The Ten Best WILL & GRACE Episodes of Season Five

Welcome to a new Sitcom Tuesday! This week, we’re continuing our coverage on the best of Will & Grace (1998-2006, NBC), which is available on DVD and streaming!

Will & Grace stars ERIC MCCORMACK as Will Truman, DEBRA MESSING as Grace Adler, SEAN HAYES as Jack McFarland, and MEGAN MULLALLY as Karen Walker.

On paper, Season Five seems like a return to form. After a disappointing fourth year that halted growth for the main characters and devolved into a cliffhanger-driven mess with Will and Grace trying to conceive a child (which was a mistake — see last week’s commentary), Five handily eradicates this unfortunate plot and moves forward with arcs that offer positive evolution — not only for Will, who plays Pygmalion to a young gay man in a four-part storyline with Jack that’s brief and not spectacular, but a welcome and more thesis-related narrative than his usual material in this era, but also for both Karen, who becomes single after Stan takes up with a mistress (Minnie Driver), and Grace, whose spontaneous marriage best represents all of this apparent forward momentum. Furthermore, despite the reduced involvement of creators Kohan and Mutchnick, who left for Good Morning, Miami and would be credited with no more Will & Grace scripts until the series finale, Season Five is a palpably funnier year than its predecessor, with an increased emphasis on big laughs that, as usual, come packaged to MSTV gimmicks that have started to define the show — like casting stunts (this year’s roster includes Kevin Bacon, Gene Wilder, Katie Couric, Elton John, Demi Moore, Madonna, and Macaulay Culkin, among others) — but they’re no less bothersome than the previous year’s. That is, Five’s Sweeps-based shenanigans are no less a distraction from the characters than the previous few years’ have been, meaning there’s no additional disappointment inspired by the use of this otherwise unideal element of the series’ identity… Also, adding to the year’s positive reputation is the fact that its leading lady, Debra Messing, finally won an Emmy for her work here, elevating Will & Grace into an elite club of sitcoms — next to only All In The Family and The Golden Girls — where every lead performer was so honored by the Academy. So, Season Five is a year that should make the series, and its fans, proud, right? Well… while all the above is true — particularly that the MSTV aspects of the series’ identity are no more condemnable this year than in the previous, and that, as a whole, Five looks to push the characters forward more than Four — the devil is in the details. And by devil, I mean Leo (Harry Connick Jr.).

Yes, the very thing that offers Grace the forward movement that we celebrate because it implies a concern for character, is also what belies the year’s value, for Leo is, unlike Nathan (Grace’s most recent beau), an undefined knight in shining armor who provides nothing by way of character drama or comedy and might as well be a cardboard cutout, given how little he contributes to this story-led arc. He’s introduced as Grace’s ideal partner as a means of getting the series out of its baby mess, and okay, we can at least thank him for helping with that. But as the year progresses and Leo continues to elude definition, he becomes a liability, especially when the show forces Grace into a November Sweeps wedding that hopes to bring her full circle from the pilot (where she ran out on her fiancé), but instead leaves us cold, for if we don’t know enough about Leo to root for the pairing, then the show’s attempt at moving her forward is not a success — we don’t buy it. It’s the opposite of what happened with Nathan, whose relationship with Grace ended without motivation; here, Leo’s marriage to Grace starts without it, and is entirely predicated on this weakness. When the year takes him out of the picture — sending him off in Doctors Without Borders — it’s a situational triumph, for stories are now free of a character-starved problem, but a foundational failure, for when scripts aren’t forced to develop a personality — and flaws — for Leo, he therefore remains perennially underdrawn, with the pair’s only drama existing as a situational contrivance: distance. This will remain an issue throughout Six too, trapping Grace (and the show) within an arc that, while intending to signal a rededication to the series’ regard for character, actually enables the real issue: neither Will nor Grace get much motivated emotional growth explored within episodic story. Instead, there are weekly distractions, many of them funny — see the list below — and if that’s enough for you, then this is a good year. If not, well, I’m afraid the rest of this ride is going to be bumpy… That said, I have picked ten episodes that I think exemplify this year’s finest.


