“What’s This? What’s Happening? What’s Going On?” – Sarah’s Top 20 Episodes of Will & Grace, Part One

Posted by Sarah

Will & Grace was never just a TV show to me, and it’s impossible to put into words how much it has meant to me over the years. It was my first positive exposure to gay representation. (I was born and raised in the suburban part of Amish Country, Pennsylvania…seeing that was a big deal.) It gave me something to laugh about during some of the worst times of my life. It was my first taste of fandom life, and that fandom was the first time I felt like I found my tribe. I made friends that became like family (in fact, two of my friends who met and fell in love because of the fandom eloped in Central Park this past March, and I was honored to be their witness), all because of four friends living and loving in Manhattan every Must-See Thursday night. The fact that the show was ridiculously funny is just a bonus. So when it ended in 2006, I was heartbroken but so thankful for everything it had given me. Since the series finale, I’ve followed the main cast pretty much wherever they went, from miniseries to stints hosting daytime TV to Broadway plays and, oh, Eric McCormack’s in a sci-fi thing now? Let’s watch all of that (it’s really great, by the way)! I always love it when there’s a mini reunion on one of their projects, but I never expected all four of them to be back on-screen together again.

But then, in September, the photos started appearing. The cast had taken to Twitter and Instagram to post pictures of what at first seemed like an innocuous little get-together. But as the get-together went on, the setting looked…oddly familiar. Like apartment 9C, Jack McFarland’s going to burst in any minute familiar. After letting me spiral into “WHAT DOES IT ALL MEAN?!” territory for a few days, “Vote Honey” was bestowed unto us, that glorious ten-minute reunion that could. It quickly went viral, leading to constant buzz about a potential Will & Grace revival. And between Megan Mullally and Leslie Jordan getting my hopes WAY up, and Debra Messing and Eric McCormack warning everyone to slow their rolls, I was almost resigned to staying in “ARE THEY COMING BACK OR NOT?!” territory for the foreseeable future. That is, until NBC’s big announcement in January.

THEY’RE COMING BACK FOR REAL, YOU GUYS.

Ten new episodes of Will & Grace are coming our way next season! And while the smallest part of me is a little nervous about it—there IS a way to get around that last episode, right?—as Rosario said when Jack caught her in bed with Karen’s gardener, “The heart wants what it wants.” And my heart wants more. So now that we’re getting a ninth season (I can’t believe I get to say that), I thought it would be fun to take a trip back to Riverside Drive and look back on some of my all-time favorite episodes of the first eight years. I’ve compiled my top 20 (pared down from an original list of 70 episodes…why is this show so good?) to share with you, the episodes that I think highlight the brilliance of this series. Some are no-brainers, and some might surprise you. Some are hilarious throughout, and some of them get very real. But combined, this showcases some of the series’ best jokes, the true depth of each character, and an amazing ability to tell a story.

This is Will & Grace as I know and love it.

20.) Forbidden Fruit (8 x 12)

My only rule going into this was that the A-story and the B-story of any given episode had to be consistent in quality in order to be considered for top 20. Well…I already broke my rule with this one. Which is not to say that Will and Grace’s story isn’t good; in fact, I find it pretty entertaining. Inspired by Will working for the Coalition for Justice, Grace decides to volunteer to design a retirement home. That is, until Will’s old boss Margot (hi, Lily Tomlin!) offers her an unlimited budget to redesign the law firm. She secretly begins work for Margot so as not to look bad to Will, completely unaware that Will quit the Coalition in favor of his old job. It leads to some good laughs as they try to keep their secrets while Margot conspires to make them find each other out, and Lily Tomlin kills every line she has with that hilarious deadpan (“Hector, I’ve only got five minutes before I have to get back to the office. I want what I had yesterday. I don’t remember what it was, and you weren’t working, but I want it anyway.”). But this is not why we’re here.

