1 30 Rock, "Ludachristmas"
30 Rock mostly killed it with guest stars (sit down, Hayek) but no one was deployed with such mischievous glee as Broadway dame Elaine Stritch, playing Jack Donaghy's mother Colleen. As the TV gang prepares for Ludachristmas (not just because Liz Lemon parties are mandatory), Colleen sets about ruining Christmas for the happy-go-lucky Lemon family---including Liz's 40-year-old brother Mitch who, due to a high school ski accident, still thinks it's 1985---just to fuck with Jack. (Spoiler alert: She does.)
2 The O.C., "The Best Chrismukkah Ever"
Seth Cohen is the forgotten dreamboat pop icon of our time, skinny and indie and witty, just like all our boys now. In 2003 he introduced the concept of the super-holiday Chrismukkah, which has "twice the resistance of any normal holiday" and is thus unruinable, though he nearly sabotages it himself by being a simpy wiener who won't choose between Summer and Anna. People were so stoked about this that Warner released The OC Mix 3: Have A Very Merry Chrismukkah, featuring holiday jams from The Raveonettes, Jimmy Eat World and Eels (but not Seth Cohen fave Death Cab, boo).
3 The Office, "Christmas Party"
Office Christmas episodes were always Very Special and though the show's signature brand of pathos and absurdity resulted in Meredith setting her hair on fire, party wars and Princess Unicorn ("my horn can pierce the sky") over the years, nothing beats the series' first installment, in which Jim gets Pam as his secret Santa and includes a confessional card---because the holidays are "the time to tell people how you feel"---which he jacks back at the last second (and ends up giving to her in season nine!).
4 The Simpsons, "Grift of the Magi"
When Springfield Elementary goes bankrupt, only Lisa has suspicions that its new owners may be a corporation using the students for holiday espionage ("our guest speaker was Phil from marketing"). As ever, she's not wrong, and Funzo---a cuddly creature with lots of firepower, programmed to ruin other toys---is at the core of the funniest holiday Simpsons ever, featuring an appearance from the late Gary Coleman, who---let's just say---is a few prawns short of a galaxy.
5 The X-Files, "How the Ghosts Stole Christmas"
Season six is not exactly a banner era of The X-Files, but at least this holiday installment did better than "Merry Christmas Scully, you have a daughter!(?)" like the one previous. This monster of the week ep finds Scully and Mulder doing psychological battle with cranky ghosts (Lily Tomlin and Ed Asner, perfect), harking back to the heralded, breezier times of "Jose Chung's From Outer Space" and "Small Potatoes."