The Ten Best WILL & GRACE Episodes of Season One

Welcome to a new Sitcom Tuesday! This week, we’re launching 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.

Let me start by thanking everyone who voted for Will & Grace. It’s proven to be the perfect series on which to end our Sitcom Tuesdays look at the ‘90s/turn-of-the-century. Not only does it embody so much of what we’ve been examining these past few years — particularly in NBC’s Must See TV Thursday shows — but it also reflects many of the themes that would develop in the genre during the first two decades of the 21st century. So much so, in fact, that the 2017 revival — currently in its third and final season at the time of this publication — is perhaps the least aesthetically jarring comeback from this recent wave of ‘90s reboots… But I don’t want to talk about the revival now — I’ll cover it sometime next year, once it’s concluded — and, actually, I’m even going to ask that you pretend the revival doesn’t exist, for despite their creative similarities, these are two different series. The original eight-season run is a narrative work unto itself — it’s got its own beginning, middle, and end, and it exists without any knowledge of the future. Its finale is its finale, and that’s as far as I’m going to let our hindsight bias take us over these next eight weeks…. So, let’s go back to 1998 and stay thereabouts, for Will & Grace is very much a product of that era…. Now, much has been made since the series’ premiere of its cultural legacy — gay regulars in primetime was both a novelty and a risk, especially after the recent failure of Ellen — and our commentary here can’t ignore how much of the show’s identity is shaped by the sexual orientation of its two male leads. It’s relevant to both popularity and even perceptions of quality. Yet I aim to avoid the framework that too often surrounds the series and focuses on the importance of the leads’ depicted sexuality, for while this certainly addresses some of the show’s appeal and has indeed become its guiding raison d’être, this ignores core big picture concerns: how the series managed to exist and even thrive during this turn-of-the-century era and why it’s worthy of discussion as a great sitcom.

To that last point, Will & Grace is worthwhile because it has well-defined characters who earn emotional investment and inspire regular laughter. Their sexual orientations, a tenet of their identities, is part of this — but it’s an ingredient, if you will; not the whole meal. More later, though… First, I want to talk about another aspect of the show’s identity — something often ignored because, well, it’s not all positive: the way the series reinforces its status as a staple of NBC’s Must See TV Thursday lineup. Although initially slotted in a terrible Monday berth, Will & Grace moved up the ranks twice within its first year, graduating to Tuesdays (“MSTV-B”), and then, in the spring, to the hammock spot between the network’s top laffers: Friends and Frasier. It likely would have joined this Thursday lineup permanently if not for the two-year commitment NBC then had with Frasier, which delayed Will & Grace’s move to Thursdays until its third season (2000-‘01). From then until the end of its run in 2006, Will & Grace was a linchpin of the network’s comedic firewall, spending more time in the popular Must See TV block than any sitcom other than Friends. (This is not counting shows prior to 1993, mind you.) It survived there for a variety of reasons, including its ratings, but also because it was willing to adhere to the network’s desired demo-seeking template. Like Friends, Will & Grace featured attractive young pals living (beyond their means) in Manhattan. The optimistic characters wanted little more than to love and be loved, and as with the majority of MSTV hits, it proved to be a weekly romantic comedy, with character arcs existing mostly in the form of relationships… Of course, being one of NBC’s Must See TV comedies — one produced by NBC — also came with strings attached: overtly commercialized interests that could impede quality.

