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

Posted by Sarah

We made it to the halfway point! Well…unless you’re just tuning in, in which case you can find episodes 20-11 here.

Going through the episodes I selected—but now also just watching whatever episode comes to mind, because I like staying in the thick of it, thank you very much—it’s amazing to me to see how many brilliant moments Will & Grace gave us that have stayed with me all these years…and it’s only slightly because my DVDs have been in heavy rotation since the show ended. The second I see Patti LuPone in anything now, I hear Jack shouting “SHUT UP, PATTI LUPONE!” in my head. I can’t hear mention of Antiques Roadshow without thinking of Grace doing the face (you know which one I’m talking about). And if you think “Midnight Train to Georgia” hasn’t been permanently altered for me, you are sadly mistaken. Between its massive guest stars and jokes coming from every direction, this show had its finger on the pulse of pop culture for eight seasons; I remember reading about how they stuck a Britney Spears Federline joke into “The Newlydreads” at the last minute, two weeks before that wedding happened, banking on the assumption that the marriage would last at least until the episode aired. I think part of the reason I had 70 episodes in my preliminary list—aside from the fact that those episodes are amazing—is the fact that I kept thinking about all of these moments and going “I NEED TO TALK ABOUT THIS.” And as soon as my Will & Grace loving friends found out I was doing a top 20, they chimed in with their favorite moments, some that I didn’t even think about right away but love with all my heart. Suddenly, I’m wishing I had more than twenty spots to play with…

The fact that there are SO many great moments throughout these eight seasons proves the high caliber of this show, and I have faith that the new episodes will give us more of the same. No doubt the revival will tap into the pop culture landscape—past and present—in the same way the original series did, if “Vote Honey” is anything to go by; Grace’s outrage over a butt double in Fifty Shades of Grey was incredibly satisfying because OF COURSE she would be outraged by that. But before I go into all my theories on what Will & Grace is going to look like in 2017, let’s spend some more time exploring what the show looked like back then. We’re in the home stretch now, and we’re about to encounter some truly iconic moments. Think you know what they are? There’s only one way to find out…

Let’s dive in!

10.) Marry Me a Little, Marry Me a Little More (5 x 8-9)

Confession: I was never, and still am not, fully on board with Leo. If I had my way, Grace and Nathan never would have broken up. Because even though Nathan might have pulled a dick move by going away with another woman a few days after their breakup, I’m pretty sure he never would have cheated on Grace overseas and lied about it to her best friend. But…I’m getting ahead of myself. Let’s go back to a simpler time, when the show decided to celebrate their 100th episode milestone by having Grace get married a couple of times.

 

The impulse wedding courtesy of the TODAY show (hi, Katie Couric!) is fun if only because I like imagining that duck catching Grace’s pretzel bouquet. Will, however, is less than enthused, and with good reason; to not be at your best friend’s wedding—to not even have a chance to be at your best friend’s wedding—hurts, especially as connected to each other as they are, having spent so much time contemplating Grace’s future ceremony. (Side note: during this exchange with Leo, Will tells him, “I’m never going to have a wedding of my own, and being a part of Grace’s was important to me,” and I literally clutched my chest when I watched this for notes, because look how far we’ve come in marriage equality.) But have no fear, the lavish reception is here! The gang is absolutely brilliant here, from Jack promoting the McFarland Method as he wishes Grace and Leo well, to Will’s lovely speech about how he and Grace met through fondue, to Grace singing her feelings, to Karen threatening to sic Rosario on Leo if he ever hurt Grace. It isn’t long until the newlyweds realize that after only two months of dating, they don’t really know anything about each other, like birthdays or favorite songs, or Leo’s real name (as much side eye as I give him, “People always call me Leo ‘cause my name’s Marvin” gets me every time and I’m not completely sure why?), causing Grace to freak out, leave the party, and resist Leo’s attempts to play down the situation. And when they run into Katie Couric again and find out their marriage isn’t legitimate, it seems like all hope is lost…for about two minutes. We ARE dealing with a sitcom, after all.

Which brings us to the second, meticulously planned out wedding,, and the stand-out half of the episode, mainly for the interactions between Will and Grace. Will keeps it together for as long as he can, channeling all of his emotions into making sure this whole production runs smoothly, but once Grace tells him she needs him to walk her down the aisle, he can’t keep his cool anymore. The way he initially turns her down pulls at your heart: “Look, Grace, I’ll do a lot of things for you. I’ll plan your wedding, I’ll pick the florist, I’ll even let you have input on your dress. But to actually be the one that…that hands you off to another guy…that I can’t do.” If you weren’t aware that their dynamic was about to change in a big way, Will made sure you knew it with that explanation. Eric McCormack and Debra Messing nailed it in this episode, deftly maneuvering around the weight of such a long-term relationship heading into uncertain territory. My favorite part of all of this, though, is when Grace brings him to the rooftop where they ACTUALLY first met, at a college friend’s party:

Grace: I thought you were the cutest guy I had ever seen. So I came up to you, and I asked for a drink. And you were so sweet, the way you held that funnel for me. And then I stumbled back to Nancy and I said, “That’s the man I’m going to spend the rest of my life with.”
Will: Well, we say things when we’re young. I said Human League would be bigger than the Beatles.
Grace: Will, I may be getting married today, but when I said I was going to spend the rest of my life with you, I wasn’t wrong.
Will: Well, except…
Grace: No. I wasn’t wrong. Now let’s jump.
Will: What?
Grace: Let’s keep goin’, Thelma.

That whole exchange mixed with Will secretly getting the first dance before he walks her down the aisle? This show knows how to wreck my emotions in all the right ways.

