The Ten Best WILL & GRACE Episodes of Season Three

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.

With the start of the 2000-2001 season, Will & Grace ascended to meet its destiny, finally becoming the 9:00 anchor of NBC’s most important night of comedy: Must See TV Thursday. Although most sitcoms with the Peacock logo then reflected the tenets of MSTV philosophy — a commercialistic focus that encouraged stunts to gin up ratings: gaudy cameos, narrative gimmicks, and supersized episodes — the select few chosen to be brand ambassadors on NBC’s biggest night were under the greatest pressure to deliver. Will & Grace spent its last six years within this block of programming, and part of the reason for its success was its willingness to embrace these network-ordained principles, especially once it graduated to Thursdays. Yet, at the risk of repeating myself, being an MSTV series also came with consequences — chiefly an emphasis on matters other than the characters — and one look at Three in comparison to its predecessor is illuminating. Sure, we saw early signs of “MSTV-itis” in the series’ sophomore year (see: the self-conscious February Sweeps gay kiss episode that shouted its narrative relevance while also foisting some shameless NBC cross-promotion), but Three is the first to really embody what Will & Grace will look like as an MSTV staple. Not only does it accelerate the show’s episodic reliance on guest stars, building stories around LGBT performers like Sandra Bernhard and shoehorning in Sweeps cameos from Cher (as herself) and Ellen DeGeneres (as a nun), it also employs story-led spectacles like flashback shows, a supersized outing that originally aired in a 40-minute slot (separated into two for syndication, with about eight minutes of new footage added to the new Part II), and other assorted plots that lead with their promotable, big-laugh-seeking ideas — and not their dramatically sincere, comedically motivated character concerns. Indeed, with the introduction of these regular distractions — some of which are hilarious, some of which aren’t hilarious enough — as a function of increased MSTV fidelity, it’s now starting to become easy for the series to sideline its central thesis, and this is the first year where there truly exists a tension between entries that prioritize character and entries that prioritize something else, usually stunts or story.

This tension complicates my job, for it forces me to consider when to abandon my expectations surrounding the series’ recurring use of its central thesis and instead give greater credit to offerings that support Will & Grace’s growing projection of its aggrandized comedic identity, which has certainly continued to broaden — especially between Two and Three — but can be worth celebrating… if one is ready to demand less common sense, not call character irrelevance a sin, and remain generous about the “success” of these attempted big laughs via story… Ultimately, I’m still not quite there, for I find that this tension in Three stems from the series’ maintained determination to satisfy its characters in story — they’re not fully sidelined. For instance, after a year of living apart, the twosome is back cohabitating, justifying a return to this previously rejected arrangement by their apparent individual maturations since then. That is, this is one of those rare seasons where Will and Grace both have serious romantic arcs that suggest, if not emotional evolution, then at least an attempt at some — for while Will dates Matt (Patrick Dempsey), the former’s first and only serious beau until Vince, Grace starts the year with Ben (Gregory Hines) and ends it with Nathan (Woody Harrelson), a much better developed character than her next major man, the forthcoming Leo. You see, Nathan has quirks, is comedically imperfect, and develops relationships with the other members of the ensemble, making him more viable in story. But this is no surprise — Three is much better with character than Five will be, for even though all those above developments occur shamelessly in MSTV’s distractible Sweeps (Will meets Matt in November and dumps him in February; Grace and Ben are over in November, and she and Nathan are on in May), Three’s ability to address its dramatic thesis through mostly satisfying episodic story, however arc-led, is a testament to its maintained character smarts… As a matter of fact, despite the obvious differences between this year and the prior, if there’s any season that most resembles Two, it’s Three — its laughs may be bolder, its stunts more frequent, and its stories less perfect, but it is the series’ second best showing, and the last non-disappointment, because Four is, well… stay tuned. In the meantime, I have picked ten episodes that I think exemplify this year’s strongest.


01) Episode 48: “Fear And Clothing” (Aired: 10/19/00)

After a robbery in her apartment, Grace begins staying with Will and Jack.

