The Ten Best WILL & GRACE Episodes of Season Two

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.

As suggested last week, I consider the second season of Will & Grace to be the series’ strongest collective showing, and while we regularly see sophomore years hailed on this blog as superior — they’re often the most ideal intersection of premise novelty and character knowingness — the idea of any long-running show peaking this early is always one we don’t want to believe, for that means there are more years after the peak than before it. But Will & Grace was established with such a rich dramatic premise — the relationship between its two title characters, and the central conflict of their impossibility as a couple, which makes their lingering fixation on each other detrimental to the individual pursuit of romantic happiness — that we want to see it well-utilized. And, fortunately, Season One showed us that it was possible to use this thesis in stories that were also engaging and funny — creating a template for success that we’d naturally expect the rest of the run to maintain… And yet, the unfortunate inevitability of series television is that, the longer any show runs — and the more episodic story it’s forced to produce — the harder it becomes to explore any dramatic thesis in ways that remain fresh and exciting, for unless there are significant changes that inspire more narrative options, it’s impossible to probe the central drama — the most satisfying drama— with the same consistency as previously enjoyed. What tends to happen then is either the characters regress so previous dramatic beats can be repeated, or their forward progression becomes a sidelined concern — resumed just occasionally, and usually only in big pivots during Sweeps… Both of those tactics are deployed by Will & Grace — particularly the latter, which, as we’ve seen, is a fundamental tenet of NBC’s Must See TV philosophy, where commercialized interests often lead to distractions that don’t necessarily serve the characters (casting stunts, narrative gimmicks) and sometimes even harm them (story-led developments, sweeps-delayed progression). We’ll see this a lot once the series moves, in Season Three, to the network’s prime MSTV Thursday block.

The good news now is that we’re still on Tuesdays at 9:00, where MSTV pressure was felt — see: Joan Collins as Karen’s intended rival or the self-conscious gay kiss episode — but certainly not as nagging as it would become in Three, where tricks increase and the character focus is minimized… That’s a critical reason Two is special though, for while the year maybe doesn’t have as many stories about the dramatic thesis as One (and the ones it has, frankly, aren’t as funny as the baseline), it still uses it as a foundation — best evidenced by the decision to have Will and Grace acknowledge the drawbacks of their codependency by living across the hall instead of together. This embedded design suggests emotional evolution, and given that Two thrives for deepening and exploring every regular (i.e., Will has a new job with a new boss — Gregory Hines — who eventually becomes a love interest for Grace; Jack finally comes out to his mom; Karen’s home life becomes fodder for story), while avoiding the caricaturization that tends to occur later, the year therefore feels like a TOTAL character victory. Furthermore, it offers the most perfect reflection of the series’ identity, for the very thing we’ll most enjoy in later years — the big laughs soon to become the show’s primary selling point — are already on display here. In fact, I’d say Two has three of the funniest episodes of the entire run — “Das Boob,” “Homo For The Holidays,” and “Girls, Interrupted” — proving that it’s just as comedically competitive as any upcoming season. And, again, note that these gems only use the dramatic thesis peripherally, but because Two prizes character progression — even within gaudy story-driven arcs like the Jack/Rosario marriage, which nevertheless works because it fortifies the Jack/Karen bond — these outings also feel dramatically sound in a way that’ll become rarer when MSTV-inspired distractions become more prominent… So, Season Two — which, incidentally, won the series its only Outstanding Comedy Emmy — is the perfect blend of growth and hahas, with few of the drawbacks common to future years. And I’m thrilled to present my picks for the ten episodes that I think best exemplify its strongest.


01) Episode 23: “Guess Who’s Not Coming To Dinner” (Aired: 09/21/99)

Will and Grace adjust to living across the hall from each other.

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

Will & Grace has hit-and-miss premieres, but that’s typically because they have to deal with the aftermath of their prior cliffhangers; and with concerns that are largely story-centric, the plots then becomes the determining factor in how enjoyable these openers — which are otherwise well-written and joke-heavy — happen to be… Fortunately, because Season One’s finale concluded with a premise-specific encounter between Will and Grace, during which they decided to live apart, Two’s debut is set up to further this inherent progression in their relationship. Thus, as Grace moves across the hall and struggles to throw a dinner party (on the floor, for Rob, Ellen, and party crasher Karen) without Will, the story smartly utilizes the central drama of their codependency, and when both find that this arrangement is good for them — even though they’ll still rely on each other a lot because, hey, they’re only several feet away — it feels like both characters are evolving. This sets the stage for the new year, which has fewer explicit thesis-related entries — at least, fewer that are dramatically fresh and forward-moving, like this one — but boasts this invaluable foundation of evolution as constant support.