Best line:

Grace: I’m doing the right thing, right?
Will: Well…
Grace: What?!
Will: Nothing. No, I just—I’m just saying, as a friend, I want you to know that if you were thinking of calling it off, don’t worry about the people out there, and don’t worry about all those gifts. You do what your heart tells you is right.
Grace: …Are you freaking kidding me with this?!
Will: “If!” I said “If!”
Grace: The question was rhetorical, that means you’re supposed to say “yes.”
Will: That’s not what rhetorical means.
Grace: Are we talking about what rhetorical means, or about how you are freaking me out right now?
Will: Am I supposed to answer that, or is that rhetorical too?

9.) Last Ex to Brooklyn (6 x 2)

This episode could have gone so wrong in so many ways. Introducing an integral character in Will’s coming out story into the fold, who up until this point we knew nothing about other than the fact that she’s the only girl Will ever slept with (hi, Mira Sorvino!) is a risky move, especially since the last time she was mentioned was about three seasons ago. It’s even riskier to connect her to the OTHER most important man in Grace’s life. But damn, did they knock this one out of the park. Grace and Leo organize a dinner party for the rest of the gang, as well as Leo’s ex-girlfriend. Grace and Diane get on like gangbusters…until Will walks in and realizes who Leo’s ex really is. It makes sense that Grace would flip out over Diane’s connection to Will more than she would over Diane’s connection to Leo, even if Leo can’t really see that (but seriously, I have no patience for him in this episode. He’s definitely been married to Grace long enough to know her background with Will…come on, dude). As we all know from “Lows in the Mid-Eighties,” the fact that Will not only slept with Diane right after coming out to Grace, but also kept it from her for fifteen years is a huge deal. And while they generally put it behind them, I wouldn’t be surprised if Grace still hadn’t gotten completely over it by this point. So to suddenly come face to face with one of the biggest obstacles in her relationship with Will? It’s totally natural to get a little nuts, and Grace trying to keep her head above water is hilarious:

Grace: I’m not mad. And I’ll tell you why I’m mad. Because I’m not mad.
Will: You’re not making any sense.
Grace: Oh, and all of the sudden, you’re the vice president of things that make sense?!
Will: Why vice president?
Grace: Because Leo’s president, DEAL WITH IT.

The amazing thing about this episode is how they were able to take a single storyline that put a strong emphasis on Will and Grace, and still give the supporting players moments to shine. Jack and Karen are on point for the whole episode, and it helps that they have the world’s smallest dog with them to help balance everything out. I just love that Karen is hitting on Diane literally the entire time she’s there. It’s insanely direct, and so like Karen to just get to the point: “I like you…wanna make out?” (Tangent time! I always wanted to know how the show would have handled a substantial female love interest for Karen, during one of those stretches when she was either separated from Stan or under the assumption that he was dead. It wouldn’t have been outside the realm of possibility; after all, in addition to this and all the other times something like this happened, she was at one point linked to Martina Navratilova—which I’ll come back to later—and, you know, bisexuality exists. I’m just saying…) And Jack and Karen make the perfect color commentators at the dinner table when everything comes out in the open:

Finally, I’d like to submit Chompers the Earl of Puppydom for best pet name ever, please and thank you.

Best line:

Will: I made these kabobs for Grace once. She totally fell in love with the recipe.
Grace: Liar! How could I fall in love with your kabobs? I’ve never had them. Diane had your kabobs. But apparently I wasn’t good enough for your kabobs.
Leo: Wait. Why do you care that Diane’s had Will’s kabobs, but you don’t care that she’s had mine and I’ve had hers?
Jack: Silly! Diane is a girl. She doesn’t have kabobs, she has a kagina.
Karen: And nice katits.

8.) Gypsies, Tramps and Weed (3 x 7)

Surprise! I’m going to be completely predictable and talk about Cher for a minute. Because just as she is my queen diva, she’s also Jack’s queen diva. What can I say? The guy knows how to pick his icons. Once he’s in possession of a Cher doll (which he initially gave to Will as a birthday gift just so it could be returned to him, because of course), he takes it everywhere with him, speaking through it with the best worst Cher impression I have ever heard in my life, asking for an extra chair and a booster seat for it when he goes out to dinner. But it’s when the queen diva herself approaches him that really pushes this episode into the top ten. Personally, if I ever unexpectedly encountered Cher, I’d probably take the Community, Troy Barnes meets LeVar Burton route. Jack, however, decides to take the “That’s not Cher, that’s definitely a drag queen” route, and ends up challenging her to a Cher-off. I know it’s fueled by mistaken identity, but Jack’s boldness here is so rich, and his confidence that he’s the better Cher is so misguidedly epic that it leaves me doubled over laughing every time. And I love that Cher starts to leave and could simply write him off as a loon, but she’s weirdly invested now and comes back to try to convince him once more with a little “If I Could Turn Back Time.” Of course, Jack’s still completely in the dark and tries to one-up her again (and now I find myself singing “TIOOOMMMEEE” to that song more often than I care to admit), until she finally goes full-on Moonstruck on him. It’s honestly all I could have ever wanted in a Cher guest appearance…that is, until they just straight-up made her God in the next season.

Grace’s gift to Will leads him to a session with Psychic Sue (hi, Camryn Manheim!), where he originally dismisses her as being full of it. But when the stuff she tells him starts coming true, he rushes back to her to get the scoop on his love life, where she reveals to him that Jack is the one he’ll spend his life with. “Gypsies, Tramps and Weed” excels in exploring a “What if?” that I’m sure crossed a few minds at one point or another, without dwelling on it for too long; anything more than this would have been overkill and so not the point of this show. Will’s spiraling here is everything, from his freak out over Jack’s little squeezes to that glorious vision of Jack in a wedding dress holding a Cher doll bouquet. And when they finally do contemplate what a romantic relationship would be, the fact that they end up describing their current situation is the best way to end that story; their dynamic is great just the way it is.