We observed this on Friends, which would resort to narrative gimmicks and casting stunts to gin up the ratings, mostly during Sweeps (when ad rates are set), even crafting arcs around this timetable and delaying or progressing character growth in deference to developments and cliffhangers that existed and/or were used accordingly. Okay, every show has this problem, but there are whole seasons of Friends that suffer from its MSTV mentality (MSTV-itis)… And sadly, Will & Grace is worse. It embraces these stunts and gimmicks with apparent abandon, giving little care as to whether this gaudy cameo (say, Madonna) or that ill-motivated arc (say, “let’s you and I have a baby”) benefits the regulars, or sadder yet, exists at their expense, weakening our faith in their continued, rom-com-led evolutions. Believe me: we’ll see many examples of how being a hit on this particular network at this particular time negatively affects the series’ storytelling — mostly after the move to Thursdays — but suffice it to say now, Will & Grace is, like Friends, a poster child for MSTV, and that’s ultimately why it’s a winning study of the era… However, for as much as Will & Grace resembles Friends, it’s also fundamentally different: it has gay characters and wants to depict them nobly. This is something neither Friends nor Frasier had to worry about, and it comes packaged to both added scrutiny and an inherent novelty that’s fueled a significant part of the series’ value, giving primetime play to a group of people not used to seeing themselves reflected on TV with such humanity. (Yes, humanity — when critics chide the show for its use of surface stereotypes, the fact remains: never before had such multi-dimensional gay characters received so much mainstream visibility.) This last part is why I said Will & Grace, though entrenched in its own era, also foreshadows future sitcom trends.

You see, this current climate (2019) is a “niche buffet,” with a plethora of distributors offering individually tailored content for almost everyone at least, with regard to categorizable elements of identity (gender, race, age, orientation, politics, etc.) — and Will & Grace, for as much as MSTV would allow, is something of a “niche sitcom.” Now, I certainly don’t want to suggest that those categorizations make a work niche because they’re prohibitive to a universal appeal. Rather, it’s that Will & Grace uses elements of identity to provide representation in a way that resembles today’s “niche buffet” market. And in an era where shows like Friends catered to a majority audience and therefore desired easy, and almost total, relatability, Will & Grace is an outlier, as only a fragment of the viewers could explicitly identify with the experience of its gay characters (and only another fragment could count being close friends with someone of that community). Thus, it was, on paper, a harder show to sell to NBC’s audience than a Friends (or even the more rarified Frasier), marking an evolution away from relatability-driven series, towards more experience-driven ones (like we see today). And, to put a button on this, I’d say Will & Grace is the most popular “niche sitcom” of the MSTV era… However, for as much as the series’ inclusion of gay leads makes it special, and even after acknowledging how this important aspect of the characters’ identity is manifested within the series’— the show’s burlesque style of writing, its pop cultural references, and its big-laugh comedic fearlessness all clearly come from scribes who themselves are members of the LGBT community — I’d say the biggest reason for Will & Grace’s commercial popularity and creative viability is the same for every series, niche or not; and I’ll repeat what I wrote above: Will & Grace is worthwhile because it has well-defined characters who earn emotional investment and inspire regular laughter.

At the end of the day, we don’t need to look like, or live like, or even think like characters in order to find them amusing and care about their weekly adventures. (To wit, the sitcom only exists because of diverse and extreme characterizations — the contortion of, or the heightening of, what’s considered “normal.”) And so, Will & Grace actually lives and dies just as you’d expect it would: at the feet of fascinating, flawed primary characterizations who are used well in comedic story… This means, Will & Grace was a hit because of Will and Grace, a pair with a unique, emotional conundrum made clear right from the pilot — they’re two people who love each other and would be together… only they can’t because he’s gay and he’s never not going to be gay. As such, the series is essentially about a doomed romance, for Will and Grace love each other but can never be, and the show quickly realizes here in this first season (the sincerest for character, prior to MSTV-itis) that this dynamic may actually be unhealthy. That is, their unconsummatable love for each other limits their ability to find romantic success elsewhere, which, as in all rom-coms, is the measure of their emotional maturations. This makes for a rich central conflict — a universally relatable one — as the show, and the audience, needs their regressive, codependent relationship to continue, not just to feed the comedy, but to sustain the series’ premise, even though the characters need the opposite. And yet, lest we worry about the premise and the characters being in opposition, let me remind you that we only care about a series because we care about its characters, and what they need is what we need, so this tension is welcome… Still, there are whole years where this is not well-modulated, as the show becomes story-driven and either shies away from their drama or forces it inorganically.

