The 12 Best Holiday Movies For People Who Want Something Totally Different

The holiday season is here, even if you wish that the Christmas season didn’t truly start until after Thanksgiving. (In 2024, at least, that would mean that the season would be limited almost entirely just to December.) Naturally, movie studios have already begun to foist holiday movies upon the world, whether it’s Hallmark-style straight-to-streaming fluff like “Hot Frosty” or the extremely big-budget action-adventure “Red One,” starring Dwayne Johnson and Chris Evans as an unlikely duo who have to team up to rescue none other than Santa Claus himself from being kidnapped and ruining the holiday altogether. But for those of us who may love films but want something a little different out of the movies that ring in the extended holiday season from Thanksgiving all the way through New Year’s Day, try out these 12 movies for size. We won’t get into any standard-issue “Is ‘Die Hard’ a Christmas movie?” debates in this list. (The answer is yes, by the way.) Instead, let’s just look chronologically at these 12 very different kinds of holiday movies.

Among the many truly remarkable aspects of the 1937 film “Make Way for Tomorrow” is the dexterity of its director, Leo McCarey. The same year that he directed this genuinely heartbreaking drama about the forced dissolution of a long relationship between an elderly couple during the Great Depression, he also directed the brilliant screwball comedy “The Awful Truth,” and was only a few years from having directed the best-ever Marx Brothers comedy, “Duck Soup.” The point here is that while McCarey has plenty of comedy chops, he goes all in on the pathos in “Make Way for Tomorrow,” which is the kind of calmly tragic film that almost sneaks up on you in how effective it is at making you bawl your eyes out. Although it arrived in the middle of the Hays Code era, you’ll find no saving grace in how this film concludes, as an elderly married couple makes peace with the fact that because of the Depression and their not-terribly-kind children, they’re forced to separate for good and will likely never see each other again. And it’s set against the backdrop of Christmas. God bless us, everyone!

Nothing says the Christmas season like a dramedy in which the lead character sublets his eponymous apartment to his bosses so they can maintain affairs away from their wives’ prying eyes, and where one of those Other Women realizes her lot in life and nearly dies by suicide via overdose on Christmas Eve. Who else is in the spirit of the season now? Glibness aside, for all the many wonderful films he directed, Billy Wilder didn’t do much better than his 1960 classic “The Apartment.” It’s no surprise that the film won big at the Oscars, winning Best Picture, Best Director, and Best Original Screenplay. If anything, it’s shocking that neither Jack Lemmon nor Shirley MacLaine won for their excellent performances as CC Baxter and Fran Kubelik, the aforementioned apartment subletter and Other Woman, respectively. They bring an immense amount of life and pathos to their characters, Wilder does an incredible job of capturing the working world of New York City at the start of a new decade, and the film has only aged like the finest of wine. It’s not going to be the cheeriest holiday film, but you simply cannot do better than “The Apartment.”

Nearly 40 years later, “Brazil” remains one of the best dystopian films of all time, if not the very best. From Monty Python alum Terry Gilliam, “Brazil” takes its cues from the legendary George Orwell in depicting a society that is only slightly removed from our own with its wildly inefficient government bureaucracies, its charmingly evil corporate toadies, and its focus on a hapless leading man who so badly wants to escape into his fantasies of flying freely through the air with a beautiful woman by his side that he eventually lives in those fantasies permanently. And yes, though it may be easy to forget with its livewire action, dark comedy, and fanciful set and costume design, “Brazil” does take place around the Christmas holiday (though even Gilliam may not have been able to imagine the ridiculous way in which cultural pundits bloviate about the use of the phrase “Happy Holidays” instead of “Merry Christmas” in the real world). When we think of traditional holiday movies, we think of emotional pick-me-ups, and “Brazil” is the exact opposite tonally. If you’re looking for an all-too-prescient commentary on how we live, and one that proudly sidesteps an upbeat finale, all while being set at the holidays, this is your answer.

There’s always something a little off about watching a movie set during a distinctive time of year at a different time of year, as if your mental calendar has been shook up for little reason. It’s rarer for studios to release films set during one holiday season at a different time of year, but Stanley Kubrick’s absolutely brilliant final film, “Eyes Wide Shut,” is a very rare beast indeed. When it arrived in theaters in the middle of July 1999, audiences knew very little about what to expect from “Eyes Wide Shut,” outside of a brief and bombastic teaser reminding us that it starred mega-famous Tom Cruise and Nicole Kidman (back when they were still married), and that it apparently would offer some level of salaciousness. The end result is, deliberately, less about the sexy times between Dr. Bill Harford and his mildly bored wife Alice, and more about what happens when Bill learns of a specific sexual fantasy his wife has harbored, and how it sends him down a rabbit hole of perversity in the New York City area, culminating in a dark and disturbing masked orgy. And it’s all set at Christmastime, with an opening sequence at a glittery holiday party, and the final scene taking place at a toy store as Bill and Alice shop for their daughter’s presents (and Alice delivers one of the best final lines in film history). “Eyes Wide Shut” will not put you in the Christmas spirit, but that most wonderful time of year is undeniably a big part of what makes this film so unnerving, alien, and unforgettable.

The cutthroat world of corporate finance circa the 1980s is not the place for a bright, upbeat holiday movie, and yet, here we have “American Psycho.” Based on the controversial Bret Easton Ellis novel, “American Psycho” is, like the aforementioned “Brazil,” a particularly prescient satire, though one that is intended to exist within the real world. Christian Bale stars as Patrick Bateman, an outwardly driven and determined banker whose lengthy monologues on the power of musicians like Huey Lewis and Phil Collins is matched by his seeming ability to cut down his rivals by literally killing them off. (Or is it all in his head?) Whether or not Patrick actually does murder people for offenses like having better business cards, the glitz and light of the Christmas season, during which the film is set, can’t do much for his twisted mentality and his growing inability to separate reality from blood-soaked nightmare fantasias. Bale has rarely been better, believably adopting a smug demeanor that can quickly turn twisted and the Christmas lights in the background only heighten this film’s effectively disturbing ethos.

