — and the reason that this excursion is a winner — in which the remote control for Mimi’s vibrating panties (that she’s wearing as part of her arc of trying to conceive a child with Steve) falls into precisely the wrong hands at (for her) the wrong time. (Shades of Marcy D’Arcy and her bank speech…)

09) Episode 126: “Drew And Kate Boink” (Aired: 05/10/00)

The time has come for Drew and Kate to consummate their relationship.

Written by Robert Borden | Directed by Gerry Cohen

Even though I maintain that the year hasn’t properly justified the Drew/Kate relationship and instead relied on the audience’s loyalty to a seemingly long-buried character want from the first season to support the investment, it’s nevertheless a relief when the show stops its unnecessary slow-walking and truly progresses it. Here, in what is narratively the year’s finale, during which Mimi and Steve’s quest to conceive yields a positive result, Drew and Kate finally “boink” — after a season in which a psychiatrist’s evaluation of Drew kept her from confessing her feelings, a stomach ache prolonged their first date, and a broken penis (yes, February Sweeps, folks) apparently took three months to heal… But, honestly, it was worth the wait, for this well-scripted offering operates with some classic Drew Carey charm, best evidenced by the “L-O-V-E” musical number — a familiar gimmick that’s been underused this year and can therefore serve as both a callback to an earlier era and an emotionally satisfying beat.

10) Episode 127: “A Very Special Drew” (Aired: 05/17/00)

The Drew Carey Show tries to win an Emmy.

Teleplay by Apryl Huntzinger | Story by Jerry Belson | Directed by Gerry Cohen

In a year that made use of tired gimmicks like live shows and “what’s wrong with this episode” episodes, this is a stunt that’s actually as fresh and original as it needs to be, as the series breaks the fourth wall and expresses its resentment at never having won any Emmys. This is the show’s tongue-in-cheek bid to be nominated, filled to the brim with pretentious, clichéd, and melodramatic storylines — like Kate’s life-threatening illness (which allows the very pregnant Christa Miller to stay in a hospital bed), Mimi’s OCD, Drew’s illiteracy, Oswald’s kleptomania, and Lewis’ emotional guardedness, which he verbalizes in spotlighted straight-to-the-audience soliloquies. It’s all a big burlesque, but in this case, it’s unique enough to survive on its own gimmickry, and the entry, co-credited to sitcom vet Jerry Belson, maximizes the concept.


Other notable episodes that merit mention include: the two closest to the above list, “Drew Live,” a semi-improv’d show that was performed live three times for Eastern, Mountain, and Pacific audiences, and capitalizes upon the spontaneous strengths of some of the cast (along with guests Brad Sherwood, Wayne Brady, and Colin Mochrie), but doesn’t have the necessary comedic meat, and “Drew’s Stomachache,” in which Drew’s stomach hurts every time he thinks about dating Kate, leading to a memorable (and very Carey) scene where Drew talks to his stomach (and there’s also the popular, but stunty, subplot where Mimi tries to get an annulment from her first husband, Eddie Money). Offerings of more Honorable Mention quality include: “Drew Tries To Kill Mimi,” which would be great if it wasn’t essentially a clip show; “Steve And Mimi Get Married,” a self-explanatory big development; “Kate Works For Drew,” which tries to bridge the personal and the professional; “Oswald’s Son,” a surprisingly heavier outing for Oswald and Lewis; and “Beer Ball,” which pits the Carey brothers against each other in softball (and would be fun — if Steve was better defined).


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

“Drew And The Gang Law”



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

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

  1. i like kate with drew but now how it was handled . this is the last really good season imo . some great eps here.

Comments are closed.