The Ten Best WILL & GRACE Episodes of Season Four

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.

The fourth season of Will & Grace is the point in the series’ run where the wheels of the figurative bus begin to come off, and it’s something of a surprise, for although the negative MSTV-inspired trends we observed last week are accelerated here, the year itself starts strong. In addition to continuing Grace’s relationship with Nathan (Woody Harrelson), her most nuanced and defined love interest of the entire series (Leo will prove to be more of a device than a character), Four starts by promising continued emotional evolution for all the regulars, like Karen, who has to cope with the sudden arrest of her beloved Stan, and Jack, who tries to be a dad to his newfound teenage son, Elliot (a congenial recurring presence who tends not to make for classic offerings, but nevertheless helps dimensionalize Jack). But then something awful happens: the season’s signature arc — the Grace/Nathan relationship — comes to a crashing halt during November Sweeps… without a legitimately character-motivated catalyst. That is, this relationship — an engine of growth for Grace — is ended for a reason that has nothing to do with her own flaws (or her bond with Will), and it’s an insult to both the audience and the character, for whether his quick departure is merely a function of Harrelson’s contract, or the need for a plot shake-up, or even the desire to prolong Grace from getting her happy ending (as all long-running MSTV hits have to do in order to string out narrative developments), the result is the same: forward progression is rescinded, or at the very least, halted, without justification. And what’s more, the demise of this relationship seems to coincide with problems for all the others too, as the character-rich stories seen at the year’s open quickly give way to more idea-driven fare — narrative gimmicks, gaudy guest stars, and plots that generally have nothing to do with the central dramatic thesis and/or Will and Grace’s search for love. I wish I could explain the cause — some have attributed this to the dwindling involvement of creators Kohan and Mutchnick, who were developing Good Morning, Miami at the time (making this the last year where they’re regularly credited for Will & Grace scripts), but that’s just conjecture.

The only thing that’s clear is that we can no longer rely on episodic story to either routinely reinforce the core conflict between Will and Grace, or more to the point, prioritize character evolution above sexier, shinier interests — like Sweeps spectacles or the broadening comic sensibility that’s been emboldened by raging MSTV-itis, specifically casting gimmicks, which increase exponentially here. While a few guest stars get something resembling dramatic sincerity — see: Blythe Danner as Will’s mom — many of the year’s cameos and high-profile roles are nothing but distractions. There are a lot, but the grandest and most narratively ostentatious appearances come from Rosie O’Donnell, Suzanne Pleshette, Michael Douglas, Glenn Close, Cher (again), and, most famously, Matt Damon. Now, not all of their entries are bad — they’re fundamentally notable, and sometimes hilarious — but they serve as a constant reminder that in the middle of Season Four, character stories stop and weekly dog and pony shows take over… at least until May Sweeps, when the year has to build to a cliffhanger and thus decides that Will and Grace, heretofore stagnated for the better part of a season, should consider having a child together. It’s a dreadful idea — not only because, like the Nathan breakup, it seems to arise from an external force other than the characters, but also because it symbolizes defeat. If their shared goal is to find romantic love, then giving up on the prospect of raising a child with their most ideal partners because they instead have the option of falling back on each other is the ultimate example of the relationship being detrimental to their individual happiness. And though we root for the two to get their happy endings and still remain in each other’s lives — as their use in the first three seasons indicated was possible — we certainly don’t root for a baby, which will make it harder to fix their unhealthy dynamic and finally get what they both want. Therefore, Four ends with story interests that promise nothing good for the characters… Fortunately, Five will get the pair out of this pickle, but then, well, it’s got some troublesome stuff of its own; stay tuned… In the meantime, I have picked ten episodes that I think exemplify this year’s strongest.


01) Episode 72: “The Third Wheel Gets The Grace” (Aired: 09/27/01)

Nathan tries to be like Will in his relationship with Grace.

Written by David Kohan & Max Mutchnick | Directed by James Burrows

Season Four opens with promised growth for the main characters via a thesis-inspired story where Will returns from his vacation and makes Nathan feel like the third wheel in his relationship with Grace, thereby illustrating the central conflict: Will and Grace’s difficulty to maintain a serious romance and get the love they seek because of their unhealthy reliance on each other. This idea manifests itself in a fun story where Nathan takes Will’s place shopping with Grace, only to realize that she’s such a handful that he’s grateful for the part Will plays in her life. Meanwhile, shopping is used as the center for the other stories too, as Karen gets an amiable yarn with Rosario that supports the sincerity of their dynamic, and Jack attempts to bond with his new son, Elliot, introduced in last year’s finale, by picking out clothes with him — a supreme way to exploit the comic discrepancy of Jack’s paternalism and his ideas of what boys typically like. It all jells wonderfully, within a funny, sharp, and narratively efficient script — credited to the co-creators — that (falsely) predicts great things for Four…

02) Episode 74: “Crouching Father, Hidden Husband” (Aired: 10/11/01)

Jack and Grace go to his son’s school dance while Karen gets bad news.