Additionally, no matter how natural McCormack is, or how adept at physical comedy Messing proves herself to be, or how brilliantly James Burrows stages their one-on-ones, the show has to find its big hahas elsewhere… Enter Jack and Karen, two fan favorites less concerned with emotional growth (they don’t have to worry about the blowback that happens when they don’t get it) who basically only have one purpose: increase the laugh quotient. They’re complementary to the main couple — another big factor in the show’s popularity — and though we’ll talk more about the ensemble throughout these lists, I’ll note that the cast is probably the series’ strongest suit; they’re a well-oiled machine without a weak link. That’s important, for, creatively, the show peaks rather early, as the thesis’ character concerns — on display for much of Season One — tend to get undermined by both the MSTV side effects that kick in following the move to Thursdays, and the series’ rapidly heightening sense of humor, which sometimes asserts itself as more important than the characters’ arcs. In other words, then, the best seasons of this show are the ones that balance those other interests with character material that stems from the series’ dramatic thesis. (Spoiler: by this definition, Season Two is the strongest; stay tuned…) As for Season One, the show’s sense of self is established fairly quick in the run, and there are clear victories whenever it explores the ensemble — either getting them all together or switching up the pairings. However, early episodes are dogged by an unnecessary regular — Will’s client Harlin (Gary Grubbs), who’s almost impossible to involve in story with the rest of the cast — and it isn’t until February of 1999 that the series finally clicks. Here, the show moves out of its discovery period and begins producing narratives that are motivated by the characters and come close to matching the high-octane comedic sensibilities with which the series is now associated. The “back nine,” then, are Golden Age adjacent, offering some of the best episodes of the series’ entire run. So, I’m happy to share ten of my selections for this season’s finest.


01) Episode 1: “Pilot” [a.k.a. “Love And Marriage”] (Aired: 09/21/98)

Grace’s boyfriend surprises her with a marriage proposal.

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

As with most of the classics we cover here, Will & Grace‘s pilot is an excellent mission statement for the rest of the run, establishing the core relationships and supplying a dramatic thesis that will carry the characters through to the series finale. With a comedic rhythm fairly well-established, and a good understanding of the primary players — save Karen, who’s going to become a much bigger personality very shortly — there’s something almost assured and appealingly confident about the script, as if this is the show Kohan and Mutchnick were born to write… The crux of this opener, and the rest of the series, is the central relationship between Will and Grace, and the teleplay does an outstanding job of illustrating their bond — the Pyramid game is a great example of “showing, not telling” (and it even introduces us to Rob and Ellen, two characters who see a fair amount of use in these first few seasons) — while the almost-wedding is a perfect rom-com cliché that lets us know what the show emotionally aims to be (and that it fits NBC’s brand), and leads to the wonderful final scene, where the central conflict is stated: Will and Grace are lovers who can never be. And away we go…

02) Episode 2: “A New Lease On Life” (Aired: 09/28/98)

Newly single Grace wants to move in with Will.

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

The series’ sophomore outing is already an improvement over the pilot, for while the show was dramatically well-premised within its premiere, it now goes about developing some of the elements that will be crucial to its weekly operation — primarily with the ensemble (which, at this point, still includes Harlin, a character the show toils to have interact with the other regulars). I consider this an especially triumphant installment for solidifying the Will and Grace relationship, as the chemistry between McCormack and Messing truly takes on a life of its own now, demonstrating a fresh, playful, believable give-and-take that’s honestly unlike any of the central sitcom duos’ of the era. Scenes like the one in Grace’s apartment in Brooklyn, which give Messing the chance to demonstrate her willingness and ability with physical comedy, go a long way in making Will and Grace more than just dramatically interesting — now they’re capable of anchoring and propelling comedic stories, too. Meanwhile, the entry also sees the first meeting of Jack and Karen, two characters who blossom when in each other’s presence — as already evidenced here. They will go on to make some of Will & Grace‘s funniest moments, and their first meeting is just that: the first. So, this is a seminal half-hour for the series.

03) Episode 7: “Where There’s A Will, There’s No Way” (Aired: 11/16/98)

Grace fears that Will is the reason for her lackluster love life.