01) Episode 100: “Bacon And Eggs” (Aired: 10/03/02)

Jack becomes an assistant to the star he’s been stalking: Kevin Bacon.

Written by Alex Herschlag | Directed by James Burrows

When I wrote above that the use of guest stars was no more disappointing this year than in the previous, I want to reiterate that I’m making this statement in relation to Season Four, whose star-driven shows have the exact same problems as those here do: they put too much stock in the gimmick, and decentralize the regular characters the series is most primed to serve. To wit, I no more enjoy the overrated “Bacon And Eggs,” built around Kevin Bacon, than I do the prior year’s “Fagel Attraction,” with Michael Douglas, and I maintain that, however well these installments represent the MSTV part of the show’s identity, it’s not the most ideal use of Will & Grace‘s time. And yet, unlike other guest star shows from this era — like, say, the Madonna entry cited below as an Honorable Mention — this popular episode benefits from having Bacon play himself, for even though he does steal too much focus away from the regulars, his inclusion is inspired by Jack’s obsession, meaning that, to a certain degree, the gimmick is legitimized by a character trait. Additionally, the subplot that resolves Karen’s near-affair with Rip Torn (not playing himself) offers worthwhile laughs of its own that boost the half-hour’s appeal.

02) Episode 101: “The Kid Stays Out Of The Picture” (Aired: 10/10/02)

Grace wants to postpone the next insemination because of Leo.

Written by Jhoni Marchinko | Directed by James Burrows

As the first half of the two-parter that extricates the series from the dreadful “Will and Grace plan to have a baby together” arc, “The Kid Stays Out Of The Picture” is a functional show with story concerns driving its very existence. And while we’re glad for what it does — ending a terrible plot that would have done the opposite of moving the characters forward in a positive direction — it’s hard to ignore that it has an agenda other than simple character exploration. Fortunately, though, in order to wrest the pair from this “hand of writer” notion, the show forces them to confront some painfully honest truths about their relationship, specifically the thesis-ordained central conflict: their codependent friendship is fueled by their mutual inability to find the happiness they seek, and could perhaps be the cause of it. The final confrontation between Will and Grace pulls no punches and is likely the most explicit the series EVER lets the characters be about the drama that underscores their bond. Given how poor the show has been at addressing its thesis in episodic story, this self-awareness is primo, and unlike the next outing, it can lean into this conflict without having to resort to slapstick distractions that mask the contrived need for reconciliation, which stretches emotional credulity.

03) Episode 103: “It’s The Gay Pumpkin, Charlie Brown” (Aired: 10/31/02)

Grace tries to bond with Leo in the country, while Karen catches Stan cheating.

Written by Gary Janetti | Directed by James Burrows

Admittedly, I struggle with this one because of its on-location hit-and-miss A-story that tries a little too hard to make us buy into the romance between Grace and Leo, never mind how little definition he’s still receiving. Oh, sure, the entry hopes to derive conflict by depicting him as outdoorsy while Grace, to her comedic chagrin, is unable to even fake a reciprocal interest, but those accompanying laughs come situationally (Grace vs. the bike, Grace vs. the rain, etc.), and would generally work regardless of the Leo character — as I said in reference to this whole storyline, he might as well be a cardboard cutout. However, the rest of the teleplay is rich with both hilarity and dramatic meat, as Will is paired with a “pocket gay” in a laugh-laden subplot, and Jack helps Karen deal with a surprising revelation: Stan, just out of prison, is cheating on her, thus launching a whole new arc for her, and one that — thankfully — opens Karen up to new story that makes her a more vulnerable character (but without forsaking any of the big hahas she provides). So, this is one of those rare shows that compensates for the series’ present macro problems — evidenced in the A-story — by good micro decisions in the periphery.