Written by Adam Barr | Directed by James Burrows

Truthfully, this is a well-liked episode that I would have been perfectly fine including among the Honorable Mentions… if there was a better replacement than this — an above-baseline outing that benefits simply by being in the early part of the year, where forward progression for all the characters looks likely, not just for Grace in her relationship with Nathan (even though that’s the most important ambassador of this trend). The A-Story once again involves Jack attempting to be a father for Elliot, which is a natural struggle, and while I maintain what I expressed above — Elliot shows aren’t great (he’s a functional distraction away from thesis concerns) — he’s also a worthy foil for Jack and he forces an expansion of that character. And so, despite a gaudy narrative centerpiece such as the one here, there’s intrinsic value in most Jack/Elliot plots… Actually though, the better premise is the seemingly less significant one, in which Karen keeps crying wolf to Will only to really need him when the FBI shows up inquiring about Stan… who’s been arrested. It’s the start of a new arc for her character, and it’ll bring some decent stuff, right now providing choice laughs that elevate this segment above its competition.

03) Episode 75: “Prison Blues” (Aired: 10/18/01)

Will goes to acting class with Jack while Grace enjoys living with Karen.

Written by Alex Herschlag | Directed by James Burrows

Although opening with a scene where the characters go to visit Stan in prison, making us think that the entire action will be set there, this aftermath to the previous entry’s narrative bombshell merely uses that bit as the catalyst for two separate stories, both of which are enjoyable. The less notable one has Grace staying with Karen to keep her company after the visit, only to grow accustomed to the pampering and refuse to leave. It’s nothing but a fun idea and a chance to explore the two ladies’ interplay outside of their usual office setting. More worth highlighting is the premise of Will trying to become a natural on camera and thus deciding to join Jack at his acting class, where we meet a new recurring character, the menacing Zandra, played by the brilliantly funny Eileen Brennan. Her unique comic energy is a boon to all of her appearances over the next few years, but as is customary, her debut offers us the most distilled idea of her purpose: deflating Jack, whose acting chops leave a lot to be desired. But there’s more than just comedy on this story’s mind; it also has some sincere drama with Will, who apologizes to himself in an acting exercise and seems to have his own catharsis.

04) Episode 76: “Loose Lips Sink Relationships” (Aired: 10/25/01)

Jack tries to arrange a date for his female boss… with Will.

Written by Kari Lizer | Directed by James Burrows

Parker Posey makes her first of two appearances in this outing as Jack’s prickly boss at the department store. There’s something of a classic situation comedy premise here, as Jack agrees to set his boss up with Will, whom she finds attractive, in exchange for time off to go to an acting class showcase. Of course, this is unbeknownst to Will, who otherwise wouldn’t agree, because, well, he obviously won’t ever have any sexual interest in her. So, a familiar comedic idea is made more original by these characters… Meanwhile, the other story has Nathan and Grace comparing their total number of sex partners, and then discovering that just because Grace has had more than Nathan, she’s actually done “it” far fewer times. While this is a fine premise — an attempt to use the differences between the two for comedic drama (which is what we want) — the real hahas and the crux of the episodic conflict come courtesy of Karen, who gives the pair perfectly opposed advice about what they should do to cope with feeling inferior about their stats. It’s a lot of fun and Karen’s scenes, in particular, shine in what is already a buoyant, easy-to-like offering from a temporary high point in the show’s run.

05) Episode 78: “Bed, Bath, And Beyond” (Aired: 11/08/01)

The group tries to help Grace get over her grief about Nathan.