02) Episode 25: “Das Boob” (Aired: 11/02/99)

Grace artificially enhances her bra size to impress an old crush.

Written by Jhoni Marchinko | Directed by James Burrows

One of the funniest episodes ever produced, “Das Boob” is seminal for both the cultivation of the series’ sense of humor and the audience’s awareness of just how crucial the work of this esteemed ensemble will be in sustaining the show, regardless of its dramatic health. In other words, like all three of the aforementioned gems housed in this collection, this installment doesn’t really concern itself with the central Will/Grace drama. Rather, that’s a peripheral concern suggested only through Grace’s romantic foibles, which her love and reliance on Will typically hinders. In this case, though, she’s hindered by a situational contrivance — a picture in the paper that makes her breasts look much larger than they are. It’s a premise-driven notion, yes, but the character’s insecurities, and the others’ catty remarks, propel Grace to the comedic climax in a very believable way, crescendoing, in sitcom fashion, to a centerpiece with Scott Patterson, a water-filled bra that springs a leak, and some physical comedy that posits Messing as a game slapstick-tician, elevating plot concerns with a capable comic boldness. It’s a comic boldness that’s matched by all three of her co-stars, including joke-peddling Karen and the guys, whose relationship is strengthened here with an amusing subplot, all of which goes on to cement Will & Grace as a show that not only wants big hahas as a regular part of its equation, but maybe as the most important part of its equation — as that’s something this cast, no matter the story, is going to try their hardest to deliver… with regular success.

03) Episode 26: “Whose Mom Is It Anyway?” (Aired: 11/09/99)

Grace is upset when her mother decides to play matchmaker for Will.

Written by Alex Herschlag | Directed by James Burrows

Debbie Reynolds makes her second annual appearance in this half-hour, which, if I’m being honest, probably doesn’t showcase her as well as her Season One debut (last week’s MVE) did, simply because her larger than life characterization was there used as the catalyst for a funny, but dramatically inspired rumination on the series’ central conflict between Will and Grace. This outing, though — despite continuing to build on the relationship established last time between mother and daughter (smartly, effectively, and comedically), and even making time for a Will/Grace drama that somewhat suggests their typical narrative issues — does all this without making the direct link between the guest character and the show’s premise, rendering its story less ideal… Now, that’s merely to explain why her first appearance is untouchable, not as a knock to this entry itself, which, as it turns out, is one of the year’s strongest — and definitely the second best for the Bobbi character, both thanks to those above-noted character elements, and to a teleplay that embraces her characterization, allowing it to dominate better than in any future scripts, which have stories that limit her potency. Also, the Jack subplot with Rosario and the INS agent he once dated is idea-led, but terrifically, unapologetically hilarious.

04) Episode 29: “Homo For The Holidays” (Aired: 11/25/99)

Jack’s friends want him to finally tell his visiting mother that he’s gay.

Written by Alex Herschlag | Directed by James Burrows

My pick for Season Two’s Most Valuable Episode (MVE), “Homo For The Holidays” — which got to air in a special Thanksgiving Thursday slot behind Frasier — is tops for more than just the big laughs that earned it mention among a trio of the year’s previously cited funniest… It’s also a strong, ensemble show with a tight narrative that gets all four of the regulars together at the same time and place for a one-act play that both showcases the series’ extravagant sense of humor and the brilliant interplay of its smart cast, all the while offering a plot that, again, may not be directly connected to the show’s central Will/Grace drama, but relies on thematic interests unique to Will & Grace. That is, the premise, of the seemingly comfortable-in-his-own-skin Jack having not told his mother (Veronica Cartwright) a fundamental part of his identity — that’s he’s gay — is not only comedically ripe, given how flamboyant Jack is depicted (in relation to Will), but dramatically rich too, because this is a dilemma that every gay person knows, and even those that aren’t, can understand it. Furthermore, the interactions among the core cast are used ingeniously to exacerbate both the humor and the stakes — as Jack’s lie about having once been in a serious relationship with Grace sparks the latter and Karen into a one-upping feud, and Jack’s dynamic with Will, who was pressured to come out to his family by Jack, is what ultimately convinces the man in question to finally be honest with his mom (who has a secret of her own: the man Jack thinks is his dad isn’t biologically so). This is precisely the kind of story that Will & Grace was made to tell, and for that reason, despite the lacking central conflict, a show like this is as much a reinforcement of the series’ premise as any thesis story, especially when it comes packaged to these big laughs and great performances. (Note: Sean Hayes won an Emmy for his work here and in “Acting Out.”) An easy choice for MVE.