04) Episode 104: “Boardroom And A Parked Place” (Aired: 11/07/02)

Karen begins sleeping in her limo, while Will gets a new boss.

Written by Gail Lerner | Directed by James Burrows

Gene Wilder won an Emmy for his work in this Sweeps installment, where he plays Will’s new boss, a recent patient at a mental institution. In fact, Wilder’s work was so well-received that the series brought him back for another show later this year (the middling “Sex, Losers, And Videotape” — don’t look for it below). Frankly though, I’m sorry to say that a regard for both of his entries eludes me; aside from the general problem that this series has with guest stars — allowing their inclusions to crowd out worthwhile character concerns that could otherwise justify the stunt — I think the depiction of mentally unstable characters on sitcoms tends to be both hacky and immune to emotional investment, for “crazy” is a little too nebulous a motivator of comedically flawed behavior, and to me, indicates lazy character writing. Accordingly, while I like Wilder, if not for the more favorable B-story — which works because of the inverse of character-based expectations, as Karen is now homeless and forced to reside in her limo after leaving the philandering Stan — I probably would have relegated it to the Honorable Mentions, alongside the similarly tacky and character-starved Madonna outing. But, like “Bacon And Eggs,” this is also a better-written show than a few of the year’s other guest-star-led efforts.

05) Episode 106: “Marry Me A Little (I)” (Aired: 11/21/02)

Grace and Leo impulsively decide to get married.

Written by Jeff Greenstein & Bill Wrubel | Directed by James Burrows

Originally broadcast in an hour-long block and promoted as the series’ official one-hundredth telecast (not counting all the ones that were split into two for syndication), this two-parter claims the biggest development of the season, as Grace marries Leo, suggesting that her character is finally on the road to a happy ending. Now, we’ve discussed above why this isn’t exactly the case, and watching “Marry Me A Little” with that mindset naturally makes it a disappointment, for not only are there many of the Sweeps-y things we hate about this series — the on-location scenes, the shameless guest cameos (Katie Couric, for instance), the large narrative-led storytelling — there’s also the unavoidably porous foundation for this relationship. That is, we don’t know who Leo is and we therefore don’t believe he and Grace should be together. So, this hangs over the show like a dark cloud, but if one were to take what the series says at face value, then appreciating this episode would be easier, for it really does make it seem like Grace is getting precisely what she wants, and unlike Part II, which is totally redundant but offers fewer laughs as it has more sentimental Will/Grace moments to cover, there’s joy here — earned or unearned, it doesn’t matter — that makes this excursion notable, if not great.

06) Episode 113: “Homojo” (Aired: 02/06/03)

Jack befriends Stan’s new mistress as Will and Grace attempt to reconnect.

Written by Bill Wrubel | Directed by James Burrows

The only true MVE runner-up this season, “Homojo” is the most flattering example of Will & Grace during this period in its life. On one side, there’s a subplot with a big-name guest star — Minnie Driver — who gets huge laughs interacting with the show’s goofiest twosome, Jack and Karen, while the eponymous leads get a somewhat sincere A-story that attempts to address how their dynamic has changed in light of the Leo mishegoss. But in both cases, there’s a lot of smart decision-making occurring — in the Will/Grace A-story, the characters are allowed to be self-conscious about the shift in their relationship, and how it’s not been as satisfying as of late (not because Grace is growing up, but because she has moved out and is trapped in a relationship with someone for whom we don’t particularly care). And the offering turns back to the ol’ game night routine, established in the pilot as a way to show us just what a tight twosome they are, with Rob/Ellen and now Joe/Larry. It’s reliable, effective, and indicates an awareness of the series’ roots. At the same time, the use of Minnie Driver is more than just a Kevin Bacon/Madonna stunt, as she’s cast as Stan’s new whore, thereby rendering her a worthy foe for Karen and a comedically (and dramatically) ripe presence to include in episodic story as the series continues to explore this fresh arc. It’s a lot of fun. Again, it’s an MVE contender.

