The Ten Best WILL & GRACE Episodes of Season Six

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.

Will & Grace’s sixth season is a mixed bag. It’s got some valuable character material but is burdened by developments that limit the year’s overall quality. One major issue is the same as in Five: the marriage of Grace and Leo (Harry Connick, Jr.), which was supposed to represent positive growth for Grace, but couldn’t because his character was so ill-defined that we were never able to root for their pairing. What’s more, Connick’s Leo spent the better part of Five — and now Six — out of the country in Doctors Without Borders, giving weekly story a break, but making it impossible to develop for him a personality. Accordingly, Grace is trapped for two whole years — including this season — in a relationship that simply doesn’t work, best evidenced when, in the absence of character-driven drama, the year has to contrive for them conflict and a cliffhanger: Leo’s off-screen infidelity, which we learn about in the finale. It’s a workable tactic, but Leo’s such a non-entity that it’s hard to care; we’re no longer fully invested. Why are we no longer fully invested? Well, aside from Leo, the end of Six is a mess, thanks to the story-driven, on-location, guest-star filled finale where Karen marries Lyle (John Cleese), father of her old rival Lorraine. It’s an ostentatious bomb — Jennifer Lopez appears, but is the least of the entry’s problems (she’s actually the series’ funniest cameo-making pop diva; see next week) — because while Cleese has proven himself elsewhere, his Lyle is a situational presence with not enough definition in contrast to Karen. Thus, like Leo and Grace, this is a relationship more driven by MSTV gimmickry than anything else… But all that is a secondary concern, aiming to disguise what’s really making Six drag: the absence of Grace, for Debra Messing was pregnant and had to miss five episodes (including the year’s last four), with her usage further limited throughout the season. Though a wise decision to spare the character of the actress’ blessed event, every script that can’t use Grace as a main player is unable to acknowledge the series’ dramatic thesis and core relationship, meaning that, no matter how funny a Grace-less teleplay happens to be, it’s automatically at a weakened capacity…

So, Six is a year that essentially can’t be one of the best, given its use of Grace. Yet if Grace — and Karen — aren’t being featured well, then there’s some good news, because for the first time, the men actually have a better year than the women. Not only does Six devote more time to Jack’s career — his nurse arc doesn’t yield great episodes, but it’s a commitment to his character that pays off when he rededicates himself to performing at season’s end — both he and Will get recurring love interests for the first time in, well, a while. As Jack dates the wealthy Stuart (Dave Foley), one of his character’s few beaus to last more than a week, Will finally has his first serious boyfriend since Season Three: Vince (Bobby Cannavale), the cop. Both of the guys’ paramours have easily more definition than the women’s — simply by how they’re introduced — but more to the point, because they’re not used to prop up heavy and preordained Sweeps stunts, they don’t feel like contrived story vessels; they’re characters in their own rights, and their relationships are therefore allowed to grow in tandem with their depictions. Vince — who’ll go on to receive even more definition next year and be one of the few bright spots of the seventh season — is particularly valuable, for Will has spent three whole years without a romantic partner. His arc has basically been a failure until now, because if Will, like Grace, has been in pursuit of romantic happiness, then the series limiting this quest in episodic story, and outright denying him the chance to move forward in an incrementally positive direction, is the very definition of his character being denied growth. Now, sure, Grace maybe hasn’t evolved either — because of Leo — but at least she wasn’t sidelined like Will… To that point though, because his arc is resumed — essentially for the first time in three years (the closest we got during the interim was Barry) — Season Six does have something worthwhile to celebrate: the progression of Will’s love life, and with an interest who makes investment in their coupling possible… So, even with the lack of Grace that disqualifies a portion of the season, Six isn’t a total dud, and there’s some good stuff here — including a few wonderful episodes. That’s why, as usual, I have picked ten that I think exemplify the season’s finest.


01) Episode 124: “Last Ex To Brooklyn” (Aired: 10/02/03)

Grace throws a dinner party for Leo’s ex-girlfriend… who has a surprise connection to Will.