Cards on the table: if an episode gives me a moment where Karen shows emotional depth, it automatically becomes one of my favorites. It’s part of the reason she’s my favorite character on the show; 95% of the time she’s over the top, doesn’t fully know what boundaries are, and her past is so vague that it’s actually fun to count the ways that her crazy personal stories contradict each other. But it’s that other five percent that shows you that she’s human, that things affect her, that despite her assertions to the contrary, she can feel. Let me just warn you now, this is going to come up a lot during this list, to the point where I kind of want to keep a tally throughout, just to see how invested I am in the sad parts of comedy. And by “kind of want to,” I mean I’m totally doing it, so without further ado…

Karen Walker Feels Things! Tally: 1

The story starts out fun enough; Jack is under the weather, prompting Karen to invite him to stay at the manse so she can take care of him. While I would have watched the crap out of a run-of-the-mill Jack/Karen slumber party (you know you would have, too), it takes a turn when Jack keeps prodding Karen to let him inside what she deems “The forbidden room.” He even tries to get Rosario to spill the goods, to no avail. A few moments of great physical comedy and a broken forbidden doorknob later, Jack stumbles into a fully furnished nursery, where things get incredibly real. This episode breaks you in doses during its third act. It starts with the reveal of the nursery itself, because if you know the show inside and out, you remember the false alarm during season one’s “The Unsinkable Mommy Adler.” Then Karen talks about the thought of her child playing with her makeup, and you start to feel your heart ache. And somewhere in the middle of her lamentations that she wouldn’t be a good mother even though she’s gone all maternal on Jack, it hits you: that false alarm was seven years ago. She’s had this room for SEVEN YEARS, never going inside, never getting rid of what might have been, never fully getting over it. You got a sense of her disappointment during “The Unsinkable Mommy Adler,” but it wasn’t explored much until this episode, and even then, you can see her trying to save face with Jack in the room. She thanks him for allowing her to let go, gives him a smile as he says that she should keep the room for a little while longer. It’s almost as if everything is going to go back to normal…until she takes one last look at the room in a moment that has been etched in my mind ever since it first aired.

There goes Megan Mullally, shattering the hell out of my heart.

Best line:

Jack: Wow. So dramatic. The forbidden room. Reminds me of my nickname at camp: Forbidden Fruit. Unless I was in a sleeping bag. Then it was Fruit Roll-Up.

19.) Dolls and Dolls (5 x 21)

What would Valley of the Dolls look like if it was set in 2003, only lasted three days, and had very minimal stakes? It would look like Will tripping over his clogs, spraining his ankle, and being prescribed painkillers to help him heal. It’s like if Neely O’Hara had zero competitive edge and neutral opinions on The King of Queens. A big part of the reason this episode made the list is because I find high Will so ridiculously entertaining. He’s the most chill he’s ever been, not letting anything phase him. He calls off work, spending his day in pajamas catching up on American Idol (I love his Paula Abdul comments; tell me Forever Your Girl isn’t a gem of an album, I dare you. You can’t). But when he suddenly needs a refill after only a couple of days, Grace knows she and Jack have to intervene. And the intervention is fantastic; I love that the thing that FINALLY gets through to Will is the realization that he called his mother back when he said he would. Maybe on a scale of one to Valley of the Dolls, it falls on the low end, but unless you wanted to turn this show into a melodrama, that’s where it had to be. Although, part of me is kind of curious to know what Will’s alley breakdown moment would have been.

Meanwhile, Karen decides she’s missing out on real life, and tries to fix that by getting a roommate (can we talk about the fact that Madonna is the one that’s supposed to show Karen how the middle-class lives? MADONNA). The over-the-top exaggerations on the knowledge Karen lacks work because she’s always been an over-the-top character. So of course she doesn’t know what a laundromat is, or how a soda can works. Of course she marvels at running errands and doesn’t know what the hell to do with a chore wheel. And for a little while, Karen and Liz bond over their independence (because, as we all know, “Guys just mess everything up…or get murdered”). It’s nuts how quickly the honeymoon phase ends, though; once they get into a pretty intense fight at the bar, Liz is all too ready to dump Karen as a roommate. When you think about it, this works perfectly with the storyline; Karen was simply looking for the experiences most people have, and having at least one shitty roommate story is basically a rite of passage (ask me about the roommate I had in the summer of 2014 sometime…I still rage about that one). Karen’s shitty roommate story, however, comes with some sweet, sweet vengeance; once she realizes she owns the building, she evicts Liz. “Dolls and Dolls” was great as a one-time story for Karen. It gets her outside of her comfort zone for the perfect amount of time before she ultimately pulls rank in the most glorious way.