Written by Jhoni Marchinko | Directed by James Burrows

I seldom see this one listed among the year’s finest, and if you wanted to pick another from this point in the season — after the first few offerings, but prior to the more consistently sharp “back nine” — you’d probably go for a show with a story that’s more intrinsically comedic (i.e., a Victory In Premise). But I think this is an important stepping stone in the series’ exploration of its dramatic thesis, as it’s the first to tap into the idea that Will and Grace’s dynamic, which we already love and recognize as the series’ grounding force, may actually be counterintuitive to their forward progression as characters, particularly Grace’s, whose pursuit of love in the wake of a failed engagement is the driving engine of this first year (heck, the first five years). That is, this is the point in the series’ run — and note how early it occurs — where the central conflict is contextualized within the genre’s broader need to ensure the evolution of its regulars, as the dilemma goes from theoretical to practical: as long as Will and Grace remain as codependent as they are, neither one (but primarily, at this moment, Grace) will be able to ultimately get what they want. And, as we started to discuss above, that’s a fascinating font of drama and comedy, because it reinforces the characters’ flaws through something that should otherwise be appealing — their charming, darling, lovable relationship (which, again, is what sustains the series).

04) Episode 13: “The Unsinkable Mommy Adler” (Aired: 02/09/99)

Grace’s mother visits with a suggestion — Grace should marry Will.

Written by Alex Herschlag | Directed by James Burrows

My choice for the year’s Most Valuable Episode (MVE), this is the moment I alluded to above — the point in the show’s first year where everything finally seems to “click.” The characterizations have not only been established, but they’ve also had time to settle and adapt to regular narrative usage, meaning that they’re fully functional, with well-known POVs that don’t have to be motivated by story. Part of this ascension to consistent excellence happens because earlier entries have done the work — bringing the foursome all together and exploring the possibilities of pairing opposites: Will/Karen and Jack/Grace — but it’s also because the show is now confident enough to unleash its full comedic potential. It can be as outrageous as it wants — take a gander at Debbie Reynolds’ larger-than-life portrayal of Grace’s mother, and see what I mean — for it has a solid character foundation in support… As for this outing in particular, it’s notable for more than just the terrific use of Reynolds (perhaps the show’s first stunt casting — although this one’s more textually sincere than others; it’s no winking cameo), it’s also got an intelligent premise, which exploits Grace’s flaws while addressing the central conflict, for Bobbi’s desire to see Will and Grace together once again forces the regulars to acknowledge the tragic irony of their relationship. Never again is Bobbi used so well — to the benefit of outstanding weekly comedy and the series’ larger dramatic interests… Meanwhile, the Karen subplot (she has a pregnancy scare) won’t win any points for, well, anything, but it’s a tactic to deepen her otherwise jokey character and I think that’s vital to the aforementioned “click,” as now everyone can be called upon for earnest, real moments. It’s a gem.

05) Episode 15: “Big Brother Is Coming (II)” (Aired: 02/23/99)

Grace tries to keep Will from finding out that she slept with his brother.

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

Will & Grace‘s first February Sweeps continues with a notable two-parter (spread over two weeks) that casts John Slattery as Will’s estranged brother, with whom he hasn’t communicated in years. It’s a worthwhile story because it gives depth to Will, who, frankly, has thus far been emotionally subordinate to Grace (even though he’s been the narrative anchor — it’s his apartment that’s the center of the action). And it also helps build a shared history both for the brothers, and for Grace, who’s like family to Will — a theme that will come up frequently throughout the series, especially as all the regulars’ family members become a more prominent presence… Now, truthfully, I could have put either Part I or Part II here; Part I sets up the conflict between the Truman boys and uses Jack’s birthday party as a centerpiece where all the characters can congregate for the drama — it’s effective and smart. But I give the edge to Part II because it twists the conflict and refocuses it onto the Will and Grace relationship, which is closer to the dramatic thesis, for once Grace sleeps with Will’s brother, it’s a whole different can of worms with more emotionally exploitable and comedically ripe ramifications for the characters. And that’s why, although I recommend both parts, only the second makes this list.