But wait, there’s more! Just in case that wasn’t enough story for you, Grace manages to get the terrible waiter who served them at Will’s birthday dinner fired, and she feels so bad about it that she hires him as her new office assistant. As soon as she’s starting to feel good about the situation, though, she discovers that the new clients he’s been sending her way are actually there to buy weed from him (I love how the code word Lenny puts in place makes everyone seem so fixated on some random piece of furniture; “Can the four of us split an ottoman?”). The best, though, is how Karen was so against him working at Grace Adler Designs the whole time, right up until she hears why Grace fired him—“What?! Grace, I can’t believe it! I loved him!”—and runs out the door to catch him. That’s my girl.

Best line:

Jack: I feel like nesting. Let’s stay home and rent Silkwood. (Cher impression, waving the doll around) “I’m a lesbian who’s been exposed to nuclear waste, hohhhh!”

 

7.) Moveable Feast (4 x 9)

I can’t help it; I’m a sucker for a Will & Grace Thanksgiving episode. But I’m even more of a sucker for it when it crams four Thanksgivings into one. This episode is a gem right off the bat, starting with the opening phone call sequence. The back and forth between all of them is so well-choreographed, I could honestly spend this entire segment raving about it. Between hanging up on each other, putting each other on hold for a little too long, and somehow getting roped into a never-ending stream of Thanksgiving dinners? Priceless. Meanwhile, the guy Jack indefinitely put on hold manages to get into full drag by the time the gang’s Thanksgiving plans are all sorted out, and by the time you’re made to focus on his square, it’s the perfect ending (hi, Coco Peru!).

The rules are simple: everyone gets one hour at their family’s gathering. As soon as the timer goes off, they high-tail it out of there to move on to the next one, racing through the day so they can enjoy their own festivities in apartment 9C. First up: Karen visits Stan in prison, equipped with a chicken stuffed inside a turkey (that’s one way to do it…), and is blindsided by Stan telling her to sleep with other people while he’s in prison. She’s rightfully consumed with anger and confusion and “What ifs” for the rest of the episode, leading to one of my all time favorite scenes of the series…but I’ll get to that in a second. I actually debated whether or not to add this to the Karen Walker Feels Things! Tally. She’s obviously upset by her husband being okay with her hypothetical cheating, but doesn’t show it in the ways we’ve seen before on this list. Maybe this one gets half credit?

Karen Walker Feels Things! Tally: 3.5

Grace’s visit to her Aunt Honey’s place (hi, Lainie Kazan!) leads to Jack spilling the secret of her breakup with Nathan to her mom (hi, Debbie Reynolds, I miss you) and a prime Grace/Bobbi fight with Bobbi trying so hard to get the “Told Ya So” dance in, and Grace trashing her mother’s acting abilities. Jack picks up Elliot and takes the group to his stepfather’s hotel room (hi, Beau Bridges!), and for all of Jack’s warnings about what a hardass he is, he warmly opens up his temporary space to everyone and makes an effort to connect with Elliot. Which inevitably pisses Jack off because the guy was never like that when he was growing up. Then we get to Will’s mom’s celebration (hi, Blythe Danner!), filled with code words for his dad’s affair, a homophobic older brother he fights with to be the one who gets to leave early—Marilyn eventually breaks the tie and tells Will to go, leaving him confused and hurt—and an uncle whose medication makes people look like balloons to him (I love when Jack looks all wide-eyed and says, “Will, I’m a-scared,” because you hear that and think, “Yeah, that sounds about right”).

Oh yeah, and then there’s my favorite casting decision ever: the plumber (HI, NICK OFFERMAN!). I don’t need to explain to you how amazing Nick and Megan are on-screen together; we have all those Parks and Rec episodes to do that. It’s just so much fun to see a scene like this, long before Ron Swanson and Tammy 2 were even a thing. Also, just a really adorable side note: in the Will & Grace: Fabulously Uncensored book, Megan says, “It’s kind of fitting that the first time my character ever kissed a guy who wasn’t Stan, it was with the plumber—played by my husband.” Is your heart swelling yet?

All of these visits leave a bad taste in their mouths, so just before they sit down to their own holiday feast, they make the rounds one final time to make amends. Karen makes sure Stan knows she would never stray outside the marriage, Grace apologizes to her mother, Jack agrees to get to know his stepdad a little better, and Marilyn assures Will that her picking Paul to stay wasn’t a slight against him, wonderfully acknowledging the fact that Will’s friends are his family. This episode is the perfect representation of how the holidays can suck, but also how they can be salvaged.

And as if all of this wasn’t enough, while all of this is happening, Rosario is slowly devouring an entire turkey, and I love you, Shelley Morrison. I really do.

Best line:

Grace: I hope you don’t mind, Will. I had some of your water.
Will: I didn’t have a water.
(Grace looks at Jack)
Jack: Not mine.
Grace: And Karen doesn’t drink water. Oh my god! Rental car stranger water! Oh my god! How do I know this was water?! You know, when boys go on road trips, they don’t make pee stops! They just use a water bottle! Oh my god!
Will: Grace…don’t you think you would have noticed if you were drinking pee?

