The Apartment (1960): Billy Wilder’s enduring satire of office politics — a lowly insurance clerk (Jack Lemmon) makes extra money by lending his New York City apartment to various philandering colleagues and bosses — is also about how loneliness can be most acute during the holiday season. For those who’ve yet to experience The Apartment, we’ll not reveal Lemmon’s Christmas Eve surprise, which is delivered via a moving, never-better Shirley MacLaine.
Bad Santa (2003): Billy Bob Thornton plays an alcoholic, foul-mouthed, deliciously cynical shopping mall Santa in this black-comic subversion of feel-good holiday movies. The sentimental finale seems out of place, but Bad Santa does unblinkingly delve into the commercialization of Christmas, the limited job market for midgets and the pain endured when one’s balls are kicked.
Beautiful Girls (1996): Yes, one of its central concerns is about the way men idealize ungraspable women (hence the title), but, more importantly, very few movies capture the feeling of going home to small-town America during the holidays as well as Ted Demme’s often underappreciated gem — from dealing with family and old friends to the pleasures of revisiting vintage childhood landmarks.
Local tidbit worthy of note: It features a live bar-band performance by The Afghan Whigs.
Big Night (1995): An orgiastic display of food that just might be the best movie ever about merits of cooking as a form of art. It’s also incisive about the perils of the restaurant business, the problems of brotherhood and the ways food can bring people together (if only fleetingly). And, for the purposes of this list, has there ever been a better movie to get once juiced about a holiday meal?
A Christmas Tale (2008): A fractured Parisian family reunites at Christmas when it becomes apparent its matriarch (Catherine Deneuve) is suffering from a potentially fatal disease. Talented French filmmaker Arnaud Desplechin uses that serious matter to jump off in a variety of directions, all of which display his deft technical skills while never blunting his tale’s richly layered emotional impact.
Gremlins (1984): Ever-imaginative genre-juggler Joe Dante injects a smorgasbord of anarchic merriment in this story of a Christmas gift gone awry. For the era in which it was made, the special effects are remarkable — a reminder that handmade puppets are always better than soulless computer-generated images.
Metropolitan (1990): Set during Christmas vacation among a pack of young, upper-crust socialites in the late 1980s, Whit Stillman’s debut is a window into a world that, more than 20 years after its release, still seems fresh and unique, its depiction of class snobbery and adolescent anxieties delivered with illumination and piercing wit.
The Nightmare Before Christmas (1993): Bored with his role as the Pumpkin King of Halloween, this year Jack Skellington wants to team up with his buddies to give Santa Claus a helping hand, leading to an unintended crisis that puts Christmas in jeopardy. Producer Tim Burton often gets the most credit for this stop-motion wonder, but director Henry Selick and screenwriter Caroline Thompson should get just as much attention for their role in a near-impossible feat: crafting a new, wholly singular fairy tale for the holidays.
The Shop Around the Corner (1940): “Never did I make a picture in which the atmosphere and the characters were truer,” ace director Ernst Lubistch once said of his The Shop Around the Corner, a uncommonly convincing romance that’s as graceful and beguiling as the day it surfaced more than 70 years ago. The atmosphere is snow-dappled Budapest during Christmastime; the characters are a pair of shop clerks (Jimmy Stewart and Margaret Sullavan) who become intertwined in a battle of the sexes fraught with mix-ups and misunderstandings. Pure magic.
Trading Places (1983): Remember when Eddie Murphy’s electric smile, staccato laugh and lacerating wit made him the toast of Hollywood? Yet the most curious element here is the unexpected empathy generated by Dan Aykroyd as a smug, Mitt Romney-esque business dude whose billionaire bosses, in a bet about whether breeding makes a difference, toss him aside for Murphy’s street-smart kid in this entertaining take-down of Wall Street that more than once brings to mind A Christmas Carol. Signature visage: a drunken Aykroyd in a soiled Santa outfit.©