05) Episode 31: “I Never Promised You An Olive Garden” (Aired: 12/14/99)

Will and Grace lie to avoid hanging out with Rob and Ellen.

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

There was room on this list for one of the two Rob/Ellen shows to be featured (not counting the premiere, in which they appear, but not crucially). My feelings on them are complex. I basically find the pair a functional presence that the series only uses opportunistically — when it needs a circle of friends, or aims to highlight the Will/Grace bond by revisiting game night — and that, even though they have a modicum of definition, they just aren’t comedically on the same level as the regulars… However, I also think the couple is a benefit to stories that flesh out the leads’ shared history (like next season’s flashback), and that there’s nothing wrong with having a “functional” group of friends outside the leads — Joe and Larry will join these ranks next year — primarily when this couple design mostly just reiterates that Will and Grace behave like a couple, which speaks to the thesis. So, while Rob/Ellen outings may intrinsically be less desirable, they do have dramatic relevance, especially in Two, which doesn’t contain their greatest number of appearances but affords them their greatest prominence, as the show continues to try evolving the non-cohabitating, yet still couple-acting, Will and Grace, and therefore uses their best “couple friends” to its choice subliminal advantage. As for why this is here and the other — “An Affair To Forget” — is not, I think the farce is better maintained in this one’s A-story, and the B-story, of Jack bonding with a boy at Karen’s step-kids’ school, is good for his character and thus a more desirable subplot than the alternative.

06) Episode 32: “Tea And A Total Lack Of Sympathy” (Aired: 01/11/00)

Jack and Grace hope to appear on an antiques show, as Will tries to get Karen’s business.

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

As briefly discussed in last week’s list, the most common episodic pairings are either Will/Grace and Jack/Karen or the guys and the gals, so any time this is inverted and we get Jack/Grace and Will/Karen is worth our attention — particularly at this point in the run, where it’s a rarity and the characters’ usage is such that we can expect some choice comedic interplay (not dependent on story). Wonderfully, this installment maximizes both pairs — offering some broad, but not unearned, guffaws in the otherwise premise-led Jack/Grace story in which they go down to a taping of an Antiques Roadshow knock-off with an item they’re sure is cheap, but are shocked to learn is actually valuable. It’s a chance for two of the show’s biggest clowns to clown, and it’s just a joy to see them together… Meanwhile, as Will’s boss, Ben, forces him to try landing Karen’s husband as a client at the law firm, the Will/Karen story is used to significantly strengthen their relationship, and not only is it successful in doing so, it also wiggles in big laughs that match the calibre of what’s going on in their counterparts’ plot. In this regard, I consider this both a fully enjoyable entry and a notable one, for developing key relationships.

07) Episode 35: “Oh Dad, Poor Dad, He’s Kept Me In The Closet And I’m So Sad” (Aired: 02/15/00)

Will’s father tells all his colleagues that Will and Grace are married.

Written by Katie Palmer | Directed by James Burrows

There’s a unifying theme to this excursion that elevates it above the ranks of the below Honorable Mentions, which all typically have one good idea and a fairly good execution, but can’t count themselves as wholly compatible or well-enacted. You see, because this show deals with both gay characters’ relationships with their fathers, there’s a dramatic continuity here that justifies the entire episode’s existence. Of the two stories, the “A” is probably the best remembered, and it’s indeed related to the thesis, for Will goes to one of his dad’s work functions, only to learn that his beloved father (Sydney Pollack, making his first appearance on the series) has been too ashamed to tell his colleagues that his son is gay and has instead told them that Will is married to Grace… a mirror of Jack lying to his parent; now the parent is lying about Will. It’s an appropriate premise for the series, and although it doesn’t quite reach the heights we’d hope — the drama is a little too ham-fisted and the comedic turnaround is big without big laughs — it’s choice fodder for the series, especially when paired with a surprisingly jokey story in which Jack believes Karen has set him up on a blind date with an older man… only to be shocked when he learns that Karen asked them to meet because she thought she’d found his biological father. It’s another premise-y comedic notion, but it’s connected to Jack’s character arc, it brings humor, and when paired with the Will story, it gains value.