Written by Jhoni Marchinko | Directed by James Burrows

My choice for the season’s Most Valuable Episode (MVE), “Bed, Bath, And Beyond” is one of those half-hours that serves a narrative purpose: providing emotional continuity from the previous, in which Nathan broke up with Grace… for a reason that had nothing to do with the troublesome Will/Grace relationship or even Grace’s own flaws, therefore rendering the occurrence convenient and not character-driven. (Never mind that his explanation was so vague as to be insulting.) Now, we briefly discussed above why this development is a problem — it retracts forward momentum for Grace without cause — but it doesn’t really become devastating until the rest of the season unfolds and we realize that ALL growth after this fades from the year’s sights entirely, and not just for Grace, as the seemingly arc-sparked stories portending maturation for the others are also soon replaced by trivial idea-led exhibitions, many with some kind of gimmick. This installment becomes even more special in light of this hindsight awareness then, for it’s one of the last times that Four — even after what just happened with Grace/Nathan — still has something resembling hope for the characters, as evidenced by this simple and tightly plotted ensemble show with only the four regulars and Rosario. It’s loaded with character moments and is concerned with exploring how a group of friends, and mainly Will/Grace, help each other out after an upsetting setback. No bells, no whistles, no Cher; this is people interacting and commiserating over the difficult times they’ve faced. If only the rest of the year was this interested in the characters and their journeys…

06) Episode 80: “Moveable Feast (I)” (Aired: 11/22/01)

The foursome decides to pop in briefly on each of their families for Thanksgiving.

Written by Kari Lizer | Directed by James Burrows

Okay, while it’s true that quality declines considerably after “Bed, Bath, And Beyond,” the year’s two-part Thanksgiving excursion — initially broadcast in a special one-hour block — also happens to be an enjoyable character showcase, even with both the inherent structural gimmick that typifies the rest of the year’s idea-based fascination and the bevy of guest stars that threatens to distract the series from its key interests: the regulars. But said structural gimmick — the foursome deciding to pop in for an hour on each of their relatives for Thanksgiving before sitting down at a meal together — is built to prize quick character combustions, which means that the leads and their relationships are pushed to the fore. That is, in a scene at Grace’s house, for instance, which not only includes Debbie Reynolds but also Lainie Kazan and Kenneth Mars, the focus still remains on the fraught dynamic between Grace and her mom, who rejoices to learn that she was right about Nathan being the wrong guy for Grace. Likewise, the entry gets to address some of the year’s specific concerns — like Stan being jailed and the existence of Elliot — in Karen and Jack’s respective centerpieces, the latter of which includes Beau Bridges as the father who raised Jack. There are some big laughs in every set piece — supported by the ensemble’s inclusion —  and some powerful dramatic character beats, too. It’s great.

07) Episode 81: “Moveable Feast (II)” (Aired: 11/22/01)

The foursome goes back to get closure from each of their families.

Written by Kari Lizer | Directed by James Burrows

Part II is the extension of the former, and in syndication, it contends with only the Will centerpiece, where we go to his house and meet his mother — Blythe Danner portraying the WASP-iest WASP to ever WASP — along with his other brother (not the one Grace slept with in Season One), played by Jon Tenney. (Incidentally, Helen Slater also appears here as the brother’s jealous wife.) Truthfully, I don’t find this sequence as satisfying as either the Jack or Grace ones (and I also think there are better Truman family shows to come), but its maintained regard for character-rooted drama mitigates both the stunty structure and starry casting, and it continues to offer big laughs, like when Karen considers having an affair (per Stan’s request) with the plumber, played by Nick Offerman… Then, the outing caps off with a speed round, where each regular goes back to his/her own family and gains closure — briefly — for the events that transpired in the preceding encounters, allowing for resolution to come within a finite period of time, but not feel forced, as the design, again, demands quick combustions and justifies this both structurally and by the percolating nature of the conflicts.

08) Episode 87: “A Chorus Lie” (Aired: 02/07/02)

Jack tries to prove that his rival is straight.

Written by Tracy Poust & Jon Kinnally | Directed by James Burrows

Probably the most famous episode on this list and the one that, judging by comic popularity, you’d most expect to be singled out as the season’s most notable, “A Chorus Lie” is one of those unabashed Sweeps shows that springs to mind when I think of Will & Grace and its relationship with these brazen MSTV stunts. Naturally, I’m not talking about the reappearance of Leslie Jordan as Beverly Leslie — making his first return since being introduced last season as a replacement for Joan Collins — in an affable Will/Karen subplot that’s comedic on its own and would probably be recognized here anyway. No, I’m talking of Matt Damon — movie star Matt Damon — participating in one of the grandest Victories In Premise this series ever created: Jack trying to “in” a straight guy masquerading as gay to audition and appear in the Gay Men’s Chorus that Jack has long hoped to join. Despite how loud and not-so-character-rooted its conception, and how distracting it is to have a movie star in the guest role, it’s nevertheless a delicious idea — one that only Will & Grace could do, given its assortment of characters and the kind of comedic stories it’s allowed to tell. Accordingly, I think this deserves to be praised and remembered as a classic — it’s not as character-ripe as my MVE, but it’s a contender, reinforcing other parts of the series’ identity with mastery, and most importantly, BIG laughs.