Written by Alex Herschlag | Directed by James Burrows

My choice for the season’s Most Valuable Episode (MVE), “Last Ex To Brooklyn” is probably the series’ most thesis-related one-off-classic since the days when such stories could be expected with regularity — Seasons Two/Three. In fact, with a plot that deals with Will and Grace’s history and derives its conflict from something made clear to us all the way back in the pilot — that Will and Grace would be a romantic couple but for the detail that he’s gay and not going to change — this installment is the most premise-affirming show since, well, probably “Lows In The Mid-Eighties.” Speaking of that show, this one takes its story from a revelation from the former’s final moments — namely that Will slept with a woman during his hiatus from Grace in order to confirm his own sexual orientation — and, ta-da, magically introduces us to said woman, a beautiful blonde played by Mira Sorvino, who, oh yes, also used to be Leo’s ex-girlfriend, too. Yet that hardly matters as much — to us or Grace — because the series not only doesn’t care very much about the ill-defined Leo, but also because the woman’s history with Will hits Grace right in the dramatic heart of her character, where that original central conflict has never really subsided. So, this one’s got a great foundation, but credit must also go to the execution, which gets all the regulars, Leo, and the special guest together at the same time and place for a dinner party that plays out like a one-act — a design that prizes character interaction, highlighting the relationships and the strength of the performances… just like classic Will & Grace. And believe me: this is classic Will & Grace. Maybe for the last time…

02) Episode 125: “Home Court Disadvantage” (Aired: 10/09/03)

Karen tells Grace that she doesn’t like Leo, while Will spends time with his mom.

Written by Jhoni Marchinko | Directed by James Burrows

Both halves of this wholly affable offering work because they’ve got character relationships motivating the action. On one side, a story about Will spending more time with his drinking and depressed mother (Blythe Danner) is nothing more than the functional start of a mini-arc in which she lives with him in his apartment, driving him crazy and impeding his love life. But it’s also a chance for two characters with a strained dynamic of their own to work out some issues — and because parent/child relationships are always great fodder for conflict and insight into specific characterizations, this is something of a welcome occurrence. Meanwhile, the rest of the outing finds Karen confessing to Grace that she doesn’t like Leo. Not even a little bit. It’s a wonderful admission — not because it affirms our perspective about him (and I do like to point out: from the start, Karen adored Nathan but disdained Leo) — but because it forces Grace to deal with a relatable scenario of what happens when a friend doesn’t like your significant other. Also, because the series has done a poor job of defining Leo and mingling him with the group, “Home Court Disadvantage” gains points by acknowledging this deficit and exploiting it for episodic story. A highly enjoyable, underrated sample of the season.

03) Episode 131: “Strangers With Candice” (Aired: 12/04/03)

Will and Grace meet odd dates, while Karen feuds with Candice Bergen.

Written by Sally Bradford | Directed by James Burrows

There are a handful of truly terrific installments here in Season Six, and, okay, none of them quite match the aforementioned MVE in being an absolute classic for the way the dramatic thesis is invoked in story, but entries like this — “Strangers With Candice” and the below “Fanilow” — are written and structured so well that they’re among the strongest from the entire latter half of Will & Grace‘s run (which complicates our view of Season Six’s inherently dissatisfying Grace-less standing, because while other years are never handicapped so severely, they’re also not really able to produce three gems or near-gems). Like “Last Ex To Brooklyn,” this one benefits from putting all the characters together at the same time and place — a restaurant — where freewheeling lunacy is then allowed to run rampant, as both Will and Grace wind up with dates and Karen pranks one of her many rivals, Candice Bergen, who appears as herself and tosses off a couple of fine zingers. The comedy of the Will/Grace material is that their dates are nonsensical — Leo is out of the country again but Grace is still married, and Will, despite his affinity for Grace, only sleeps with men, meaning the woman he picks up is nothing but a farce. Yet the smart teleplay keeps the proceedings light and airy, with a tight structure that calls everything back and doesn’t miss a beat. One of my favorites.

04) Episode 132: “Fanilow” (Aired: 12/11/03)

Will tries to meet Barry Manilow, while Grace learns that her mother is in town.

Written by Kari Lizer | Directed by James Burrows

As with the above, “Fanilow” is one of the season’s standout offerings, and part of this comes from the astute construction, which builds itself entirely around the cameo that Barry Manilow makes in the final few moments, but neither tries to hide this fact nor allows it to overtake the abundant character comedy that otherwise flows throughout the half-hour. Once again, the design is smart, for everything takes place within a finite period of time and space, as Will lines up for a Barry Manilow concert — he’s a “Fanilow,” as is the obsessed fan next to him, played by Roseanne‘s Sara Gilbert — and the other characters take turns holding his spot. They all get involved in separate adventures though; as Will schemes to be taken backstage by flirting with a tour manager to whom he’s not attracted, Karen discovers her inner “Fanilow,” and Grace sees her mother (Debbie Reynolds, of course) across the street and is jealous to discover that she’s in town to meet with Jack. The sincerest stuff here comes from mother/daughter — it’s one of the only times these two have a “real” moment — but the show’s claim to excellence is the big laughs that are plentiful in the teleplay, aided by a design that simply pivots the characters around a single idea, letting them be themselves with limited story getting in their way.