6.) Das Boob (2 x 3)

I would have done every single one of you a disservice if this episode wasn’t on the list. If someone casually mentions Will & Grace, I can guarantee that one of the first things you’ll think about is the Hydra Bra (by the way, how is this even a thing that was invented in the first place?). “Das Boob” is one of the best examples of this show’s crazy amazing physical comedy, all because of a misleading picture of Grace in the newspaper. That misleading picture ends up leading Grace’s high school classmate John Gregorio (or Donald Dorio, if you’re watching the syndicated rerun…why exactly was the named changed?) to pick up the phone and invite her to his art show. Once Karen points out the obvious, the two do a little boss/painfully inept office assistant bonding by shopping for some fake boobs. Karen is pure gold throughout the entire episode, from poking fun at the picture to giving Grace advice as she’s calling John (“Don’t be too chatty, just make your breasts sound big”) to her commentary mixed with Grace’s initial resistance at the lingerie store. I love that this is her way of helping the situation, because would you really expect anything different?

So Grace breaks down and buys the water bra. Problem solved, right? Not so much. Because the funny thing about stuff that’s filled with water is that when you poke something through it, it starts to spray everywhere…who knew? Hydra Bra, meet Karen’s brooch, and cue one of the most iconic bits of physical comedy on this show (possibly ever? At least in my opinion, if that counts for anything). Watching it is kind of like watching a ballet, but instead of highly technical dancing, you get a highly explosive undergarment; this show is so great at choreographing these moments. Grace isn’t going to let a little thing like a leaky bra get in the way of the moment she’s been wanting since high school, so she’s bending over backwards—quite literally—to keep her secret from John/Don, and…wait, hold up…why does he look so familiar?

HOLY SHIT, THAT’S LUKE DANES (hi, Scott Patterson!).

I admit, I was really late to the Gilmore Girls party—and by really late, I mean the original series was just released on Netflix and my friend Michael told me I should watch it because I’m a bookworm and Rory reads a lot—so I never really had the chance to put this together until a couple of years ago, and even then, I didn’t make the connection until I watched “Das Boob” for notes for this post. But this somehow makes John/Don even smarmier than I already thought he was, because now I can’t stop thinking about how it’s Luke, and what did I ever do to you except love you, early ‘00s television? And if you’re only now making the connection as well, I’d apologize, but I’m big on dragging people down with me. He really plays the skeezy douche role to perfection here, the cherry on top of this slimeball sundae being his eyes making a beeline for Karen’s cleavage the second he gets done telling Grace he didn’t call her because of her picture.

The B-story incorporates a threat to Will and Jack’s friendship when Jack discovers that Will went out with one of his exes. It’s a lighthearted fight for the most part: Jack starts stealing food from Grace instead of Will and slams the door hard to emphasize the fact that he’s pissed. And because it’s Jack, Will takes it all with a grain of salt, because he never seems to hang on to anything for more than a few minutes. But it’s the way that Jack asserts that this is a dealbreaker, the way he doesn’t slam the door the second time that proves otherwise. This is such a fun episode that I don’t think there was ever any question that Will and Jack would make amends, but Will’s “Slam the door, Jack” that makes you wonder for a moment; it’s a well-played moment. Eventually, Will lures Jack to John/Don’s art show under false pretenses (“HOW DARE YOU PLAY THE CHER CARD!”) to reunite him with the ex in question. Does that make it up to Jack? Sure…we’re in Sitcom Land, Jack’s only mad until he realizes he was thinking of a completely different guy. And all is well once again.

Best line:

John: Wait, wait, wait a second. Why are you trying to get away from me?
Grace: Okay, John, I’m going to be honest with you. We live in a deeply patriarchal society in which women are unfairly judged by…ugh. My boobies are fake. And broken.

5.) A Buncha White Chicks Sittin’ Around Talkin’ (4 x 24)

Karen Walker Feels Things! Tally:  4.5

Fasten your seatbelts, kids. It’s about to get very real very fast. This is one of those episodes that truly shows you the sheer force of this cast, and a large part of that is the formatting: with no guest stars, each character is essentially just speaking to camera—although, Will and Grace do have each other. It’s unheard of for this show, but the execution is flawless and stunning. The gang kick the episode off by listing some of the things they want to accomplish before they die. Jack wants to audition for Broadway, Karen decides to finally have a conjugal visit with Stan in prison. But it isn’t until he’s alone with Grace that he reveals what he wants: to have a baby with her. Their therapy session seriously explores the dynamic of their relationship in a way that couldn’t really be done up until this point. Taking a step like this requires some deep introspection, and this episode gives it just the right amount of gravity while still taking the form of a sitcom. It feels like a completely organic way to get from point A to point B, contemplating the reasons behind wanting to do this, not being sure if now’s the time to let go of the dreams they had for themselves. Of course, they decide to do it, setting things up for the next season and giving our titular characters a positive end to their storyline.

At least two of them get to be happy here.

My favorite thing about all of this is how the heaviest realizations are given to the characters that could so easily be written off as superficial if you didn’t know them. Karen and Jack are usually the crazy hijinks characters, so when emotion hits them, it’s incredibly impactful; it’s part of the reason “Homo for the Holidays” made the first half of this list, and it’s the whole reason I put the tally in place. Karen has some fun moments with the security camera in the conjugal visit room, and throwing slices of salami onto the bed for Stan like they were rose petals. But the mood is ruined when Stan calls to tell her he got caught doing some insider trading and got his sentence extended. I am in awe of Megan Mullally in this episode. She does so much with this scene, you can’t help but feel immensely for Karen. She’s angry, she feels betrayed, she’s sad, she’s exhausted; the way her voice gives out every now and then when she’s talking to Stan is extremely telling. And just like Karen’s last moment in “Forbidden Fruit,” the way she hangs up on Stan—“I’ll tell you something else, Mr. Walker…I’m tired, and I don’t know if I can do this anymore”—is one of those things that became etched in my mind, and I’m going to move on before this turns into a post on all the reasons why I think Megan is amazing.

