“Will & Grace”: The Holiday Episodes
During its iconic 11-season run, Will & Grace produced a number of classic holiday-themed episodes. In honor of the imminent holiday season and my unwavering nostalgia, I decided to rank them all.
Author’s Note: This is the fourth article in the author’s series about Will & Grace. Click here for Part One, which analyzes the revival trend and recounts my night at an episode taping. Click here for Part Two, which recounts the cast’s appearance at PaleyFest to celebrate the success of the revival. Click here for Part Three, which reviews how the revival wrapped up the series in May 2020.
When it comes to Will & Grace, there are several numbers that illustrate the show’s legacy and impact.
- 246: The number of episodes the show aired over 11 seasons (8 during its original 1998–2006 run and 3 during its 2017–2020 revival).
- 96: The number of Emmys the show was nominated for during its run. Only 5 comedy series in history scored more nominations — Cheers, Frasier, M*A*S*H, The Simpsons, and 30 Rock. The show won a total of 18 Emmys during its run. Only 6 comedy series in history scored more wins — Frasier, The Mary Tyler Moore Show, Cheers, The Simpsons, Modern Family, and All in the Family.
- 21: The number of Screen Actors Guild Award nominations the cast received. The only comedy series to score more nominations were Frasier, 30 Rock, and Everybody Loves Raymond. It won 7, a feat bested only by 30 Rock.
- 3: The number of comedy series that ever scored an Emmy for every single one of its regular cast members (All in the Family, The Golden Girls, and Will & Grace).
But here I am more interested in the number 16. That’s the number of holiday episodes the showed aired during its run. (Note: Only 13 are listed below because there are three sets of two-part episodes included.) The holiday representation is broken down as follows — 6 were about Thanksgiving, 5 were about Christmas, 2 were about Valentine’s Day, and 2 were about Halloween. The episodes vary significantly in terms of quality and in terms of how central the actual holiday itself was to the respective episode, but the holiday episodes listed below contain a disproportionate amount of the series’ best episodes. Below, I revisited them all and give my ranking, along with reviews, episode grades, and my favorite lines from each episode. (Note: At the time of writing, the entire series of Will & Grace was available for streaming on Hulu and for purchase on iTunes.)
13.) “It’s the Gay Pumpkin, Charlie Brown” (Season Five). The weakest of Will & Grace’s holiday episodes, this Halloween outing came after the whole universe of the show was upended following Will and Grace’s plan to have a baby together being upended by the arrival of Leo (Harry Connick Jr.) as a new love interesting for Grace. It is a painfully uneven outing featuring three plot lines of wildly varying tone and quality. In the best, a guilt-ridden Karen decides to confess her almost-affair to Stanley only to discover that he is having an actual affair, prompting her to leave him. In the worst, there is a woefully underdeveloped, largely unfunny, and awkwardly acted plot line with Leo bringing a cranky Will and Grace on a Halloween biking trip in the Catskills. Will and Grace come off as exceedingly unlikeable and Connick Jr. struggles to fit in with the ensemble. Somewhere in the middle is the absurd but mildly amusing plot line with Jack opening up a cafe in the hallway outside of his apartment. As was often the case when Will & Grace stumbled, Megan Mullally saved the day with a superb performance. Favorite Lines: Jack to Will re: his diminutive new boyfriend: “What you have is a pocket gay…the perfect travel size homosexual.” Grade: C+
12.) “Boo! Humbug” (Season One). The show jumped right into holiday episodes, with its first one arriving only five episodes into the series. The episode centers on two Halloween-themed plot lines. The significantly better one involves Jack and Karen going out on the town for Halloween, where Karen becomes a big hit with some drag queens. The much weaker one, which brings the episode down, finds Will and Grace saddled with babysitting Will’s client’s two kids on Halloween. Unfortunately, their first Halloween episode marks the weakest episode of the first season. Favorite Lines: Will, discussing director Ingmar Bergman: “I am very excited in a bleak, existentialist, void-y kind of way.” Grade: C+