Written by Adam Barr | Directed by James Burrows

Following a decent season premiere that had story things to accomplish — getting Will back to the city after his convenient departure and having Grace finally choose between Josh and Ben (she chose Ben) — but otherwise earned its Honorable Mention status for some fine thesis-connected comedic material regarding Will’s jealousy of the growing bond between Jack and Grace, the year’s sophomore outing now has to set the year up for its new status quo. This means that it has to reunite Jack and Karen, whose feud over the divorce settlement with Rosario formed part of last season’s cliffhanger, and introduce the idea of Will and Grace living together once again… an unhealthy dynamic that isn’t so unhealthy this year because both characters are actually moving forward in their own individual love lives. (Hurray — growth!) So, everything in this installment is narratively opportunistic, with goals that are less about character exploration than structural decisions… and yet, the teleplay is so funny that “Fear And Clothing” ends up being a total delight — even stronger than the year’s solid debut — and a great start to this list where character may not be as front and center, but still imperative.

02) Episode 52: “Love Plus One” (Aired: 11/09/00)

Grace considers a threesome as Jack tries to flirt with a client.

Written by Richard Rosenstock | Directed by James Burrows

An obvious Sweeps excursion, this big laugh offering has two ostentatious storylines that stretch either basic common sense or the series’ institutionalized character logic, but nevertheless are both enjoyable as funny ideas from a peak-adjacent season. The A-story has Grace reuniting with an ex-boyfriend (Jeremy Piven) who wants to engage her in a threesome. Obviously, what we know of her characterization makes this a prospect that’s almost certainly not going to happen, and so even the story’s need for her to consider trying it — not to mention her showing up at the hotel — is a leap. But if we can get on board with the idea that she wants to be the kind of person who would do this, then it’s easier to enjoy the broad comedy, which is situationally driven but only works because of how out of her element Grace is… Meanwhile, the subplot introduces Patrick Dempsey as Matt, the closeted sportscaster whose turn this season will make for Will’s second most serious relationship arc of the entire series… and his only significant love interest until Vince three years later. Here, Matt’s introduced in a terribly hacky centerpiece where Jack tries to flirt with him as Will coaches through an earpiece; it’s sketch-like and asks for a strained “sitcom” sense of reality, but it’s hysterically memorable.

03) Episode 53: “Gypsies, Tramps, And Weed” (Aired: 11/16/00)

Will gets news from a psychic and Grace hires a waiter she helped get fired.

Written by Katie Palmer | Directed by James Burrows

Sweeps continues with this loud and overstuffed outing that almost seems entirely built around the special cameo from Cher that occurs in the climax, where Jack, whose obsession with Cher predates this narrative but is really hammered home here, meets the real deal but mistakes her for a drag queen imitation. It’s Lucy-esque in its silliness, but because MSTV shows tend to exist within a more palpably realistic world, the scene feels particularly over-the-top and extraneous… And yet, it’s fun — plain and simple. Also, we know his character loves Cher, so part of the excitement comes from this awareness… As for the subplots, the worst has Grace feeling guilty after having a waiter fired and deciding to hire him as an assistant… not knowing that he’s using her office as a venue for selling marijuana; it’s totally situational with surface laughs that don’t stem from her. The better premise has Will visiting a psychic (Camryn Manheim) who tells him that the man he’ll spend the rest of his life with is named Jack. Now, it’s an idea-led prospect, but it’s hilariously self-aware, addressing the belief that Will/Jack might someday couple, and it’s ripe for the series, which matches personal development to romantic success and therefore makes even the possibility of Will/Jack feel like an exploration of Will being in pursuit of his core goal. Oh, and it’s funny, too — which is the saving grace of this stunty burlesque: it truly manages to provide an abundance of hahas, and that’s why it can be recommended.

04) Episode 54: “Lows In The Mid-Eighties (I)” (Aired: 11/23/00)

The group remembers when Will and Grace were dating in college.