Sometimes it helps to be the over-the-top one.

Best line:

Will: Look! TiVo saved all the American Idols for me. I love Paula Abdul. And I love that we live in a world that would give a Paula Abdul a second chance.

18.) Will on Ice (1 x 11)

I don’t know why Will’s birthday makes for a great jumping off point for an episode, but it really does (it happens in another episode coming up…I’ll let you guess which one). Up until now, he’s had bad luck with birthdays, relaying a story about how he desperately wanted a cowboy party when he turned eight, only to have his mom throw him a clown party. Grace is determined to give him a birthday celebration he can look back on with joy. But come on, you guys, you know it’s not going to go smoothly.

See, Jack and Grace don’t get along the way Will hopes, so bringing everyone together for a birthday dinner is a situation in and of itself. Never fear, though! During a rousing game of “Love Her/Hate Him,” they have the best bonding moment over ice skating. Which is all fine and good, until their bonding leads to Champions on Ice the same night as Will’s birthday dinner. I love Will for agreeing to go to this thing when clearly he would rather be anywhere else, but sacrificing your birthday just plain sucks (Karen’s less than thrilled about the Champions on Ice detour as well; the moment she shouts “SKATE FASTER, WE HAVE RESERVATIONS!” is one of the moments you know she’s a queen). But his loss is our gain, because Jack and Grace have some of the best interactions in this episode that they will ever have in the series. I don’t know much about ice skating, but the giddy way they rave about it is so relatable for anyone who has ever loved something with all their heart and found someone who loves it just as much as they do; these two are basically embodying fandom life here. It’s insanely delightful, even if Will and Karen don’t get it, and it builds a stronger connection between the two that the series can play off of in later seasons. Jack going home with Rudy Galindo is just the icing on the cake.

Editor’s Note: For the record, it’s huge that Rudy Galindo made this appearance, especially since a) it happened in the first season, before the show could be confirmed as a mainstream hit and b) it’s heavily suggested that he’s going to go have sex with Jack. Galindo was the first openly gay U.S. figure skating champion and has discussed how being out affected the way the US Figure Skating Association treated him. Ironically, the USFSA does NOT have a reputation for being very accepting (just ask Johnny Weir!), so Galindo’s insistence on living and speaking his truth is not to be taken lightly. -Sage, a former figure skater who also loves this episode. 

Speaking of cake: of course, Grace wants to make sure Will gets at least one thing he wants on his birthday. Once they come home, she pulls the long-coveted cowboy cake out of the fridge—”Happy birthday, partner”—to end the night on a high note. This is the kind of thing that makes Will and Grace’s relationship so wonderful, and so easy to get on board with. All either of them wants to do is make the other happy; it’s why Champions on Ice happened, and it’s why there’s a sheet cake with plastic cowboys stuck in it sitting on their dining room table. It’s a moment of pure love and friendship that makes your heart swell when you witness it. And isn’t that what this show is all about?

Best line:

Grace: Oh my god! The best! Surya Bonaly!
Will: Who?
Grace and Jack: Surya Bonaly!
Jack: She’s French.
Grace: She’s powerful.
Jack: She’s black.
Grace: She wears blue eyeshadow and does illegal backflips.
Jack: She scares me…I crave her.