Meanwhile, Jack is equally as devastating after he stumbles a few times during his audition, enough to make him stop in his tracks and step outside of the situation for a moment. The way he gradually loses the enthusiasm he once had is the perfect set up, because you can see the gears turning in his head and the light going out in his eyes, making it all the more sobering when he puts an end to his audition. Jack has dedicated so much of himself to acting, and while hearing him tell the producers that he isn’t good at this is heartbreaking, his decision to leave his aspirations behind—“I’m not an actor”—packs the biggest punch. To see someone who is usually confident enough to try his hand at so many different things suddenly feel completely defeated is hard, but this added to the depth of Jack’s character in such a beautiful way.

Best line:

Grace: Oh, this is ridiculous. We don’t sound like two people who should be having a child. This is something we should be sure of.
Will: Yeah, you’re right. I mean, it’s not like super-sizing a Happy Meal.
Grace: Yeah, ‘cause that’s always a yes.

4.) The Unsinkable Mommy Adler (1 x 13)

Karen Walker Feels Things! Tally: 5.5

The first time I ever saw Debbie Reynolds in action was as Bobbi Adler, Grace’s over-the-top mother. So when I heard the news of her death, the first thing I did was put on this episode, and I cried the whole way through, even while laughing (I just thought about the possibility of the show addressing her passing in the revival, and I am in no way prepared for that). Bobbi was SUCH a rich character comedically, but there was no way she would have worked as well if you didn’t give her the compassion she showed in this first outing. Right off the bat, you’re aware of her larger than life personality, first from her voice message, and later from her grand entrance into apartment 9C. She’s theatrical, she’s fun, she throws around crazy ideas like Will and Grace getting married. She calls Grace out on some of the most trivial things with the best intentions. But if Bobbi were comprised solely of the tiny criticisms, she would have been an overwhelmingly one-note character, and it wouldn’t have been any fun. Which is why, when Will holds onto the gardener/flower analogy in terms of Grace’s relationships, Bobbi is there to come to her defense. Which is why the beautiful “Embrace who you are” speech needed to happen to cement the foundation of Bobbi’s relationship with her daughter, and to show that underneath the nitpicking is an abundance of love for Grace, setting the stage for so many fabulous Bobbi moments throughout the series. Debbie was absolutely perfect in this role, and it’s going to be a long time before I stop wanting to cry during her episodes.

Then there’s the B-story. If you recall, I picked “Forbidden Fruit” as my number 20, mainly because of the reveal of Karen’s unused nursery. But there would be no “Forbidden Fruit” if this episode hadn’t existed. I love how they were able to make this work so well in the first season. Up until this point, Karen didn’t really have any serious moments; yes, she was thinking of leaving Stan in “William, Tell,” but as soon as the conversation she has with Will starts to shed the jokes, it cuts to another scene. By the time we get back to them, introspection time is over. So for the show to go in this direction with Karen so early into the series and go further than “William, Tell” did is fantastic. Let me turn it over to her to explain how we got here:

Karen: Well, actually, it’s kind of a funny story. A few weeks ago, it was Stan’s birthday, and I forgot to get him a present. I mean, how am I supposed to remember a thing like that? Anyway, long story short, I think I might be pregnant.
Jack: Oh, Karen, I…hope you don’t forget my birthday.

Karen doesn’t let her guard down by traditional standards, but you know she’s feeling it throughout the episode; the fact that she even told Jack at all indicates that. And by telling him, it provides an opportunity to show that as much fun as these two have together, they also have each other’s back. Jack’s making sure she’s healthy, cutting off her alcohol intake until they know for sure (no easy feat, we’re talking about Karen Walker here). When she finally takes the pregnancy test, he takes one too in the most adorable show of solidarity. And even though she’s putting on a brave face, he gets serious for a moment and wraps her in a hug to let her know she’s not alone (“Don’t hate me for doing this, but…I love you.”) At the time, it was a completely new angle to their friendship for the audience, and I think for Karen as well; the look on her face as he hugs her says it all. Ending this storyline at that honestly would have worked, but then Karen picks up the phone and asks Stan to put his kids on the line. It’s played off as a joke, but to see that just after Jack leaves her lets you in on the secret hope she had that the test would be positive. I always feel so much for her in this episode, and have felt so much for her years before “Forbidden Fruit” was a thing. Now, to watch “The Unsinkable Mommy Adler” with “Forbidden Fruit” in mind brings a whole other level to the B-story.

Karen Walker really does feel things, you guys.

Best line:

Bobbi: I know that you’ve been sitting in here ever since lunch, scared to death about turning into me.
Grace: No. I already know I’m you. What I’m scared of is what that means for my romantic life. I mean, I can’t even get a gay guy to hypothetically marry me.
Bobbi: Let me tell you something, dear. I joke about your father, but I love him. You can ask him anytime, day or night, who is the love of his life, and he’ll say, “I married her. And move over, you’re blocking the TV.”
Grace: Maybe you just got really lucky.
Bobbi: No. No, I’m not lucky. I’m terrific. And you’re terrific, Grace. Oh, honey, you are a wonderful woman. Grace, embrace who you are. (Grace & Bobbi hug as Will walks in)
Will: I’m sorry, I must be in the wrong apartment. What’s going on?
Bobbi: What’s the matter with you, Will? How could you not marry my daughter?
Will: Um…I’m gay? (spells it in sign language)
Bobbi: That’s not the point. Where else could you be lucky enough to find a girl like this? Because, gardener, flower, star, co-star, call it whatever you want to. It works for us Adler girls.