06) Episode 16: “Yours, Mine, Or Ours” (Aired: 03/02/99)

Will and Grace are both interested in the same man.

Written by Ellen Idelson & Rob Lotterstein | Directed by James Burrows

Of all the outings featured on this week’s roster, “Yours, Mine, Or Ours” is the one best classified as a “Victory In Premise,” for it utilizes a story that, simply on the basis of its log line alone, works for the two central characters — putting them in a conflict that tips its figurative hat to their core drama, without hitting it as hard as other entries this year do. By having the two characters in competition over the same man, the story is able to recognize how ideally matched Will and Grace are for each other (and the McCormack/Messing chemistry is truly why this one goes from being merely a good idea to a good episode), while simultaneously addressing the very reason they can’t be together: they both like men. Furthermore, Will & Grace‘s comedic identity is well-featured in the mystery surrounding the man in question’s sexual orientation, for as we noted above, that’s a regular theme that distinguishes the series from its contemporaries, and it gives play to the idea that, contrary to the way some characters may behave, one’s preference is not always so obvious. (And maybe there is no preference.) In this regard, it’s not just a primo story for the characters… it’s a primo story for the show, too.

07) Episode 17: “Secrets And Lays” (Aired: 03/23/99)

Grace takes Will and the gang up to a snow cabin to distract him from a sad anniversary.

Written by Dava Savel | Directed by James Burrows

Although I would classify the first season as being among the series’ finest — either the second or third best (if I could consider the “back nine” of the first season a separate entity, I would put it second, behind only Season Two) — it’s not yet possible to make a list of ten offerings that I find completely and totally stellar. I mean, there’s room for a good-but-not-great show that does a lot of the right things — like get the four main characters together within a story that works well for the central couple, exploring the key dramatic issue of Will and Grace’s codependence on each other being an impediment to her personal arc of finding love and getting a rom-com happy ending — but still doesn’t manage to be as comedically competitive as most, for some of the humor is more situational than this year’s best. And, being that this presages more of the idea-driven fare that’s to come within this series’ storytelling, it, even with its sincere dramatic implications, almost feels like a later-season story that lacks the later-season laughs… Nevertheless, this collection of Season One’s “greatest hits” benefits from another segment that addresses the thesis well and continues to build the ensemble’s bond.

08) Episode 18: “Grace, Replaced” (Aired: 04/08/99)

Grace is jealous when Will gets a new friend who acts exactly like her.

Written by Katie Palmer | Directed by James Burrows

Despite picking “The Unsinkable Mommy Adler” as the year’s MVE — for its supreme use of the thesis in an episode that truly embodied the first time everything “clicked” into high gear, making it therefore a series milestone — I think “Grace, Replaced” may be the year’s funniest excursion. And while that might be the guiding reason to pick my favorite in future years — when Will & Grace doesn’t have much solid arc-progression and instead is best celebrated as a string of bawdy jokes held together by a well-oiled machine of an ensemble — the nature of Season One is such that dramatic use of the central conflict is an important determinant of its episodic success… To that point, though, “Grace, Replaced” is no slouch either; it may not directly concern itself with the central dysfunction, but it uses the relationship to zero-in on Grace’s insecurities, all the while making room for Messing to showcase her slapstick prowess. It comes courtesy of the Lucy/Ethel “Friendship”-inspired cat fight between Grace and her “replacement” (the Pyramid game is used brilliantly, again, to make that point), Val, played by the hysterical Molly Shannon, who enlivens every one of her appearances, but like Debbie Reynolds, is never used quite so narratively effectively as here, when she really gets under Grace’s skin. It’s hilarious — as with the MVE above, this is an undoubted classic.

09) Episode 19: “Will Works Out” (Aired: 04/22/99)

Will is embarrassed by Jack at the gym.