17.) Von Trapped (8 x 10)

Even with all those references to The Sound of Music sing-a-long peppered throughout the series, I really wasn’t expecting them to make an episode out of it. But at the last minute, they came through, and it was everything I ever needed. Because you couldn’t simply have the gang go to this thing; the events had to emulate the plot of the movie in its own way. Grace, dressed as Maria, suddenly becomes the childcare service of the theater, watching over seven kids. (I love when Will finally makes it to the theater: “Wow. I didn’t realize your costume was going to be this elaborate.”) Karen’s the one to set off the events causing the theater to go on a manhunt for the group by throwing a flask off the balcony and hitting someone below. (Classic Karen, right?) Jack falls for Ralph, the concessions guy who ends up ratting them out to the theater. (He’s even wearing an armband with his uniform. Good job, wardrobe department!) Rosario, dressed as a nun, is the one to stow them away in the utility closet. The whole episode is so detailed and SO fulfilling if you know the movie. The dialogue plays off of movie references so often, but it never sounds forced; and while jokes are being made, it’s always in good spirit. It really is a loving tribute to The Sound of Music.

This episode is also extremely rude for introducing James (hi, Taye Diggs!) into the picture. Look, I love that Will ended up with Vince, because their dynamic was always so delightful to me. But I completely fell for the star-crossed lover storyline that started with “Von Trapped,” and I wanted it to work so much. They had chemistry that made for excellent TV. The fact that James wants to get to know Will despite his costume that is unsuitable for the 7:40 showing of Memoirs of a Geisha endeared me to him right away. And when he raced over to the other theater when his movie was done so he could see Will again? COME ON. It’s such a wonderful gesture, and it’s frustrating when they JUST miss each other. I was so happy when he popped up again in “I Love L. Gay,” because this episode made me root for them from the start. But savor these moments now, because in a few episodes, James becomes an upsetting dick who I’m pretty sure is part of the reason we can’t have nice things.

Best line:

Grace (trying to comfort the children): Everyone gather around. You know what I do when I feel scared?
Jack: Fart a little and then deny it?
Grace: NO…Well, after that…

16.) Jingle Balls (4 x 11)

Something that you’ll learn fairly quickly throughout the course of this list: I adore the Will & Grace holiday episodes. Christmas, Thanksgiving, Halloween (“Boo! Humbug” JUST missed making my top 20, and I’m sad that I couldn’t include it, but whatever, ruthlessness), throw a holiday at these writers and they will take it and run with it. “Jingle Balls” is an excellent example of that.

Will’s story isn’t all that Christmas-y, but it makes for some amazing moments. Keeping his relationship with Robert a secret from Grace is clearly a result of his own insecurities about it. Robert’s incredibly whimsical and doesn’t really seem like the type of guy Will would be into, and if Grace is kept in the dark, he doesn’t have to face it. Sitcom 101, though: anything that can go wrong will go wrong with hilarious results. Grace invites Robert over for dinner and takes a shine to him immediately, leaving Will no other choice but to create problems where there aren’t any; the “Oh, you’re a dancer” vs. “Oh, you’re a dancer” bit is such a great move on everybody’s part. And I WISH we could see more of Robert and Will’s special dance, because even from the few jumps we get, you know it’s epic. Finally, Will confronts his own reservations with the relationship after watching Robert subsequently dance and fall on the sidewalk in an attempt to catch some snowflakes on his tongue (off camera, much to my dismay). The comedy in this one is just so rich.

Then there’s the Barney’s Christmas window debacle, aka the thing that makes this required viewing for me every holiday season. Jack’s boss, Dorleen (hi, Parker Posey!), needs a last-minute designer, but instead of recommending Grace—who is literally RIGHT THERE—he volunteers himself. And I don’t know about you, but I could definitely get on board with the Santa’s Ho-Ho-HO theme (the handle Karen has on that whip, though…); it’s amazing how thought out that whole idea is, while at the same time completely missing the mark. When Jack realizes he could lose his job if he doesn’t get this right, he gets legitimately scared for his future. But Grace, overhearing Jack’s worries, swoops in to save the day with a darkly gorgeous window she lets Jack take the credit for. Sean Hayes absolutely crushes it in this episode, first with his prayer to Santa, and later at the window reveal. Jack lighting a candle and praying to St. Nick as a last resort is the kind of thing that could never have worked with any other character, yet with him, it doesn’t seem so crazy. And that wide-eyed childlike wonder that comes with the belief in Santa when he sees a beautifully decorated window he’s not responsible for? Flawless. Grace going along with it all doesn’t hurt, either; when Jack’s on the verge of tears asking for any other explanation, her smile and her “Must be Santa” make for such a beautiful moment between them.