05) Episode 134: “A Gay/December Romance” (Aired: 01/22/04)

Will worries that he has a sugar daddy, while Grace boycotts a noodle shop.

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

Admittedly, all of the true classics in Six were broadcast in the fall of the season, and by this point on the list, there are only two types of outings remaining: the ones that I think are underrated and deserve more credit for how they use character, and the ones that I think are overrated because they’re too reliant on comedic Victories In Premise. I hope it’s obvious already which category “A Gay/December Romance” falls into — the latter, naturally — for there’s no way to avoid the fact that the story with Will stumbling into the role of boy toy for a wealthy older man (Barney Miller‘s Hal Linden) is but a funny idea, inverting the roles that Jack and Will usually play. And the subplot with Grace and the noodle shop that she loves and pettily has to boycott… well, isn’t that the kind of story that any high-strung New Yorker could propel? It screams of Elaine Benes, given how Seinfeld-ian and trivial the offense, but it just as easily could work with one of the Friends ladies. Thus, it’s not at all one of my favorites, and yet, because I think the year’s baseline of humor is maintained, and because I don’t have any notable replacement options, I offer it here for exactly what it is: a pair of amusing notions.

06) Episode 136: “Looking For Mr. Good Enough” (Aired: 02/19/04)

Will, Jack, and Jack’s new boyfriend take a cooking class.

Written by Gary Janetti | Directed by James Burrows

This one’s somewhere between an underrated character show and an overrated Victory In Premise for the A-story, in which Will feels like a loner at a cooking class filled with couples, including Jack and his new boyfriend Stuart (introduced in the previous entry and played by NewsRadio‘s Dave Foley), is enlivened by the gaudy inclusion of Tracey Ullman as the teacher and the plot mechanics of the man hired to come in and be Will’s partner. But not only is it successful comedically — Ullman easily gets all her laughs — it also highlights just how tragic Will’s love life has been as of late, and kind of readies him, and us, for a more significant romantic arc to come. Meanwhile, the subplot is decent as Suzanne Pleshette returns as Karen’s mom, and although I maintain that the series never uses her well, and subjugates their relationship in favor of more story-led notions, this is more memorable than her previous appearance, which introduced her via heavy narrative, because it better uses their dynamic within story (and includes Grace, which helps give it a little more shading and strength).

07) Episode 139: “East Side Story” (Aired: 03/11/04)

Will and Grace compete against a lesbian couple in apartment flipping.

Written by Gail Lerner | Directed by James Burrows

Just like “A Gay/December Romance,” I put “East Side Story” in the overrated category, mostly because I believe the bulk of its appeal comes from the A-story that features Edie Falco and Chloe Sevigny as an aggressive lesbian couple that competes with Will and Grace as apartment flippers… which, incidentally, Will and Grace have temporarily become in the past few episodes. (It’s a brief idea that doesn’t do much but provide an excuse to get them together, which is apparently harder for the series to do organically in this era, since Grace lives by herself in Brooklyn with a never-in-the-country husband.) The mechanics of the breakup scheme between the two pairs is a bit contrived and never really gets its big laughs as far as I’m concerned, but I can appreciate the risk that the story takes and agree that it jibes with Will & Grace‘s overall comedic tone. Also, I think the subplot, of Karen worrying about Stan’s reaction to her recent engagement to Lyle, makes sense for her character, and even though it traffics in broad hahas and a celebrity medium cameo, I also think it fits the series’ aesthetic.

08) Episode 140: “Courting Disaster” (Aired: 03/18/04)

Jack thinks Stuart is cheating, while Will defends Karen in traffic court.

Written by Sally Bradford | Directed by James Burrows

After three years of never having a serious love interest, the Will of Will & Grace finally meets a legitimate beau in Vince (Bobby Cannavale), a traffic cop whom Will faces off against in court after having (foolishly) agreed to attempt driving lessons with Karen… Now, I hate court centerpieces — they’re a narrative gimmick that usually demand a lot of strained credulity, both in character behavior and regular ol’ common sense — but I appreciate that the entry stops short of these shenanigans by having Vince and Will turn out to have a quasi-history, given that they’re mutual friends of Joe and Larry, who have been trying to matchmake them. This takes the dramatic energy away from the situation and puts it into a more valuable vein: the character arc… Meanwhile, the subplot has fun with Jack and Grace — Jack, like Karen, is a comedic agent who gets laughs with whomever he’s paired, but it’s especially nice to see him with Grace — by playing up Jack’s paranoia in his new relationship with Stuart, whom Jack falsely is led to believe is cheating. They don’t break up (yet), but this is Foley’s last appearance.