Written by Jeff Greenstein | Directed by James Burrows

More Sweeps fun continues with perhaps the most famous episode of the whole third season — a two-parter that originally aired in a special hour-long slot on Thanksgiving 2000 and wound up earning Eric McCormack his sole Emmy win, as it features a flashback to how his character first came out of the closet back when he was in college and dating Grace during the eponymous mid-’80s. Part I benefits from the novelty of this classic stunt (which is beloved by MSTV shows, but common on any sitcom in need of a narrative gimmick, even the best of the best) and it delights in putting all the characters in ’80s garb — Rob and Ellen, too (in an effective use of previously introduced friends to flesh out the leads’ backstory). The plot’s mostly centered on Thanksgiving at Grace’s, with Debbie Reynolds as Bobbi (and Sara Rue as Grace’s sister), and builds to Will and Grace’s first time at attempting sexual intercourse with each other. Obviously, he can’t do it, but instead of coming out right then, he inadvertently proposes marriage and that’s the note on which this half ends. It’s gaudy, but, again, it’s fun — and the script’s comedic prowess is something really remarkable, especially in the non-sequitur Karen scenes, which also occur in the mid-’80s and show us where she was at the start of her relationship with Stan. (Oh, and Martina Navratilova appears as herself.)

05) Episode 55: “Lows In The Mid-Eighties (II)” (Aired: 11/23/00)

The group remembers how Will first came out to Grace.

Written by Jeff Greenstein | Directed by James Burrows

Part II is no funnier than Part I, and if you’re watching it separately from the previous half, the novelty of its flashback device is less fresh — even when it gets cleverer, like having Karen’s story about falling for Stan pivot to how she met Rosario. But I think there’s much more character relevance in this second half, for it’s the part of the show where Will actually has to come out to Grace, thus ending their temporary ill-advised engagement. The scene itself is a little anti-climactic — it was bound to be, I’d imagine — but the script smartly realizes that because this emotional beat is historical, it needs to present some kind of new revelation to the characters in order to bring some dramatic potency into the present. That’s when it offers the idea that when Will and Grace broke up and didn’t speak for a year, he ended up sleeping with a woman — his first — to make sure that he was, in fact, gay. (This is an idea that’ll come up again, brilliantly, in an even better story later on; stay tuned…) It’s a shock to Grace, who’s hurt that there ever was another woman in Will’s life — a direct dramatic link to the thesis’ idea that they are a couple in every way but sexually, which is why romance with others is so difficult. And for these thesis concerns, the whole entry, but particularly Part II, is undoubtedly a series classic — with big laughs and important character moments. So, when making a selection for the season’s Most Valuable Episode (MVE), I almost went with something more structurally typical, but I think in the “big picture,” this is the one you remember most from Three.

06) Episode 57: “Coffee And Commitment” (Aired: 01/04/01)

Will and Grace argue about acting like a couple as they attend Joe and Larry’s wedding.

Written by Adam Barr | Directed by James Burrows

Admittedly, I considered selecting this offering as MVE, for despite some conventional contrivances that go without explanation, it’s a very funny outing that deals with the thesis and reinforces both key relationships and themes throughout the series, showing its identity well. The bulk of the action takes place at Joe and Larry’s wedding — yes, it’s a gay wedding, which is thematically important to this show and its legacy as a mainstream vessel for humanizing characters whose experiences would be deemed niche by MSTV’s broad audience base — and concerns Will’s fear that he and Grace act like a married couple, which is an exact narrative use of the show’s central drama, as the characters’ love for each other, as we know, yields an unhealthy codependence that jeopardizes their chances of ever getting what they want — true rom-com love and happiness. And though the centerpiece at the wedding, where they read a quote and make it about themselves, is silly, I don’t think it’s difficult to buy. (They’ve been self-centered at weddings before; remember the first season finale?) Meanwhile, there’s some big laughs in the subplot, as Karen tries to get Jack off caffeine after he becomes addicted… only to find the figurative shoe on the other foot when Joe/Larry’s wedding turns out to be alcohol free, putting them both in withdrawals. Their slap fight is iconic — I think the funniest bit these two might have ever done — and a definite high note of the season.