Story by Michael Patrick King & Jon Kinnally & Tracy Poust | Directed by James Burrows

If the most common structure of a Will & Grace script has the two titular leads in the A-story and high-octane haha-generators Jack and Karen in the subplot, then the second most common structure splits the foursome up by gender — having the guys in one story and the ladies in another. “Will Works Out” is the best example of the latter from this first season, with an amiable B-story for Grace and Karen that finds the two bonding over drinks (anything that strengthens Karen’s relationships with the other members of the ensemble is definitely welcome, since she’s locationally the farthest away from everyone else and easily the hardest to wrangle into story), and a dramatically rich main plot that explores Will’s somewhat tragic view of his identity — his sexual orientation, in particular — that’s exacerbated by Jack, who, unlike Will, is much more comfortable being flamboyantly himself. It’s, well, not a laugh riot… but it’s an honest and human look at Will and the inner obstacles standing between himself and his own happy ending, making it one of the more potent character studies on this list.

10) Episode 22: “Object Of My Rejection” (Aired: 05/13/99)

Grace reunites with her ex-fiancé and Jack agrees to marry Karen’s housekeeper.

Written by Adam Barr | Directed by James Burrows

Admittedly, the first year’s finale isn’t one of my favorites, for it already encapsulates many of the big development story-heavy qualities that will preclude most of the series’ season-enders from making my lists (especially once MSTV-itis is in full swing). Additionally, while I celebrate the show’s first use of Rosario, a fantastic peripheral character who makes Karen more interesting and is always an additive when it comes to a scene’s humor level, the whole idea of two characters marrying so one can stay in the country is a story-driven sitcom contrivance that typically has little to do with their definitions. That’s true about “Object Of My Rejection,” and the whole centerpiece, with Will and Grace making a scene during the ceremony because they’re really arguing about themselves, is as trite as any third act of a mediocre rom-com. But, in this case, I think the Rosario/Jack story actually begets some funny material in Season Two, and since Jack’s larger-than-life persona makes his marriage to Rosario almost patently absurd, the laughs overwhelm the story concerns. Also, with Will and Grace embroiled in a plot that cements the year’s established conflict — ending with their decision to stop living together, a quintessential pivot in their dynamic and the show’s depiction of it — the falsely predicated wedding has obvious thematic value to the thesis and these characters.


Other notable episodes that merit mention include: “Big Brother Is Coming (I),” the first half of the Truman brothers’ two-parter, and “Will On Ice,” which hangs a lantern on the cultivation of a bond between Jack and Grace and gets the foursome together for a centerpiece that I wish was bigger. Of more Honorable Mention quality are three entries with funny ideas: “The Big Vent,” “My Fair Maid-y,” and “Alley Cats.”


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

“The Unsinkable Mommy Adler”



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

12 thoughts on “The Ten Best WILL & GRACE Episodes of Season One

    • Hi, BB! Thanks for reading and commenting.

      Yes, it’s one of the show’s best years — you should check it out!

  1. Some really brilliant episodes here. “Mommy Adler” is a classic. And I agree that Season 2 is the best. Looking forward to next week.

    Great job as usual!

    • Hi, Nat! Thanks for reading and commenting.

      Yes, next year’s got the greatest number of classics — it’s the WILL & GRACE list you don’t want to miss!

  2. Debbie Reynolds is so good in her episode this season! I love her S2 appearance as well but none of them come close!

    And all the Molly Shannon episodes are great. She cracks me up.

    Are you a fan of Rob and Ellen? I like that they exist and are sometimes convenient but I’m not sure they ever really get to participate meaningfully in a classic episode.

    • Hi, Elaine! Thanks for reading and commenting.

      I appreciate Rob and Ellen because they give history to the Will and Grace relationship and their inclusion often times is connected to the series’ dramatic thesis. Comedically, however, I don’t think they get many chances to be as competitive as some of the series’ other recurring presences.

  3. Megan Mullally is my QUEEN! I’m totally on her side in this feud!!! (Not a Messing fan).

    This isn’t one of her best seasons but just looking at some of the pictures with here here is cracking me up!

    • Hi, Eboni! Thanks for reading and commenting.

      Yes, Mullally is a very funny, one-of-a–kind performer! I had the pleasure of seeing her on Broadway about ten years ago in YOUNG FRANKENSTEIN.

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