But perhaps the most important thing of all: this is the episode in which Karen gave me the holiday greeting I plaster all over social media every Christmas, like clockwork:

Best line:

Jack: Santa? It’s Jackie. First of all, I just wanna say I’m sorry about the time when I was eleven and told Timmy Woods that you didn’t exist. I was just trying to make him cry so I could hug him. But now I really need your help. This Barney’s window, it’s a disaster. I guess I deserve it for screwing my friend over. But I’m really scared I’m gonna lose my job. So, Santa, if you help me, I promise I’ll never ask for anything ever, ever, ever again, ever. Amen. Love, Jack. P.S., um…I know I just said that thing about never asking for anything ever, ever again, but, um, if you’re feeling generous…I would like some leather pants, um…hair extensions, and the ability to fly.

15.) An Old-Fashioned Piano Party (3 x 18)

The origin of the golden rule! No, not THAT one; I mean the one where all you have to do is put “Old-fashioned” in front of something, and you automatically have a party (remember the good old-fashioned folding party in “Dolls and Dolls?”).

This episode beautifully handles the all-too-real fear of drifting apart from your best friend, something that I think lingers in a lot of people, even if it’s in the far back of your mind. I met my best friend when I was eight years old, and while friends come and go so often while you’re growing up, she and I somehow made it through grade school, my moving to a different state, and her marriage to a wonderful guy without sacrificing even the slightest bit of our bond. But that doesn’t mean that I never worried about how our friendship might change when life steered us in different directions. So I completely understand Grace’s mindset throughout the episode, frantically making this grand purchase of a piano with both their money so they at least had something to hold them together in lieu of kids or something else of that nature. And when she still feels like Will is slipping away, Grace springs the titular party on him, complete with friends…and Mr. Zamir (PETITION FOR MR. ZAMIR TO APPEAR IN THE REVIVAL, LET’S MAKE IT HAPPEN). It’s such a weird group of people to end up with, but that weirdness works so well; I could watch Larry’s “I’m laughing because I’m uncomfortable and I don’t know why” bit on a loop forever. My favorite part of all of this, though, happens once the party is ruined. Grace spills her fears to Will, and when he starts to understand where she’s coming from, he serenades her with “Love Will Keep Us Together.” Despite Grace trying to get him to stop, he keeps singing to let her know that he’s not going anywhere, and I’m not crying, you are.

“An Old-Fashioned Piano Party” is great at further cementing Will and Grace’s relationship, but if I’m being honest, I could watch an episode that’s just the “Jack’s an erotic novelist now” storyline, for his writing (“There was Giovanni, looming large…at least from the side view,”) and for Karen’s insatiable appetite for his stories (that whole exchange where Grace is trying to have a conversation, and Karen’s only reacting to the pages she’s reading is GENIUS). I just love that THIS is the way Jack copes with the pain of a breakup, but it’s somehow in no way surprising. And Karen completely giving herself over to Jack’s writing banks on the whole no boundaries thing in such a glorious way, from barging into his apartment to demand he keep writing (“Honey, your words are rockin’ my world and my pants”) to bribing his boyfriend to break up with him again just so she can get more pages. It’s the perfect levity against Grace’s fears.

Best line:

Jack: I don’t need to write anymore. Rocco and I are back together.
Karen: No, Jack, I need these pages. I’m gettin’ so many images from this stuff, sex with Stan has gone from “I’ve got a headache” to “I’ve got to have it!”
Jack: Sorry, Kar, no can do.
Karen: But, honey, I’ve got to know what happens next. I’m addicted to these stories. Which is odd, because I don’t have an addictive personality.
Jack: Hey, even if I wanted to write something, I couldn’t, ‘cause I’m happy now. Pain was the coal that fueled the choo-choo of my art.

