9. Kiss Kiss Bang Bang (2005)
It would’ve been impossible to leave Shane Black off this list, and out of his whole body of work, Kiss Kiss Bang Bang remains the film that best embodies his singular style as a filmmaker, and the essence of cynical Christmas movies.
It’s not that Kiss Kiss Bang Bang doesn’t have lighthearted, funny moments. But this neo-noir comedy about a thief who comes to Los Angeles to act and gets involved in a murder plot is so sarcastic, so unconcerned with the supposed importance of the holidays, it actually wears its cynicism as a badge.
With a true comeback performance from Robert Downey Jr. that proceeded his rise to superstardom in Iron Man, and a hilarious supporting performance from Val Kilmer as a P.I. named “Gay” Perry, this crime story about Hollywood’s seedy underbelly is a must-watch for anyone looking for a Christmas movie without all the holiday sentiment.
10. The Family Stone (2005)
The Family Stone is exactly 103 minutes of almost unbearable tension. Starring Sarah Jessica Parker as Meredith, an uptight, old-fashioned businesswoman who doesn’t fit in with her fiancée’s hippie family, this is the kind of comedy that’s as painfully awkward as it is funny. Like most Christmas movies, it has a happy, if not bittersweet ending. But a lot of what leads up to that is a tough watch— including one excruciating dinner scene in particular.
Luckily, the rest of the movie’s solid ensemble makes it all worthwhile, with actors including Diane Keaton, Claire Danes, Dermot Mulroney, Craig T. Nelson, and Luke Wilson all costarring (Keaton of course also starred in a much less successful ensemble Christmas film with this year’s Love the Coopers.)
11. In Bruges (2008)
Rivaled only by Kiss Kiss Bang Bang in terms of Christmas crime stories, Martin McDonagh’s 2008 dark comedy about two criminals laying low in the film’s titular city has long been viewed as an underrated masterpiece.
No one mixes humor and pathos quite like McDonagh, and as a bonus, the movie also gets a career-best performance out of a fantastic Colin Farrell. As his protagonist, the charming and troubled Ray would tell you, Bruges may seem like a magical, Christmasy, fairytale city, but as In Bruges demonstrates, those qualities can also become pretty depressing under the right circumstances.
12. A Christmas Tale (2008)
No one does cynical quite like the French. Although in many ways, this comedic-drama from director Arnaud Desplechin could be the premise for an average American film.
A dysfunctional family gathers around the holidays, thanks to their matriarch (Catherine Deneuve,) who has made a dramatic announcement. But A Christmas Tale thoroughly transcends American clichés, capturing the emotion and frustration of the holidays in a distinctly different way. Try to watch it soon, before they announce a U.S. remake.
13. Rare Exports: A Christmas Tale (2010)
Rare Exports isn’t the only horror movie about Santa Clause ever made (see: Santa’s Slay,) but it is probably the most original.
In this little Finnish gem from first time feature director Jalmari Helander, a group of townies near the Korvatunturi mountains dig up a terrifying, hidden secret— Santa is real, he’s been locked up for ages, and he’s not the lovable fat man you’ve heard of. This is a fantasy story that’s scarier than you’d expect, and all the better for it.
14. Happy Christmas (2014)
This “mumblecore” comedy from Chicago indie director Joe Swanberg isn’t your typical Christmas movie in any sense. The rather thin plot centers on a 20-something screw-up named Jenny (Anna Kendrick,) who moves in with her brother (Swanberg) and his wife (Melanie Lynskey) after a break-up.
Watching the always-great Kendrick get into trouble is really the fun of the film, and Lynskey gives an equally great performance as her artistically repressed sister-in-law. But above all, the movie is a great reminder that even though Christmas is supposed to be a time for family, sometimes family is what makes Christmas so hard.
15. Tangerine (2015)
“What is Christmas like for our society’s most disenfranchised people?” That’s the question director Sean Baker asks with Tangerine, one of this year’s biggest Sundance hits and a minor indie sensation. Following two transgender prostitutes who walk a rundown section of the Santa Monica strip in Hollywood, and their misadventures leading up to Christmas Eve, Tangerine isn’t always an easy watch.
These women’s lives are dangerous, and the movie doesn’t stray away from that. But it also has a rich sense of humor, and there is a joy in watching leads Kitana Kiki Rodriguez and Mia Taylor bounce off each other, and off the strong ensemble cast that surrounds them. Extra trivia for movie nerds— the whole thing was shot on an iPhone 5. And it looks great.
16. Krampus (2015)
A film that probably owes a bit to Rare Exports, Krampus is literally a movie about the anti-Santa Claus.
Based on Austro-Bavarian folklore, this horror-comedy tells the tale of a demon who’s accidentally summoned to reek havoc upon one dysfunctional family’s Christmas. It’s a silly film, but not without a few decent frights, and several funny moments.
Author Bio: Chris Osterndorf is a freelance writer whose work has appeared on The Daily Dot, Mic, Salon, xoJane, The Week, and more. He currently lives in Los Angeles.