08) Episode 36: “Acting Out” (Aired: 02/22/00)

Jack protests NBC after the network cuts a landmark kiss between two gay characters.

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

Referenced above in the seasonal commentary as an early example of a Must See TV-inspired Sweeps gimmick, this installment is a shameless stunt that was timed to garner the show press and increase its ratings at a time when doing so was most critical. It’s atypical (the on-location New York material is jarring), obvious (of course NBC is going to plug its Today Show and have Al Roker appear), and some of the comedy feels forced (the crazy lady in the NBC lobby) or subjugated to the loud demands of these commercialistic desires (the Grace subplot only exists to allow the final Seinfeld-ian dovetail moment)… And yet, because the story involves Jack protesting NBC after it cuts a primetime kiss between two gay male characters, there’s a sense of self-awareness that acknowledges both how the series’ use of its gay regulars makes it the most theoretically “niche” mainstream show on the air and how it’s making a legacy for itself that will certainly be more readily praised in the years to come. Accordingly, the totally predicable and story-led kiss between Jack and Will, which makes this show, presumably, the first guy/guy kiss in primetime TV, can be appreciated as something more important: the certification of the series’ cultural reputation, via the use of elements within its identity to both shake up televisual norms and adhere to the network’s commercialistic intentions all at the same time.

09) Episode 39: “The Hospital Show” (Aired: 03/28/00)

Karen decides to have some fun with her friends after Stan has a health scare.

Written by Adam Barr | Directed by James Burrows

Although I typically see this segment highlighted as one of the season’s funniest, you’ll note that I purposely didn’t include it among the trio of big laugh shows referenced several times above. Don’t get me wrong: I think this is a very jokey entry with grand comedic intentions, and as a matter of fact, I think it absolutely is “comedically competitive” based on the anticipated baseline of humor with which future years (and the show itself) are associated. Yet, I find it obviously story-driven and at times, unappealingly broad — in a manner that, once more, reflects what’s going to become more common from the series, but here, at this point in Season Two, still feels a little out of place… Now, I feel the same way about one of the Honorable Mentions below — “My Best Friend’s Tush” — but, unlike that one, I’m glad to highlight “The Hospital Show,” for a few reasons. First, it’s anchored by Karen and aims to explore the individual relationships she has with the three main leads and Rosario. And seeing as Karen’s really only used for comic reinforcement this year, I appreciate this outing for putting her right in the center of the action and actually making her more emotionally complex by the end of it. Second, it’s got that unity of time and place, as almost the entire show is set at the hospital, making for a theatrical affair that both enables a more heightened comedic style and allows these performers to do what they do best: burlesque. So, it’s classic Will & Grace through and through.

10) Episode 42: “Girls, Interrupted” (Aired: 05/02/00)

Grace tries to befriend her old nemesis, Val, and Jack hopes to revert a reformed gay man.

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

Rounding out this list of the best episodes from Will & Grace’s best season is another one of the half-hours that I’d easily rank among the series’ funniest, with a lot of the same qualities heralded in those already featured above. For starters, it boasts the second appearance of the hysterical Molly Shannon as Val, the one-time “replacement Grace” who got into a cat fight with the leading lady, and every time we see Shannon on this series, it’s a quirky, hilarious delight… That said, as with Debbie Reynolds, I’ve already indicated that Shannon’s first appearance is probably her strongest — it’s more dramatically to the point and concerned with the Will/Grace relationship than any other. This one may actually be humorously on par though, for the idea of Val being, not just prone to violence, but also to kleptomania, offers a bevy of laughs and great scenes (culminating, of course, in another cat fight). Meanwhile, the B-story, while kind of idea-driven, ostentatious, and a vehicle for guest star Neil Patrick Harris (then ending his single-season stint on the MSTV flop Stark Raving Mad), is simply too outrageously funny to ignore, as Jack brings Karen to a group for reformed gay people in the hopes of wooing Harris’ character back to his side. Garnering some controversy after the initial broadcast, this Sweeps subplot nevertheless feels, again, thematically within the show’s wheelhouse — both dramatically and comedically worthy of these characters.