11.) “All About Christmas Eve” (Season Five). Although it is a crisply paced episode, it underwhelms as a result of a very weak script that reduces Jack and Karen to one-dimensional cartoons as they sit in Karen’s posh hotel room and force service people to partake in Christmas caroling and other festivities with them against their will. It gets some genuine laughs, but it is cruel and contrived. In contrast, the dynamic between Grace using Will as a backup when her boyfriend is unavailable (this time for a performance of The Nutcracker) is painfully realistic. Nevertheless, it is deeply uncomfortable and somewhat unsatisfying in its resolution. The episode never really coheres, the laughs it does have are cheap, and it lacks the holiday spirit. Favorite Lines: Jack: “There are poor people who dream their whole lives of a meal like this” Karen: “I know what we should do. Let’s take a picture of us eating it and show it to them” Jack: “Wow Karen you are like a female Jesus.” Grade: C+
10.) “Christmas Break” (Season Seven). This middling outing is by no means bad, it just never really gels into anything particularly funny, clever, or touching. Will and Grace’s plot line involving Grace accidentally breaking one of Will’s mother’s beloved figurines looks great on paper, but doesn’t work particularly well in execution. Outside of Blythe Danner’s typically wonderful performance, it falls flat, with only a few good one liners and a predictable trajectory. Luckily, Karen and Jack’s storyline elevates things slightly as the show remembers that instead of using A-list guest stars they can always revisit past plot lines that were never dealt with properly — such as Karen’s relationship with her stepchildren. When her stepdaughter Olivia shows up for Christmas, Karen tries to pawn her off on Jack and then becomes jealous when they bond. Favorite Lines: Grace: “So that’s it? I’m going to just let her hang for my crimes? Well, she’s German so we’ll just call it even.” Grade: B
9.) “Dance Cards and Greeting Cards” (Season Seven). Compared to the show’s best farces, the dialogue isn’t quite as sharp and the laughs aren’t quite as big here. But it nevertheless is a solid episode with a clever-setup. Karen heads to her country club for their annual Valentine’s Day ball and her blind date turns out to be her high school nemesis Scott Woolley (Jeff Goldblum). He endears himself to her while saving her from Beverly Leslie’s ridicule (which allows Leslie Jordan to make another brilliant guest appearance). Meanwhile, Will and Jack have amusing scenes with the legendary Chita Rivera and Michelle Lee as a lesbian couple who helps them defy Beverly Leslie’s ban on same-sex dancing at the ball. Meanwhile, Grace meets a greeting card writer named Nick in a storyline that plods for a bit but quickly accelerates due to the wonderful chemistry between Debra Messing and supremely charming guest star Ed Burns. The dialogue could have been snappier and the two plots could have gelled better tonally, but it works well enough. Favorite Lines: Karen: “Black, white, gay, straight, what’s the difference? We all finish ourselves off in the end.” Grade: B+
8.) “Jingle Balls” (Season Four). This is a prime example of how so many Will & Grace episodes (and sitcom episodes more generally) suffer from a marked discrepancy in quality or tone between the A- and B-stories. The A-story involving Jack having to dress a Christmas window at Barney’s for his draconian boss (hilariously played by indie film icon Parker Posey) is superb. Karen’s attempts to help are uproarious and feature some iconic moments, but the real strength of the episode is the way that Grace finally comes through for him at the end. The twist achieves a level of warmth and heart that this show rarely achieved. Unfortunately, Will’s subplot about being ashamed of how effeminate his ballet dancer boyfriend is had the potential to cover interesting thematic territory yet devolves into cheap jokes and one-liners. It ultimately underscores rather than combats the internalized homophobia that his character suffers from. Favorite Lines: Karen: “It’s Christmas, for goodness sakes. Think of the baby Jesus. Sitting up there in the tower letting his hair down so that the three wise men could climb up it, spin the dreidel, and see if there are six more weeks of winter.” Grace: “Where did you get that? The Bartender’s Bible?” Grade: B+
