On December 5, Will & Grace is keeping the ancient sitcom tradition of the "holiday episode" alive with an episode set in 1900s New York. We'll have to wait to see how that pans out, but for now, enjoy the definitive ranking of all the Will & Grace holiday episodes to date!
“Boo! Humbug” (Halloween, Season 1)
When Will and Grace both refuse to go out with Jack for the “most important day of the year,” a.k.a. Halloween, he convinces Karen to be his date. Will and Grace get end up stuck babysitting for Will’s boss and Karen makes friends with a group of drag queens.
"It’s the Gay Pumpkin, Charlie Brown" (Halloween, Season 5)
Will and Grace join Leo for an outdoorsy, pumpkin-picking Halloween in the Catskills. Leo tries to set Will up with a pocket gay, but Karen leaves Stan after discovering he's had an affair.
"Christmas Break" (Christmas, Season 7)
Grace goes to Will’s mom’s (Blythe Danner) place for a holiday tea party and breaks one of her favorite tchotchkes. Karen’s stepdaughter comes to town and ruins her drunken Christmas plans—but then she gets jealous when her stepdaughter gets close with Jack.
"A Little Christmas Queer" (Christmas, Season 8)
The gang goes to visit Will’s family in Connecticut for the holiday. Will’s mom (played by Blythe Danner) is doing the most for entire episode, Grace hooks up again with Will’s brother and Jack takes Will’s possibly gay nephew under his wings.
"Lows in the Mid-Eighties" (Thanksgiving, Season 3)
Flashback to 1985, when Will was closeted and dating Grace. They visit Grace’s family for Thanksgiving and he proposes—to avoid sex—but after she tells her entire family they’re getting married, he comes out as gay. Extra points for the pitch-perfect vintage hair and clothes.
"Fanilow" (Christmas, Season 6)
Will misses Grace and Karen’s work holiday party to stand in line for Barry Manilow tickets. Grace catches her mom, who canceled on her, out to dinner with Jack. And everyone, especially Karen, share some great scenes with guest star Sara Gilbert.
"All About Christmas Eve" (Christmas, Season 5)
Grace has to deal with both leaving her friends behind to spend Christmas with Leo, who Will feels is replacing him as the main man in Grace’s life. Meanwhile, Karen and Jack spend a luxurious Christmas in a fancy hotel tormenting the staff.
"Queens for a Day" (Thanksgiving, season 7)
The gang goes to Queens to celebrate Thanksgiving with Vince’s family: Will vies for Vince’s mother’s approval, Jack befriends a closeted lesbian, and Grace and Karen fight for the attention of hot guy who turns out to be just a little too young for them.
"Jingle Balls" (Christmas, Season 4)
Will is secretly dating a man he’s embarrassed about. When Jack’s boss (Parker Posey) asks him to do the Barney’s Christmas window, he turns to his fairy godmother, Grace, for help.
"Homo For the Holidays" (Thanksgiving, Season 2)
Jack’s mother, Judith (Veronica Cartwright), drops in for a surprise Thanksgiving visit, and the gang learns he's not out to her yet. (Karen: “What is she, headless?”) AsKaren and Grace fight over their pretend relationships with Jack, Judith tells him a secret of her own: she doesn’t know who his real father is.
"Moveable Feast" (Thanksgiving, season 4)
While Rosario works on a Thanksgiving feast at Will's place, the gang take turns quickly visiting each other’s families. To stay on schedule, they use a egg time—leading to some hilarious goodbyes.