3.) The Kid Stays Out of the Picture (5 x 3)

Yes, I’m going deeper into “Will and Grace try to have a baby” territory, and yes, I know what would have happened if that actually went down. Had Grace become pregnant at this stage of the series, it would have irrevocably changed the dynamic, and I think everybody knew that…hence, no baby (at least until the last season). But make no mistake about it: this episode is a master class in acting, taught by Eric McCormack and Debra Messing. It is all about that final scene.

But how do we end up at that point? Let’s review. Will is so excited about the possibility of this baby that he’s already child-proofing the apartment and sprucing up his old cradle. It isn’t until Jack points out that he’s pressuring Grace that he offers to wait a month until the next insemination. Grace is relieved, but not for the reason he thinks; she’s been seeing Leo behind Will’s back, and wants a little more time to see where this relationship is going. There are definitely a lot of laughs leading up to the big showdown. Will and Jack singing The Carpenters is delightful as hell, and I love how the way Leo kisses Grace eventually makes its way through Karen and Jack; Karen’s reactions throughout Grace’s kiss are flawless, and Karen grabbing Jack to kiss him while Will and Grace are starting to fight is wonderfully inappropriate. When they leave and Will really starts to dive in to the fact that he knows about Leo, however, things take a brutal turn.

This fight knocks the wind out of you. Right away, you know that this argument isn’t like the ones we’ve seen them have before, but at the same time, you’re not truly prepared for the way this plays out. All the things that before were just fleeting annoyances have snowballed. None of that stuff was the breaking point back then because debating nickel pulls versus brass pulls for the cabinets wasn’t as life-altering as having a child together. But even as Will calls Grace a flake and Grace calls Will a control freak, there’s still this miniscule glimmer of hope that they can make it through this. Which then gets squashed under Will’s foot when he predicts how Grace and Leo’s relationship will turn out:

Will: Oh, let me tell you where this is going. You’ll end up hating him in three weeks because, I don’t know, he has a weird chest hair pattern, or he doesn’t like watching E! Or he’ll end up hating you because you’re too needy. Then you’ll fall apart, I’ll pick you up, and then magically, you’ll be ready to have a baby.

That’s when the argument really pierces you from all directions. If you didn’t think this fight was nasty before, it certainly is now, between Will’s assessment of Grace’s relationship and Grace firmly telling Will, “I am not gonna be miserable for you,” all culminating in Will kicking Grace out of the apartment. I remember watching this as it aired, tears streaming, and I think I knew deep down that this rift wouldn’t last; I mean, the season JUST started and show IS called Will & Grace (I’m reminded of Mr. Stein’s reasoning for his abrupt return to Doucette & Stein in “Boardroom and a Parked Place”: “If there’s no Doucette, no Stein, what’s the company gonna be called?” to which Will replies, “…’And?’”). But that final scene is so emotional, so raw, so powerful that in the moment, I was convinced that there was no coming back from it. They did in the next episode, because they had to, and I implore you to watch “Humongous Growth” if only for the scene where they make up in the bouncy castle. When Will utters that “You don’t live here anymore,” though, it feels so final, and it leaves you gutted. It has been said that this was the only take they did for this scene, and I’m just stunned that these two could take what I’m sure had to be one of the hardest scenes of the series and make it perfect on the first go.

That is how you surprise an invested audience.

Best line:

Karen: Honey, what is the problem? It was just a kiss.
Grace: Oh, no, no, no. You don’t understand. It was a REALLY good kiss.
Karen: (scoffs) Show me.
Grace: No.
Karen: Show me.
Grace: No.
Karen: Come on, we’re both stoned.
Grace: Forget it.
Karen: Shut up and show me.
(Grace grabs Karen, kisses her the way Leo kissed Grace)
Karen: Yeah, you’re screwed.

2.) Lows in the Mid-Eighties (3 x 8)

This wouldn’t be a complete top 20 list without the Will and Grace origin story. We’ve had hints of their past in the first two seasons—the first time I remember them explicitly saying they had dated was at the end of “Hey-La, Hey-La, My Ex-Boyfriend’s Back,” and that was about halfway through season two—but we never really got the details. But of course, we couldn’t be kept in the dark forever. AND it’s a Thanksgiving episode! You know how I feel about Thanksgiving episodes.

We’re taken back to a kegger in 1985, just before Grace and her gloriously bad perm, and Will and his 847 popped collars travel to Schenectady to spend Thanksgiving with Grace’s family. When Will is left alone to clean up afterwards, he literally finds Jack McFarland (Since 1969) in the closet, setting him off on a journey to self-discovery. And just like “Homo for the Holidays” did with Jack coming out to his mother, Will’s struggle between who he is and disappointing someone he loves deeply dominates the episode, and everyone involved shines here. Jack’s over-the-phone support is exactly what you would expect from him; he pulls no punches, but it’s also clear that he’s someone to depend on during a time like this. Will proposing to Grace so he wouldn’t have to have sex with her is the best kind of panicked decision to raise the stakes. And when Will finally comes out to Grace in the kitchen, the heartbreak and frustration on both ends is played so astoundingly well, to the point where, once Grace throws him out, you catch yourself wondering for a second whether or not they’ll see each other again…even though they’re definitely the ones telling this story together in 2000.