7.) “A Gay Olde Christmas” (Season Nine). When I heard that the Will & Grace revival was following up the best episodes of its run (“Rosario’s Quinceanara,” which chronicled the aftermath of the death of Karen’s beloved maid Rosario) with a fantasy episode that transported the cast to turn of the 20th Century New York City, I expected the worst. I feared that the show, which grew wildly uneven in the later seasons of its initial run, was going to be repeating the same mistakes of the past by going too broad and cartoonish. But against all odds, it works amazingly well. The episode is centered on a disastrous Christmas Eve, in which the gang ends up at an immigrant museum so that Grace can pee. They begrudgingly take a tour and the majority of the episode plays out the story of the immigrant family the museum centers on with the cast depicting them. It sounds ridiculous — and it is — but several things work terrifically well. All four principal actors are perfect, particularly Eric McCormack as the stuffy closeted landlord and Megan Mullally as the poor Irish single mother. And then there’s the fact that the script works on multiple levels. First, it’s filled to the brim with hilarious one-liners. Second, it cleverly mirrors the character dynamics and plot developments of the series. And third, it provides a great deal of social and political commentary about the long history of bigotry toward women, gays, and immigrants. It’s too ridiculous to be a true classic, and many of the jokes are cheap and obvious, but it’s an utterly hilarious episode. Favorite Lines: John (Jack) to Carolyn (Grace) re: Will (Billem): “He wouldn’t enjoy it with any woman. That’s what I discovered. He’s a sweeper of chimneys. A snake charmer. He only travels by tunnel. He’s a mustache bumper. He rubs the silverware without a cloth. He plays the flute of the damned. He’s a homo!” Grade: A-
6.) “A Little Christmas Queer” (Season Eight). Another hilarious holiday outing for the gang, this episode finds them trucking to Connecticut for Christmas at Will’s mother’s house, a set up that facilitates several excellent elements. First, it gives viewers another chance to indulge themselves in the sheer awesomeness of Blythe Danner’s Emmy-worthy performance as the caustic and cold Marilyn Truman. Second, it delves into some atypically nuanced emotional territory, as Will grows frustrated that his mother is far more accepting of his presumably gay nephew than she ever was of him. Third, it gives the entire ensemble a chance to be together in the same scenes, which is usually when they do their best work. Subplots involving Karen bonding with Will’s niece and Grace rekindling her fling with Will’s brother also work well, making this one of the best episodes of Season Eight. Favorite Lines: Will re: his mother: “She was so thrilled that Christmas that I asked for two GI Joes because she thought I was building an army. But then she realized I was building a home.” Grade: A-
5.) “Queens for a Day (Parts One and Two)” (Season Seven). Two of the many things that Will & Grace excels at are Thanksgiving episodes and screwball farce. When those things come together it’s a thing of real beauty. The generally lackluster seventh season got an incredible jolt with this two-part classic that finds the quartet heading to Queens for Thanksgiving with Will’s boyfriend Vince’s family. Every member of Vince’s family is nuanced, well-written, and well-performed, with Jamie-Lyn Sigler (The Sopranos) and gifted character actors Lee Garlington and Robert Costanzo turning in superb work. The main quartet is on fire as well, with McCormack and Hayes delivering some of their best work of the season. Although the plot lines occasionally veer into the absurd or vile (e.g., the borderline statutory rape of Grace and Karen’s plot line), it is never anything less than hilarious for a second with razor-sharp dialogue that matches the committed performances. This is one of the finest outings of Will & Grace’s later seasons. Favorite Lines: Jack to Vince: “Your parents have done everything right. They raised all their kids gay!” Grade: A
4.) “Moveable Feast (Parts One and Two)” (Season Four). This exquisitely plotted ensemble outing has each of the four main cast members heading to their families on Thanksgiving before settling in for their own Friendsgiving. During the journey, Will grapples with his status as the favored son of his icy mother (Blythe Danner), Jack stews about perceived slights from his neglectful stepfather (Beau Bridges), Grace confronts her vain and hurtful mother (Debbie Reynolds), and Karen is livid when Stan tells her that he wants her to sleep with other men while he finishes his prison sentence. Each plot line is pulled off with a great balance of comedy and drama, and the performances of the main cast and the guest stars are superb. Just when you think the episodes have reached their comic height, Rosario convinces them to do one more round and wrap up unfinished family business to detract from the fact that she ate the whole turkey. Favorite Lines: Bobbi Adler re: fame: “30% is talent, 70% is luck of the draw” Jack: “That’s so depressing. You want to believe that sexual favors at least play some role.” Grade: A