09) Episode 141: “No Sex ‘N’ The City” (Aired: 03/25/04)

Grace gives Will relationship advice, while Jack and Karen mourn their favorite TV shows.

Written by Steve Gabriel | Directed by James Burrows

Metatheatricality has long been a popular television device, because it telegraphs a sense of self-awareness, and therefore a perceived degree of smarts, making both show and viewer feel intelligent. I call this “a wink,” and while sometimes winks can undermine character integrity by making us doubt a show’s sincerity regarding its leads, some series — especially those that NEVER take themselves too seriously — can use a wink effectively, if employed judiciously, as a comedic tool. Will & Grace is one of those series that’s able to use a wink purely for comedy, because a) it’s been a long time since its characters were treated as anything more than likable purveyors of jokes and b) the campy nature of the humor has always enabled the use of external sources. That’s why this episode can build a Jack/Karen subplot all around the TV literate idea of the two mourning the demise of Friends, Frasier, and Sex And The City — with a Bebe Neuwirth cameo thrown in for ostentatious laugh-seeking good measure — and get away with it… Fortunately though, the Will and Grace subplot, as the former makes a fool of himself in the early days of his new relationship with Vince, provides more underrated character-furthering substance, and gives “No Sex ‘N’ The City” some internal value, too.

10) Episode 142: “Fred Astaire And Ginger Chicken” (Aired: 04/01/04)

Will introduces Grace to Vince, while Jack auditions Karen replacements.

Written by Ain Gordon | Directed by James Burrows

Probably the most underrated excursion here, “Fred Astaire And Ginger Chicken” has the distinction of being the only sitcom credit to date for playwright Ain Gordon, the author of this surprisingly character-wise, albeit slightly odd — and you can’t fully put your finger on why — offering. I suppose part of the problem is the A-story, in which Will introduces Grace to Vince for the first time and frets over the impression that she doesn’t like him; it suffers because Debra Messing’s usage is so qualified. (This would be her last appearance in Six — she doesn’t appear at all in the year’s final four half-hours.) As a result, what should be a big important story for the two main characters, one of whom hasn’t been happy in his own life for years, doesn’t quite get the dramatic attention it should. Nevertheless, it’s appreciated, as is the lighter subplot, in which Jack fears that his relationship with Karen will change once she gets remarried, so he decides to go out and audition women to be her replacement. It’s an easy comedic idea, yet it’s valuable because it reaffirms the strength of their bond, which is usually treated as trivial and jokey, but has actually grown to become pretty honest and solid in its own right.


Other episodes that merit mention include: “Me And Mr. Jones,” which guest stars James Earl Jones as one of Jack’s befuddled acting students in a silly and uneven script that gets its laughs, but only from this cameo, and “The Accidental Tsuris,” which sees the return of Minnie Driver’s Lorraine and also introduces us to Geena Davis as Grace’s sister, but sadly takes the juice out of the sibling relationship by redirecting too much of the focus onto the obviously constructed scenario. Of more Honorable Mention quality, meanwhile, are “Heart Like A Wheelchair,” which first introduces us to John Cleese’s Lyle, who never is funnier, and “Nice In White Satin,” which is notable for featuring Jack Black as Karen’s doctor.


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

“Last Ex To Brooklyn”



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

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

  1. Love Vince and agree its so nice to see Will have a real relationship and with someone who isn’t boring like Leo. I didn’t mind Lyle but those Vegas episodes are real dogs. Any episode of WILL & GRACE without Grace is only half complete.

    Also glad to see “No Sex n the City” here. It’s so meta but it’s fun!!!

    • Hi, Elaine! Thanks for reading and commenting.

      Yes, “No Sex ‘N’ The City” references an important part of the series’ identity — its status as an MSTV offering!

  2. “Last Ex To Brooklyn” is my favorite episode outside of Season 2. I wish there was more like this in the last few seasons. *Sigh*

    • Hi, Ian! Thanks for reading and commenting.

      Yes, it’s rare to see an episode of such dramatic integrity at this point in the series’ run.

  3. Thanks for another great review — gives me a whole new appreciation for “Last Ex To Brooklyn,” which somehow escaped me.

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