Fast forward to 1986, when Will and Jack are shopping for their Thanksgiving meal. Just after Jack races to the frozen food section to save face (remember that time he told Will he was in love with him?), Will runs into Grace for the inevitable awkward reunion. As they’re starting to ever so slightly move in the right direction, Will fatefully ducks to avoid being seen by Diane (hi, someone who is definitely not Mira Sorvino!), causing present-day Grace to want to figure out that fifteen-year-old mystery. When the truth comes out, the betrayal Grace feels is overwhelming, but this all leads to that beautiful scene in the rain. You always knew that Eric McCormack and Debra Messing’s chemistry was on point, but Grace’s anger mixed with Will trying to explain himself makes it glaringly obvious. And then the whole thing comes full circle, with present-day Will and Grace saying the same thing to each other in front of the same grocery store that they did fourteen years ago when they reunited, sending my emotions in the best tailspin.

 

Also, I would be remiss if I didn’t address how fantastic ‘80s Karen is. The over-the-top story of how she declared Stan to be the love of her life makes for a wonderful balance in this episode. She has three people lined up to marry her, including a sultan and Martina Navratilova, and it’s at this point I’m left desperately wanting another flashback episode that addresses how all of this came to be. I love how she turns them all down in such a rapid-fire way so she can be with a guy with “squat little legs and a bad case of recurring psoriasis.” There’s just one slight snag in the plan: Stan’s still married. And in the middle of venting to the bartender about it, the cigarette girl—who just happens to be Rosario—steps in to get her to snap out of it. Which, if this is the true story of how they met—and how can we ever really be sure?—it’s hilarious that out of all the insane stories Karen has spouted over the years, the most mundane one is the thing that actually happened.

But seriously…where is my Karen flashback episode?

Best line:

Grace: I can’t—I don’t even know—How long have you known this?
Will: I think on some level I’ve always known, you know? I mean, the guy toweling himself off in the Zest commercial always did a little too much for me.
Grace: Oh, great. Great! The Zest guy knew before me!

1.) Bed, Bath and Beyond (4 x 7)

Karen Walker Feels Things! Tally: 6.5

Let me tell you something: it was not even a fair fight for the top spot. This was always going to be number one. Before I even pitched the idea of a top 20 list to Kim and Sage, this was number one. If you asked me to tell you what Will & Grace was all about, I would just sit you down in front of the TV and play you “Bed, Bath and Beyond.” Because this episode IS Will & Grace to me. I know earlier I said that if I had my way, Grace and Nathan never would have broken up. But if they had to break up, I am so grateful this show gifted us this episode. Like “Secrets and Lays,” “Bed, Bath and Beyond” is one of those instances where the gang rallies around the one in distress. Like “A Buncha White Chicks Sittin’ Around Talkin’,” it’s only the main cast (I’m including Shelley Morrison in that because, come on, it’s Rosario). And in setting it up this way, it becomes the best example of all the amazing qualities that make up this show’s DNA.

Grace hasn’t been able to get out of bed for three days following her breakup with Nathan, and as Will, Jack, Karen, and Rosario try to bring her out of her sadness, they eventually confront their own insecurities.  Let’s go down the line and see how each of them try—and fail—to pull Grace out of her funk. Will attempts to win her over with vandalizing Italian fashion magazines and dressing her up to face the day. Grace is having none of that, though, and her criticism of his efforts is glorious (“Will, I look like I’ve been flattened by a steamroller.”) and I love that she doesn’t even try to push the clothes off of her before she goes back to sleep; Debra Messing is phenomenal in this episode with the choices she makes. Jack sneaks into her room when Will leaves him alone in the apartment and decides to serenade her with his latest addition to his one man show: a medley of tunes featuring the word “one” (because that’s how you set Jack 2001 apart from Jack 2000…get it?) Which would be fine if the songs didn’t all have to do with finding The One or leaving The One. The fact that he brings her to tears and spins it as a positive thing for his art is pure Jack, and I love him for it. Then there’s Karen’s attempt at roleplay to help Grace with all the unresolved issues of her relationship with Nathan. The fact that Karen’s connecting with her with something that helped her cope with Stan’s prison sentence is a heartening reaching out. Then it totally goes off the rails when Karen REALLY embodies the spirit of Nathan:

Grace: I mean, we had such an incredible connection. I mean, when in your life have you had sex like that?
Karen: Oh, uh…actually…never?
Grace; Didn’t you love having sex with me?
Karen: (Thinking about it) I did.
Grace: Wasn’t it amazing?
Karen: Yeah, it…it was, it…it WAS amazing.
Grace: I miss having sex with you.
Karen: I miss having sex with you, too.
Grace: And I miss everything else about you.
Karen: I miss everything else about you, too.
Grace: I love you, Nathan.
Karen: I love you, Grace!

 

What’s a little impromptu make out between friends?

Whether or not that was the actual thing to get her out of bed (part of me kind of wants it to be the thing?), Grace crashes the dance party in the living room, ready to come back to civilization. Until a voice message from Nathan’s travel agent asking how his new girl spells her last name sends her retreating back to the safety of her blankets. I said before that this is a dick move on Nathan’s part, and while this may be his way of coping, it’s no excuse. To find out that the one you were ready to pledge your life to is running off with someone else before you even have a chance to make it out of bed is brutal, and Grace’s instant retreat kills because it makes so much sense. When bringing out the big guns—aka Rosario—fails, partly because she has no hose (which is just…what?) and partly because she got suckered in to watching Grace’s slides, the gang decides to take matters into their own hands, literally dragging Grace out of bed and into the shower. These three are literally falling over each other and making every effort they know how to get Grace through this. But sometimes that much help is overwhelming, no matter how good the intentions are. And when Grace finally puts an end to it, she ends up helping the others to some realizations of her own.