14.) The Hospital Show (2 x 17)

Karen Walker Feels Things! Tally: 2

It’s crazy how this show can take a pretty disgusting act and turn it into something hilarious and heartbreaking all at once. When Stan lands in the hospital with acute angina, the gang rallies around Karen; once they realize they could be there for a while, however, they start taking bets on which one of them Karen will come crying to first. Because, as Will reasons, “It’s either this or fifteen hours of reading Highlights magazine. I mean, really, how many times can you find a toaster in a tree?” They have some reservations at first—Jack asks if they’re being gross, and YES, YES YOU ARE—but ultimately become invested. You know they would never do this with anyone else in their group; perhaps the way Karen presents herself to people makes them think it’s okay to do something like this. But what I love is that Stan’s doctor—after telling Karen that he’ll be okay—rats them out the first chance he gets, and then helps Karen plot revenge. Sure, there’s a building full of sick people here, but let’s definitely make time to smoke these people at their own game. And let’s be real, they mastered this game.

If you read my post on the Brady Bunch movies, you know how much I adored Jennifer Elise Cox’s take on Jan. “The Hospital Show” is just more proof of her crazy amazing acting, because Nurse Trainee Pittman is, without a doubt, my favorite one-off character from Will & Grace, and the PERFECT person to help Karen get back at Grace. I mean, her biggest fear is needles, so why not get the nurse trainee with latex gloves falling off her fingers who’s only ever drawn blood from oranges? But the fun doesn’t stop there! During the course of the episode, Karen also manages to get Rosario to clean the hospital, make Jack cut up the credit cards she’s given him, and push Will and his annoying date together, before she reveals that she knew about their bet all along. The woman’s an evil genius.

But she’s an evil genius who refuses to let them see her sweat, as long as she can help it. The second she has a moment alone with Stan’s personal effects, she allows herself to finally break down with Stan’s wedding band in her hands. And when Grace walks in on her, meaning to apologize, it leads to a beautifully real moment for the two of them. Despite all of Karen’s jokes about marrying Stan for his money, this moment proves, without a doubt, just how much she loves him. And Grace’s support during all of this shows how far they’ve come in friendship in such a short amount of time. This being a sitcom, of course, the weight of the situation is lifted in no time; if you’re not on board with Karen by the time “Maybe I’ll give him a little booby later” happens, I don’t know what to do with you. But “The Hospital Show” is one of those episodes that shows you how beautifully this series can run the gamut of emotions, all in thirty minutes.

Best line:

Dr. Osher: Okay, Ms. Adler. This is Nurse Trainee Pittman. She’ll be taking your blood.
Nurse Trainee Pittman: I like your hair.
Grace: Whoa—whoa, her? Isn’t…isn’t there someone else who’s a little more…experienced? Someone who didn’t drive in on a big wheel?
Nurse Trainee Pittman: Oh, I don’t drive. I keep taking the test over and over again, but I’m all, “This is hard!”

13.) Secrets and Lays (1 x 17)

This show shines when it devotes episodes to the gang coming together to support one of their own in a time of need (and I guess you could lump “The Hospital Show” in there, but considering everyone’s actions, does it really count?). Stick them all together in Karen’s cabin in the woods, and it’s even better. “Secrets and Lays” is filled with the best random conversations and situations, from who they would eat first if they got stranded—Grace is too chewy?—to Jack and Karen’s misguided game of strip poker (“We just keep playing until we’re both naked!”). And Karen’s cooking skills here are so much like mine, it hurts; I don’t think I’ve ever seen meat look so beige before, but I’m sure it’s only because I’ve never tried to cook meat like that. While the stuff that springs from trying to figure out what to do in such a deserted area is fantastic, let’s not forget why they’re there in the first place: to help Will through what would have been his anniversary with Michael.