07) Episode 58: “Swimming Pools… Movie Stars” (Aired: 01/11/01)

Will and Grace pretend to be interested in Sandra Bernhard’s apartment.

Written by Katie Palmer | Directed by James Burrows

Sandra Bernhard guest stars in this installment that I theoretically don’t like having to praise, even though it’s certainly a success, especially on Will & Grace‘s emerging terms, where the strength of its comic ideas is the primary determinant when scoring episodic value. In other words, “Swimming Pools… Movie Stars” is an entry mostly enamored of its story choices (which is not my preference), but because this design resembles a lot of what’s going to be featured here over the next few weeks, I can’t ignore an example that’s far above average. Accordingly, while the A-story where Will and Grace pretend to be in the market for an apartment just so they have an excuse to hang out with a celebrity is little more than a Victory In Premise that would work with any two characters and any star they were depicted as worshipping, it’s hard to deny both how memorable the idea is and how successful the teleplay is with laughs — as usual with this series. Also, though the B-story maybe forces the Karen caricature into a scenario that only highlights some lacking depth, it also tries to provide added humanity in the process. In this regard, what looks to be a plot only interested in comic opportunities ends up striving to do more on behalf of character. And that’s a great way to look at Season Three, which probably does these idea-led shows better than any other.

08) Episode 60: “Brothers, A Love Story” (Aired: 02/08/01)

Will learns that Matt is in the closet at his new job.

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

Will’s short-lived relationship with Matt comes to an end in this half-hour, with a script surprisingly co-credited to the series’ creators. Although the two typically have their names on the biggest narrative turning points from the first few years — like premieres and finales — I wouldn’t have expected them to pen this offering. The fact that they did actually makes me view it differently, for what could simply be considered the end of a brief arc with one of Will’s love interests now seems to be something more: a romantic failure more tied to the character’s own journey than the story itself… In this study, where hindsight tells us Will won’t be serious about anyone again until Vince (in Six), his dating a closeted man comes to mean so much more, as the depiction of his comfort with his own sexual orientation has not always been optimistic — heck, there are times when it’s bordered on self-loathing. So, the drama of Matt refusing to come out of the closet to his boss while at the seafood shack — where the Karen subplot dovetails nicely for a big joke — then takes on added meaning, given the irony: Will fell for someone afraid to admit who he is; maybe that’s because Will is, too… Now, I could be reading too deeply, but Will gets far less thesis exploration than Grace — as these next three years prove absolutely — so any time the show aims to flesh him out beyond normal episodic subplots, I take extra notice. And I think Kohan and Mutchnick’s credit suggests that intention here.

09) Episode 67: “The Young And The Tactless” (Aired: 04/26/01)

Grace argues with her neighbor as Karen dumps her mother-in-law on Jack and Will.

Written by Jeff Greenstein | Directed by James Burrows

Opening up May Sweeps is an episode that launches another romantic arc by introducing Woody Harrelson as Nathan, who’s obviously positioned from the top of this half-hour as Grace’s new love interest. The gag of her returning to his door over and over again to tell him off becomes a bit strained the more times it happens, but the fresh characterization of Nathan, who challenges Grace and forces her to react in ways different than she ordinarily would — a.k.a. grows and expands the character, which is wonderful — makes their scenes vibrant. And the fact that he seems to have a quirky personality that keeps him from being the bland “knight in shining armor” that most guest paramours happen to be in these MSTV rom-coms (see: Leo), is all the more exciting… Now, the subplot, of Karen dropping her mother-in-law off with Jack and Will, who take the old lady to a gay bar, is probably funnier on paper than it ends up being in its execution, but it’s an affable notion that doesn’t necessarily make any missteps with the characters and their actions. (Everyone’s on point here.) So, it’s an okay companion to the more laudable A-story, which is vital to the year’s progressive use of Grace.