Grace’s speech and the epiphanies that follow constitute some of the most beautiful work I have ever seen on this show and sitcoms in general. Grace points out all of the things the others have gone through to show them that she could never handle it the way they can. One by one, though, they follow her into her bedroom to shatter the walls they’ve been keeping up. Will’s admission that he hasn’t been able to be in a good relationship since Michael left hurts, because you know it’s been lingering in him since the series began. Karen’s admission of loneliness contradicts that surface appearance of needing no one but herself, and as she climbs into the bed with Will and Grace, the fact that she’s not alone in that moment means everything. And Jack…well, he’s Jack. He doesn’t so much focus on the fact that Grace called him our on his relationship habits as he does on the fact that she didn’t call him a dancer, even though he thinks that’s his strongest asset. But as he joins them in the bed, it’s this point that the episode becomes less about helping Grace through a tough time, and more about seeing each other to the light at the end of the tunnel. That flip is seamless, and so powerful. This is friendship at its finest.

When you get down to it, these characters—and this show—are filled with so much love. As Grace looks back at her sleeping friends before shutting off the projector and stepping out of the bedroom, you know she can feel it, no matter what quips they throw at each other, no matter the disagreements, no matter the crazy stunts that make for entertaining sitcoms. But we can feel it, too, not just in this episode, but throughout the entire series. Underneath all of the iconic moments, all of the sharp dialogue, all of the physical moments that leave you in stitches, there’s a strong bond between these four people that can carry them through anything. I can’t think of a better representation of that than “Bed, Bath and Beyond.” You don’t have to take my word for it, though. Just ask Grace:

Best line:

Grace: Look, I’m sorry I’m not as strong as you all are. I wish that I were, but I’m not. Will, your lover of seven years left you, and you have to live every day knowing that he’s out there loving someone else. I couldn’t do that. I would die. And Karen, your husband’s in prison, the rock of your life, and you don’t know when you’re gonna see him again. If I were you, I’d be a total wreck. And Jack, you’re so resilient. You’re a 32-year-old actor/singer who gets involved in a million different relationships and never gets invested in any of them. I wish that I could do that, but I can’t. I’m not like any of you. I just handle things differently. So, please, just let me go back to bed and deal with things the only way I know how. (Grace goes back to bed)
Will: (entering the bedroom) You know what? You’re right. I’ve deluded myself this whole time into thinking that I’m okay, but the truth is I haven’t been able to have a good relationship since Michael. Maybe you’re right to stay in bed and deal with it. I mean, maybe I’m the one who got out of bed too. (Gets into the bed)
Karen: (entering the bedroom) Honey? You were right. I don’t know when Stan’s coming back. I mean, for all I know, it could be years. I’ve got to stop lying to myself, Grace. I’m really lonely, I…I miss him. (Gets into the bed)
Jack: (entering the bedroom) When you said…I’m an actor/singer who jumps from one relationship to the other, it made me realize…you didn’t say dancer. And I’ve always felt, in my heart, that the dance is my strong point. That’s so depressing. (Gets into the bed)

Did your favorite episodes make the cut? Did I miss the mark? Let me know in the comments; there’s a good chance your favorite is one of mine too. And be sure to join me here when the revival premieres, because I’ll be recapping each episode for you! I should be able to turn my incoherent excitement into actual words by then. Maybe. We’ll see.

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4 thoughts on “What’s This? What’s Happening? What’s Going On? – Sarah’s Top 20 Episodes of Will & Grace, Part Two

  1. I can’t remember the name of the episode but I LOVED the Thanksgiving that they all share at Vince’s parents’ house. Grace and Karen fighting over what turns out to be a 16 yr old? GOLD. This is a good list. I wasn’t sure what your No.1 would be, but it is a good choice. I have every season on DVD and A Chorus Lie is one of my go-to’s. Dyeing is Easy, Comedy is Hard is also one of my faves – I believe this is the one where Rosie O’Donnell is Elliott’s mother. I love the line, “say something lesbionic!” HOME DEPOT. It doesn’t surprise me that your original list was 70 episodes long. Thanks for putting this together.

    • “Queens for a Day” and “Dyeing Is Easy, Comedy Is Hard” were definitely on my preliminary list. I love the story Megan Mullally told about “Queens for a Day” where they were filming for so long, by the time Will brings out the Thanksgiving meal, Megan just ends up saying “This scene is so long!” when everyone’s reacting to the meal, instead of what she was actually supposed to say. If you listen closely enough, you can definitely hear it. I love it so much. And Rosie O’Donnell was AMAZING in “Dyeing Is Easy, Comedy Is Hard,” and the Home Depot line is one of my favorites in this show.

  2. Lucy says:

    I wholeheartedly agree with your choices (some of the earlier seasons had GOLD episodes) but I want to share my love for a couple of gems from the later seasons. “No Sex ‘N’ The City” was an amazing episode for me bc watching Karen and Jack geek out over TV shows was SO much like looking in a mirror (especially the scene where they tried to find new shows but got bored after five seconds “Fat guy, skinny wife” LOL.) Another episode I loved was from season 7, I think it was called “Partners”, because Lily Tomlin is literally the queen of my heart and I would literally watch an entire show with Margot just insulting her employees. I really wish they would have extended her arc because she was amazing and had great chemistry with the rest of the cast.

    • “No Sex ‘N’ The City” is FANTASTIC, I love Karen and Jack’s storyline in that one, especially when they come face to face with Bebe Neuwirth. And I will plant my face in front of anything Lily Tomlin does, I think she’s so phenomenal. So I would have GLADLY taken more Margot.

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