07) Episode 115: “Fagmalion Part Three: Bye Bye Beardy” (Aired: 02/20/03)

Will realizes he has feelings for Barry, while Karen feuds with Beverly Leslie.

Written by Alex Herschlag | Directed by James Burrows

Honestly, I have some mixed feelings about the four-part Barry (Dan Futterman) arc, which finds Jack and Will doing the Pygmalion routine for a schlubby guy who’s just come out of the closet. In these four episodes, all of the Barry stories tend to work, but they’re pretty much consistently predictable and, given that they’re supposed to provide Will with a little more substantive material (romantically), I think they inevitably end up being far less consequential than they could have, and should have, been. On the other hand, they nevertheless do constitute some of Will’s best stuff during this three-year gap where he has no serious love interest, and for that reason, they’re certainly recommendable. Now, I’ve selected the third part to represent the entire tetralogy because unlike the expositional premiere, the comedically-geared follow-up, and the “all for naught” conclusion, this one provides the most hope, finally pivoting the story so that Will’s emotional investment in Barry is the focus of the action, enabling the possibility of forward momentum for his character. Also, the teleplay is the smartest of the “Fagmalion” four, benefited by a construction that puts the characters all together at the same time and place, and with some choice material between Karen and her ever-ready rival, Beverly Leslie. In essence then, this is the most enjoyable show in the whole Barry arc.

08) Episode 120: “May Divorce Be With You” (Aired: 05/01/03)

Will has to represent Stan in the latter’s divorce case against Karen.

Written by Sally Bradford | Directed by James Burrows

It’s May Sweeps and following the much-discussed Madonna showcase the week prior, this outing’s guest star du jour is former child star Macaulay Culkin, playing Karen’s lawyer, a juvenile whose ostentatious naïveté is proven to be just a calculated performance intended to crush the unsuspecting Will, who’s forced to go against Karen and represent Stan in the couple’s divorce proceedings. The gimmick of Culkin’s presence is exacerbated by the fact that he’s exploiting his image to play against type, but it’s dramatically legitimized by both the teleplay’s success at achieving its attempted big laughs and because the premise is a natural outgrowth of Karen’s broader arc, which has continued to provide good narrative fodder for her character. It’s ultimately one of the best uses of a named guest star this year. Additionally, there’s fun stuff in the subplot, as Grace gets a job decorating for Jack’s new boyfriend (played by The New Adventures Of Old Christine’s Clark Gregg), who then dumps Jack, forcing Grace to sneak behind her friend’s back as she schemes to finish the job. Again, there are many laughs in this memorable yarn, which, like all the May Sweeps shows, were initially supersized.

09) Episode 121: “23” (Aired: 05/08/03)

Stan dies suddenly and Karen worries about what’s in his will.

Written by Adam Barr, Jeff Greenstein, Gary Janetti, Sally Bradford, & Alex Herschlag | Directed by James Burrows

My choice for the season’s Most Valuable Episode (MVE), the simply titled “23” earns this honor because it’s, quite frankly, the funniest show of the season, and since Will & Grace is becoming less concerned with the sincere dramatic use of its characters and is instead preferring to be judged by the success of its episodic ability to pack in high-octane laughs, this then feels like the most victorious possible offering based on these new emerging standards. That’s not a backhanded compliment though, for “23” is more than just a laugh riot — it’s also the culmination of Karen’s seasonal arc, as her divorce from Stan has been called off following his death, which forces her to once again confront his new mistress Lorraine, played by Minnie Driver, and brings up the delicate matter of what he left to them in his recently revised will. It’s played broadly — as per the series’ norm — but it’s filled with terrific moments of emotional honesty, like when Karen is revealed to be the love of Stan’s life, and outrageous comedy, like when Rosario thinks she’s won her freedom, only to have her dreams crushed. Also, the segment — supersized in its original showing (but not on DVD) — benefits from the majority of the action taking place at the funeral, which puts all the characters together (including Leo, whose next departure is set up here) and allows them to bounce off each other as comedic forces of nature. It’s a joke-a-minute, but unlike so many of the other Sweeps shows from this era (with their gaudy casting stunts), it’s not trying as hard: it’s just using what’s been established. So, believe me when I say, this is one of the funniest installments of the entire run and a very favorable portrayal of the series’ strengths in this complicated season.