10) Episode 69: “Last Of The Really Odd Lovers” (Aired: 05/10/01)

Will and Grace both hide their new relationships from each other.

Written by Kari Lizer | Directed by James Burrows

Following an episodic story that didn’t include Nathan, this entry picks back up where the one discussed directly above finished, as Grace is now dating him… but secretly, because she’s embarrassed by his lack of refinement. Happily, there’s thematic cohesion as Will is facing a similar dilemma: he’s dating a much younger man and is too embarrassed to tell Grace. The conflict comes not only from their desire to keep the other from finding out about who they’re individually seeing — an interesting conundrum because of the thesis, which posits them as a couple who love each other but can never be together, therefore making their shame about their sexual partners an unhealthy side effect of this codependent relationship — but it also comes from Karen’s discovery of their mutual secrets, which they’re both afraid she’ll spill… Meanwhile, there’s a very funny subplot with the return of Molly Shannon as Val, who gets to interact one-on-one for the first time with Jack, as she becomes a stalker/fan of his cabaret show. Frankly, her inclusion here isn’t quite as superlative as before — there’s far less dramatic substance — but the physical bit they do where he tries to push her out of his apartment is a delight, just as Shannon’s work always is on this series. A fully enjoyable offering.


Other episodes that merit mention include: the first half of the season finale, “Sons And Lovers (I),” which has the functional goal of getting Will and Nathan to bond but does so within a pretty funny and tight teleplay, both parts of “Cheaters,” an initially supersized offering that’s been split in syndication with added footage and introduces the hysterical Lesley Ann Warren as Will’s dad’s mistress, along with two shows that are pretty solidly comedic and make use of the central Will/Grace drama: the season premiere, “New Will City,” and the sweet “An Old-Fashioned Piano Party.” Of more Honorable Mention are three gaudy shows: “Crazy In Love,” with a comedic premise that stretches too much credulity, “My Uncle, The Car,” which shamelessly features Ellen DeGeneres as a nun, and “Alice Doesn’t Lisp Here Anymore,” which loves its premisey one-joke A-story.


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

“Lows In The Mid-Eighties (II)”



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

14 thoughts on “The Ten Best WILL & GRACE Episodes of Season Three

  1. glad u like the flashback show to . it make me laugh with the karen scenes . and i like the sweet end wit will and grace .

  2. Totally agree with you about Nathan being a well defined character and great for Grace’s own growth in comparison to her other boyfriends like Leo (who I also hate!)

    Also really enjoyed your stuff on the Patrick Dempsey arc. I hadn’t realized he was Will’s most serious relationship prior to Vince. I’ve always liked his episodes but that makes me look at it differently too.

    Oh and I’m glad you picked the Cher episode buy whoo boy is it ridiculous.

  3. The Coffee and Committment episode is hilarious. That slap exchange between Megan and Sean is one of the funniest things Ive ever seen on this series!! Thanks for mentioning it.

    • Hi, Eboni! Thanks for reading and commenting.

      That’s one of my favorites as well. Considered it for the year’s MVE.

  4. I’m glad to see that you included the Cher episode. It is one of the show’s funniest, and Cher has brilliant comic timing.

  5. This is my second favorite season but I definitely prefer S2 for all the reasons you so eloquently stated.

    I think the Cher episode is a great example of why S3 is not as strong. I know it’s popular but it’s really not a character driven show in the way that S2’s classics are. And it’s not the funniest. I mean, I don’t think it’s UN-funny, but the laughs are easy. You know?

    I totally agree with you about Nathan though. Harrelson brings a totally different energy tot he show and unlike Leo, we get to know Nathan a bit. He actually has a character. And his episodes next season are some of my favorites from S4.

    Great work as always!

    • Hi, Nat! Thanks for reading and commenting.

      I agree — “Gypsies, Tramps, And Weed” is not a great character-driven entry and I wouldn’t call it the funniest. But I think it’s memorably funny with loud stories and an ostentatious cameo that makes the episode itself represent exactly what the series was becoming.

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