09) Episode 90: “Cheatin’ Trouble Blues” (Aired: 03/28/02)

Will and Grace have an awkward dinner with Will’s secret-keeping parents.

Written by Alex Herschlag | Directed by James Burrows

As with “Crouching Father, Hidden Husband,” I confess that this is one of those entries that I wouldn’t put on this list if I thought there was a better option below. Yet because Four is a season with few great/good shows and a larger variety that could be classified as middling/flawed, I wanted to pick one that acquits the characters better than the others. This half-hour pairs Jack and Karen in a comedic subplot where the performers’ easy rapport makes it difficult to tell whether the material is terrific or merely okay, but it does better with Will and Grace, who have dinner with his parents and learn, to their dismay, that not only is his father still seeing mistress Tina (introduced in last year’s “Cheaters” — an Honorable Mention from last week that’s, for the record, better than “Cheatin’ Trouble Blues” — and seen again in the below-cited “Whoa, Nelly”), but also that his mom has taken up a lover of her own. It’s not a laugh-riot, but it’s dramatically adjacent to the thesis, for the “don’t ask, don’t tell” relationship between two people sexually unsatisfied with each other is easily comparable to Will and Grace’s own strained dynamic — making it something of a thematically pertinent notion.

10) Episode 94: “Fagel Attraction” (Aired: 04/25/02)

A detective makes up false pretenses about going undercover in order to date Will.

Written by Jenji Kohan | Directed by James Burrows

Next to the Matt Damon episode, “Fagel Attraction” is the Sweeps-iest offering to make this list, for it features another movie star clowning it up in an ostentatious Victory In Premise that has Michael Douglas playing a detective who’s so afraid of rejection that he uses knowledge of Will’s stolen laptop to invite the latter to a gay bar under the pretenses of going undercover to bust an underground “gay laptop theft ring.” It’s broad, driven by its comedic premise, and puts a guest in the center of the action, instead of the regular in whom we’re the most invested. But it’s too unforgettable to ignore, and in comparison to, say, “Hocus Focus,” which shamelessly features another big movie star, it actually doesn’t ask us to make leaps with regard to the main characters — their intelligences aren’t as insulted here as they are in the aforementioned. Additionally, this one boasts a MUCH stronger subplot: the return of Molly Shannon’s Val, who, this time, addles Grace by opening up a rival design business to steal her ideas and poach her clients. It’s Val’s weakest appearance yet, but she’s still a delightful asset.


Other episodes that merit mention include: “Star-Spangled Banter,” which has a comedic Will/Grace story that’s more thematically rich than character-driven and a fun subplot where Karen bonds with Elliot (oh, and Anne Meara appears), “Whoa, Nelly,” in which Grace sets up their gay friend Larry with Will’s dad’s mistress hoping to get her to move on, and “Dyeing Is Easy, Comedy Is Hard,” which memorably guest stars Rosie O’Donnell as Elliot’s mom. Of more Honorable Mention quality, meanwhile, are “Stakin’ Care Of Business,” with several funny ideas incompatibly paired within a middling teleplay, “Jingle Balls,” which has the attitude of a hit but strives to make its stories make sense, “Hocus Focus,” the Glenn Close show that really suffers for some illogical bits (particularly in the Jack/Karen subplot), and “A Buncha White Chicks Sittin’ Around Talkin’,” a heavy-handed self-indulgent show that aims to zero in on the characters but operates with few laughs and one sole goal: getting Will and Grace both on board with the idea of having a child together.


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

“Bed, Bath, And Beyond”



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

11 thoughts on “The Ten Best WILL & GRACE Episodes of Season Four

  1. Yeah this is the first year that’s kinda a disappointment. But I also like Nathan a lot and think the episodes at the beginning of the year are strong. It’s the last half that’s not good.

    I’m also REALLY happy you included “Cheatin’ Trouble Blues”. It’s a mature episode that only a series like this could do… broad as it may be getting. (I share your disdain for the Glenn Close episode. Woof!)

  2. The baby storyline is something I try to block out when I think of the series. LOL

    But there are some good eps here. Your MVE is one of my all-time favorites. Perfect proof why all four of this great cast won Emmys for their work.

    • Hi, Ian! Thanks for reading and commenting.

      Yes, they work so well together — this week’s MVE is a testament to their chemistry!

  3. This is the first year where I think they start giving Megan more to do in terms of drama. And I think she excels! Her work in “Crouching Father, Hidden Husband” and “A Chorus Lie” is her standout stuff this season IMO!!

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