3.) “A Chorus Lie” (Season Four): Calling this episode a holiday episode is a bit of a stretch, but given that one of the two major plot lines occurs at a Valentine’s Day ball it warranted inclusion. This extra-long outing easily ranks as one of the series’ very best episodes. Both storylines are perfection, the script may just be the sharpest and wittiest the writers ever created, andJames Burrows directs the hell out of the episode. The superb B-story finds Karen bringing an oblivious Will to her country club’s Valentine’s Day ball as her gigolo. The plot line features perhaps the most memorable appearance of the ever-brilliant Leslie Jordan as Karen’s nemesis Beverly Leslie. Then there’s the main storyline, in which Matt Damon plays a straight man posing as a gay man to defeat Jack for a spot in the New York City Gay Men’s Chorus. Jack enlists a flirtation-challenged Grace to seduce Damon in order to “prove” his heterosexuality (and thus disqualify him). Every second of the storyline is brilliantly written and performed, with Hayes and Messing doing some of their finest comedic work of the show’s run and Damon proving one of the very best of the dozens of A-list guest stars the series had during its run. Favorite Lines: Karen: “I don’t want you to be intimidated by all of these rich society types. Remember, they are just like you, only infinitely better.” Will: “Oh, Karen, I am no more intimidated here than you would be in a room of people who were getting into heaven.” Grade: A+
2.) “Homo for the Holidays” (Season Two). One of the funniest and most touching episodes the series ever produced, this one won Sean Hayes his sole Emmy for the series. It should have won an Emmy for Alex Herschlag’s flawless script as well. The episode deepens both Jack as a character and his relationship with Will as it is revealed that Jack has never come out as gay to his mother (guest star Veronica Cartwright). A perplexed Karen and Grace provide hilarious comic relief as they fight over who should be his beard, whereas Will digs deep to provide Jack with the validation and support that he needs. It is brilliant from start-to-finish with unforgettable dialogue, huge laughs, and a performance from Sean Hayes that is one of the best of the series. Favorite Lines: Karen to Judith re: Jack: “I think you’re missing the silver lining. When you’re old and in diapers, a gay son will know how to keep you away from chiffon and backlighting.” Grade: A+
1.) “Lows in the Mid-Eighties (Parts One and Two)” (Season Three). My vote for the best episode of Will & Grace’s run is this brilliant outing that flashes back to when Will first came out in college. Eric McCormack won a very well-deserved Emmy for his tour de force performance as he decides while meeting his then-girlfriend Grace’s eccentric family over Thanksgiving that it’s finally time for him to come out. Debra Messing nearly matches his work as Grace goes from deliriously in love to comically exasperated to utterly heartbroken. Sean Hayes is hilarious as Jack tries to help Will through the coming out process. And the late, great Debbie Reynolds gives one of her finest performances on the show as Grace’s overbearing mother. Meanwhile, we learn about the absurd antics that Karen was up to in the 1980s. In addition to having huge laughs and genuinely emotional drama, the episode is also terrific fan service as it explores the origin of numerous elements of the show — Rob and Ellen’s friendship with Will and Grace, Will and Grace’s college romance, Will and Jack’s friendship and almost romance, Karen and Rosario’s friendship, Grace’s family problems, and the first woman Will slept with. The 1980s aesthetic is superb with period-perfect and hilarious hairstyles, clothing, and art direction. The best thing about this episode is that it never lets the one-liners, costumes, or fan service detract form its raw emotional core. When Grace asks Will, “How come you couldn’t have made it awful with me?” it is a true gut-punch. Everything great about Will & Grace culminated in this two-part episode. Favorite Lines: Will to Jack: “I owe you everything. In this past year, you’ve been like my sherpa leading me through the Himalayas of Him-a-laying.” Grade: A+
Follow the author of this article on Medium and Twitter.
Check out other articles about classic holiday entertainment by this author:
- Why “While You Were Sleeping” Is an Underrated Christmas Classic
- A Festive Guide to 2020’s New Christmas Streaming Options
- The Astounding Quarter Century Ascent of “All I Want for Christmas Is You”
- A Firsthand Account of Surviving the 1978 “Star Wars Holiday Special” Disaster
- Friends: The One with the Thanksgiving Episodes