This is one of the first times we actually see Will address the heartbreak from his fallen relationship, although it doesn’t happen until the end of the episode. We’ve known since the pilot that he had just gotten out of a seven-year relationship, but he doesn’t really show how it’s affected him until the last few minutes of “Secrets and Lays.” He insists that he’s fine once he realizes the motivation behind this little getaway, but Grace knows better. It’s why she feels guilty for reuniting with an old boyfriend, why she keeps sneaking around behind Will’s back, and why she ultimately shoves Campbell the Mansicle out into the cold when Will comes home early. The interaction that follows reveals how Will hasn’t been able to move past it yet, how he still misses Michael, and that inability to turn it off as soon as the relationship ends is so relatable. By the time they’re back in Manhattan, and Will finds the scarf Michael gave him between the couch cushions, he seems to finally be processing everything. It’s a moment that has this mix of sadness and hope; you know it’s hurting him, but you also know he’ll get through it with the support of his best friends.

The ending also made me obsessed with that Third Eye Blind song for a solid few months after I first saw it, so there’s that.

Best line:

Will: Jack, that’s not a word.
Jack: Uh, yeah it is.
Will: Use it in a sentence.
Jack: Every morning, I…spramp my face with cold water. (Splashing gesture with his hands)
Will: Spramp your face? What the hell is that?
Jack: Yeah, spramp. Spramp! The bubbles from a Jacuzzi spramp up. Note how the sea spramps off the jagged rocks.
Will: Just because you do this (splashing gesture) doesn’t make it a word.
Karen: I don’t know, Will. Before I go to bed, I like to spramp on a little gardenia for Stan.

12.) Homo for the Holidays (2 x 7)

This is the part where I complain about how we never see more of Judith McFarland after this, because Veronica Cartwright absolutely slayed this role. Jack’s mom only appears in one episode, but she shows up in a pretty amazing one. Megan Mullally once said that part of the reason Will & Grace worked was because Will and Jack had been out for years by the time the series starts, making it easier for a wide audience to connect. But that doesn’t mean they can’t throw in a quick coming out anyway. It’s surprising that Jack’s the one who hasn’t yet come out to his mother, and I think that’s what makes this episode work so well; to see someone so proud of who he is freaking out over the prospect of telling the truth to the woman who raised him is the best way this series could have shown the importance and the impact of coming out. Will tries to help the process along with the new Thanksgiving tradition of telling a secret in addition to what they’re thankful for, but Jack can’t take it and retreats to the terrace, where Will drops all pretenses to comfort him with the story of how they first met:

Will: You came up to me. We didn’t know each other that well. You pulled me aside and said, “Aren’t you tired yet?” And I was tired. Tired of actually reading Playboy for the articles. Tired of keeping my Bette Midler albums in Led Zeppelin sleeves. So you took me to clubs and introduced me to people, made me realize what I was missing by not being myself. And I’m thankful for that.
Jack: I also taught you how to dance without pointing all the time.
Will: And I’m thankful for that. Now here’s my secret: I admire you, Jack. Because you are more yourself than anyone I have ever known.
Jack: Will, look, I appreciate what you’re trying to do, but this is different. My mother will fall apart. She’s…
Will: Jack, Jack, Jack, Jack, Jack…aren’t you tired yet?

Excuse me, I think there’s something in my eye.

Not all of it is so heavy, though. Karen is so genuinely pissed off that Grace is Jack’s fake ex-girlfriend that it doesn’t even matter that they only met the previous year. And Karen and Grace doubling down on Jack’s lie is amazing (“My secret is…Jack and I were doing the dirty-dirty while you two were still together!”). They go into it so hard that it turns into a legitimate fight over this non-existent love triangle. Karen’s bibb lettuce retort is such an oddly specific burn, I love it so much. And Grace knows how to dish it out too, with allusions to Harold and Maude. Deep down, what makes this work is the underlying support of the group, and the desire to not spill Jack’s secret until he’s ready to tell his mother. Once the truth comes out, though, Karen can’t help but get one final jab in at Grace: “So, Jack’s gay, huh? Hmmm…no wonder he went back to you.” It’s such a well-choreographed back and forth between the two women, and it adds so much to the episode.