Other episodes that merit mention include: “Terms Of Employment,” which introduces Gregory Hines as Will’s new boss, and claims a silly, but popular Jack/Karen subplot, “Advise And Resent,” which I think affords strong material for both the men and the women in their respective plots (with some key Will moments, in particular), “An Affair To Forget,” which is the year’s other Rob/Ellen outing noted above, providing extra Will/Grace history but a weaker subplot, and “My Best Friend’s Tush,” an overly broad show that has a bizarrely comic A-story with Joan Collins and a taco restaurant, and a Jack/Will B-story that stretches credulity a little too much to be praised. Of more Honorable Mention quality are lopsided shows — with one plot that works and another that doesn’t — “To Serve And Disinfect,” memorable only for the funny Karen porn video (Mullally won an Emmy for her work in this and “Polk Defeats Truman”), “He’s Come Undone,” which has a fascinating A-story that tries to examine Will, but ultimately ends up being more about Grace (which is exactly the problem), and “There But For The Grace Of Grace,” a notable entry with a fun and thesis-related A-story with Orson Bean and Piper Laurie playing a cautionary future example for Will and Grace.


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

“Homo For The Holidays”



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

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

  1. I wish that you had included To Serve and Disinfect. The Karen story is hilarious as you noted, but I also enjoyed the Will/Jack plot in it. What did you find lacking in it?

    • Hi, Charlie! Thanks for reading and commenting.

      I’m glad you asked! I feel strongly about this one. I think *both* stories in “To Serve And Disinfect” are led by their premises, deriving humor situationally with not enough natural character value.

      I actively dislike the Will/Jack plot; it’s another conveniently circumstantial idea — conflict born from plot — that I don’t believe offers the necessary laughs to excuse its unideal design. And its attempted dramatic relevance for Will is so strained that when contrasted against episodes like say, “Oh Dad, Poor Dad…” or even “Advise And Resent” (both of which address the character’s thesis-related emotional arc), it feels even more story-led and unnecessary. It neither reinforces the central drama nor, I believe, the show’s big-laugh reputation (which Will/Jack stories can often do).

      As for the Karen part, I was actually being generous above when suggesting it was strong enough to make its whole episode an Honorable Mention. (I needed to cite it here because of Mullally’s Emmy win. And I *knew* it was well-liked because of this particular subplot, which is certainly memorable.) I actually think it’s a familiar sitcom B-story that enables easy jokes — porn title parodies are always cheap laughs; they have nothing to do with character — and while I like it slightly better than the Will/Jack plot, because it successfully gets all its surface hahas, ultimately…

      In a year where the series is both more comedically creative and has a richer appetite for character development, “To Serve And Disinfect” is not what I’d call a crowning achievement. Right now — and not for very much longer — I can ask for better because it’s in abundance. Stay tuned…

  2. Molly Shannon is a treasure and all the Val appearances tickle me. But this one, with the NPH subplot? *chef’s kiss*

  3. Great list. I really appreciate your astute commentary on Rob and Ellen and I think the two episodes that have them a major part of the story this season are those characters’ best ever-especially “I Never Promised You An Olive Garden” which is really funny because it acknowledges how annoying they are to us and how different they are from Will and Grace. I’m so glad to see it here.

    Also, the Joan Collins episode is memorable but I think you made the right call keeping it an Honorable Mention. It’s a funny idea but the end falls flat. And I think the Subway Tush subplot is just too broad broad broad. It sounds like you agree?

    Can’t wait for S3! That’s my second favorite season!

  4. This is definitely the season with the most gems. No doubt that “Homo for the Holidays” is the top of the top.

    And so happy to see the Sydney Pollack episode here. I think that’s such an important Will episode and I find the Jack story hilarious! I don’t see it mentioned as much as others.

    I’m always curious to ask this when you cover a good season of a good series: What’s your least favorite this season?

    • Hi, Elaine! Thanks for reading and commenting.

      I think the entry with the least value for character is the second half of the season finale, where plot concerns take over — “Ben? Her? (II).” That would be my least favorite.

  5. Megan is so funny with Will in “Tea & a total lack of sympathy” and with Jack in “Girls Interrupted.” Also thrilled you included ‘The Hospital Show”. I dont know why she didn’t pick these for her Emmy shows. They are much better than the ones she did pick imo.

    Anyway good job as usual. I like S3 a lot though so I’m excited for next week too!!

    • Hi, Eboni! Thanks for reading and commenting.

      Yes, Mullally gives some great performances here — especially in the shows you mentioned!

  6. Thanks Jackson, Agree with you on season 2 being the series best and in the trio of classic episodes mentioned and MVP choice. If there is one line I remember laughing like crazy at from during the series entirefirst run it’s Karen’s “What is she headless?” when she finds out Jack’s mom still does not know about his sexuality

    • Hi, Bob! Thanks for reading and commenting.

      Yes, that’s a great joke from an episode — and a series — full of them!

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