10) Episode 122: “24” (Aired: 05/15/03)

The group joins Karen as she spreads Stan’s ashes out in the Caribbean.

Written by Gail Lerner, Kari Lizer, Jhoni Marchinko, Tracy Poust, Jon Kinnally, & Bill Wrubel | Directed by James Burrows

Season Five’s finale continues where the penultimate entry paused, and while it’s not as enjoyable as the previous — especially if you see it in its original (not on DVD) supersized form, which includes a lot of unnecessary fat, like a cameo from Debbie Harry — it primarily works because it’s an extension of the comedic and dramatic opportunities introduced in its predecessor. In addition to more of the delicious Karen/Lorraine feud, which follows the group as they yacht around the Caribbean while Karen prepares to dump Stan’s ashes, it builds to a Grace/Leo cliffhanger as the latter decides not to accompany her man as he once again (and very conveniently) has to dash across the world to provide his medical expertise, even though she’s jealous of his obnoxiously attractive coworker (played by Nicollette Sheridan). It’s easy comedy and involves at least one character about whom we care way too little, but it hits all the right notes. For the most part, the same can be said for the Will/Jack story, which started from Stan’s will (when he encouraged the two to get together already) and plays to the long-held rom-com belief that the show’s two gay leads would eventually have a love story of their own. It’s fine character comedy, until the stunty final moments where they end up in bed together. But, hey, that’s going to be Season Six’s problem, right? Stay tuned…


Other episodes that merit mention include: “Women And Children First,” which was the closest to the above list due to a Victory In Premise with guest star Demi Moore as Jack’s old babysitter and a decent bonding story for Karen/Grace, and all the other parts of the Barry arc, especially “Fagmalion Part Four: The Guy Who Loved Me,” which ends everything without enough emotional relevance for Will, but within a teleplay that boasts a fun Karen subplot. Of more Honorable Mention quality are “Humongous Growth,” which toils to repair Will/Grace’s friendship and must resort to slapstick gimmickry, “The Needle And The Omelet’s Done,” which introduces the idea of Jack’s acting method, “The Honeymoon’s Over,” an idea-driven show with an Elton John cameo, and “All About Christmas Eve,” which I like for the delectable ensemble interplay. Oh, and I have to mention “Dolls And Dolls” with Madonna; it offers nothing of character value, but it’s memorable.


*** The MVE Award for the Best Episode from Season Five of Will & Grace goes to…




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

8 thoughts on “The Ten Best WILL & GRACE Episodes of Season Five

  1. Leo’s one of the worst examples of a love interest who’s not given any definition. All of the NBC shows from this era suffer from this problem at one time or another.

    Also, good MVE pick. “23” is one of the funniest episodes of the entire series.

    • Hi, Nat! Thanks for reading and commenting.

      Yes, FRIENDS, in particular, had quite a few love interests with the same problem!

  2. Love Gene Wilder but his episodes don’t do him justice. That being said I’m glad you included his first episode because its such a joy to see him and I also really like the Karen subplot too.

    I HATE HATE HATE the Madonna episode. She’s got terrible timing and it makes no sense. Do you think they would have been better off having her play herself, like Cher or Kevin Bacon?

    • Hi, Elaine! Thanks for reading and commenting.

      I think having Madonna play herself would have possibly allowed for a story where the regular characters were more central to the action, so, yes, that could have made for a better episode!

    • Hi, Eboni! Thanks for reading and commenting.

      Yes, they’re a lot of fun together — and “23” is their best showing!

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