Of course, this story wouldn’t be complete without Judith’s bombshell secret: the man Jack thinks is his dad is really his stepdad, and the question of who his real father is is still up in the air, setting the show up for a great storyline in the next season. This show really knew how to celebrate the holidays, didn’t it?

Best line:

Karen: You told your mother that Grace was your girlfriend! How could you?
Jack: Karen, I didn’t even know you when I made up that lie.
Karen: Oh yeah? Well, when you met me, then you should’ve broken up with her and hooked up with me!
Jack: You’re married. I’m gay.
Karen: NOT IN THE LIE.

11.) A Chorus Lie (4 x 15)

Karen Walker Feels Things! Tally: 3

I love when this show goes for stories with the unconventional pairings. Seeing Will and Grace in one storyline and Jack and Karen in another is always fun; that’s why it’s the default. But when you get to one of these Will/Karen, Grace/Jack episodes, it’s magic. When Jack tries to get in to the Gay Men’s Chorus, Owen is the only one standing in his way (hi, Matt Damon!). And when he realizes that Owen’s straight, Jack invites him over for practice, to try to trip him up. Once he realizes he’s getting nowhere—by the way, anyone notice how Owen’s fake boyfriend is named Ben?—he decides to employ his secret weapon: Grace (or, as she puts it, “…So you want me to in him for you?”) This entire storyline is peak Will & Grace from the deliciously woven-in pop culture references—the whole Divas Live back and forth between Jack and Owen is brilliant, fight me on that—to the rapid-fire dialog to the amazing physical comedy when Grace is sent in to seduce Owen. And Matt Damon goes all in here. I remember hearing about some of the big-name guest stars and being a little wary about how well they would do. But he crushed it to the point where you know that it was a one-off character, but you want him to come back so bad.

The A-story is great, but the B-story gives me one of those few and far between, but wonderfully genuine, Will and Karen moments. I know that their relationship seems like one built on animosity, but every once in a while, we get stories like this, proving that the jabs and the insults are really only surface level. Will reluctantly agrees to accompany Karen to a Valentine’s Day party on Shelter Island—after she tells him that she asked pretty much every other guy she knew—so she doesn’t have to go alone now that Stan’s in prison. And since Karen doesn’t want it to look like she’s cheating on her husband, she plays Will off as a male escort. The constant innuendos as Will is left in the dark are so amazing that the whole setup doesn’t get old, and his clueless interactions with the other women of the party as he sets up meetings with potential clients are priceless:

Will (On the phone): One o’clock? Yeah, I am booked. But you and Mrs. Sanwald are friends, right? Well, would you mind if I just did you two together? Great. Okay. …I’m scared and excited too.

Once Karen fills him in on what’s happening—“No, silly, I told everybody you were a whore, and I just want to make sure it sounds like we’re having sex in here.”—he decides to bail, but not before Karen’s reveal that he’s the only person she asked to accompany her. Her reasoning—“Because ever since Stanley went to prison, you’re the only man in my life I can count on”—is this sneak attack of emotion. She presents herself as someone who needs no one, but everyone needs at least one person they can trust wholeheartedly. And just like we saw in “The Hospital Show,” when the threat of losing that person in whatever capacity arises, she shows her true colors. Of course, Will is too good of a person to leave her in the lurch, showing up at the eleventh hour for the spotlight dance. It’s such a beautiful moment, and such a strong story for a pairing that strays outside of the Will/Grace, Jack/Karen norm.

Best line:

Karen: I’m all by myself, okay? Everybody happy? Karen Walker is all alone.
(Will enters)
Will: Oh, no she’s not. She’s got a drink in both hands, probably one in her purse, and she’s got me. May I have this dance? (Leads Karen to the dance floor)
Karen: Thanks, honey. Why’d you come back?
Will: Who else are you gonna count on?

That’s 20-11 for you! Check back soon for my top ten episodes of Will & Grace. Until then, stop for a cappuccino at Jacques and let me know how you feel about my picks thus far in the comments!