Shane Black loves setting his films during the Christmas season, almost as much as he loves telling stories that have absolutely nothing to do with the Christmas season. (That he was even able to have “Iron Man 3” set during the Christmas season is a testament to his ability to sneak in his personal preferences into the Marvel Cinematic Universe.) The film that served as both his return to form as well as proof positive that Robert Downey, Jr. was once again a bankable star, paving the way for him to become the aforementioned Iron Man, was “Kiss Kiss Bang Bang,” a playful neo-noir comedy in which Downey played Harry Lockhart, a shifty burglar who all but falls into the world of acting and gets involved in a big Hollywood conspiracy all while teaming up with an irascible cop (Val Kilmer) and falling for his old childhood crush (Michelle Monaghan, at one point embodying the holiday spirit with a revealing teddy). If you wanted, you could make a whole meal of totally different holiday movies all from the mind of Shane Black, but “Kiss Kiss Bang Bang” is just about the purest and most effective choice of all.

The mid-2000s proved to be a very fruitful time for both director David Cronenberg and his frequent collaborator Viggo Mortensen. A couple years after their first massively successful partnership on the excellent “A History of Violence,” they reunited on a tough-as-nails crime drama set amidst the merriest holiday of all. “Eastern Promises” was instantly well-known for a particularly visceral hand-to-hand combat scene in which Mortensen’s mobster Nikolai takes on a group of heavies while in the middle of a bath house (and while naked). Although the film is arguably not the most downbeat option among those titles in this list, “Eastern Promises” is far from the kind of film you associate with the Christmas season. If anything, the film feels particularly cool and icy, befitting Cronenberg’s chillier style of filmmaking, and the Christmas setting makes for a sharp difference with the gangland-war story taking place in the winter. “Eastern Promises” is, like its main character, tough as hell and unrelenting even in the harshest of conditions.

There are few things about the main character of Martin McDonagh’s debut feature “In Bruges” that are undeniably clear, but one of them is that he absolutely hates being … well, in Bruges. For the haunted lead, played masterfully by Colin Farrell, it’s bad enough that he can’t stop thinking about the fateful murder that he accidentally committed while in the line of duty as a hitman (he didn’t mean to kill a child, but things happen). It’s worse that his partner (Brendan Gleeson) loves walking around Bruges, but even more painful that they happen to be hanging out and waiting for further instructions from their grouchy boss (Ralph Fiennes) during the Christmas season. In some ways, “In Bruges” is the perfect Christmas film for the Grinchiest person in your life (unless that person is you), because Farrell’s lead character makes no bones about what he so strongly dislikes about the festive locale in which he’s holed up, and if you can’t stand the spirit of the season, you may find that his complaints resonate quite strongly.

It’s hard not to associate the Christmas season with romance, in part because it’s the time of year when you want to spend time with the ones closest to you. But sometimes, romance can be challenging, and there are few more effective examples of just how challenging than Todd Haynes’ tender and heartbreaking 2015 film “Carol.” Based on the novel of the same name by Patricia Highsmith, “Carol” depicts a queer romance between the eponymous housewife (Cate Blanchett) and Therese (Rooney Mara) a young photographer, who meet each other at a New York department store and soon can’t help running into each other and falling in love. As fraught as the world may be today for members of the LGBTQ+ community, it was even harder for those same folks during this film’s setting of 1952. It’s especially hard for Carol, seeing as she’s married to a fairly unpleasant man (Kyle Chandler) and has a young daughter to boot. Haynes precisely and cautiously depicts the affair between Carol and Therese with patience and empathy, but never without unwavering honesty, meaning that the holiday setting only heightens the ups and downs of these women’s relationship, even with a slightly upbeat hint of a conclusion.

Filmmaker Sean Baker is riding high thanks to the success of his independent film “Anora,” which focuses on a sex worker and her unexpected relationship with an Eastern European man. Baker has excelled over the last decade at making films set in a lower class structure within America, but doing so with a non-judgmental eye and a strong sense of empathy, like he did in his excellent 2017 film “The Florida Project.” But before he shot that Walt Disney World-advanced flick, Baker made “Tangerine,” a raucous, lively comedy set on Christmas Eve in Los Angeles and filmed entirely with iPhones. “Tangerine” focuses on Sin-Dee (Kitana Kiki Rodriguez), a transgender sex worker on a tear when she learns her boyfriend/pimp (James Ransone) is cheating on her with a cisgender woman. Contrary to its ultra-low budget, “Tangerine” has a remarkable eye for visual details and character, and feels as vast as the City of Angels itself. “Tangerine” is also as shrewd and empathetic as anything else Baker has made, and a bittersweet depiction of relationships (among friends and lovers) at the time of year when being lonely can make the holidays hit especially hard.

The holiday season extends for months (at least in America), so that when November begins, it feels like the beginning of a marathon between Thanksgiving, Hanukkah, Christmas, New Year’s Eve, and a few other holidays thrown in for good measure. Paul Thomas Anderson’s fascinating, enigmatic, and haunting film “Phantom Thread” covers a bit of chronological ground, but it too has a key sequence at a major New Year’s Eve party, which serves as a backdrop for the compellingly fractious relationship between celebrated fashion designer Reynolds Woodcock (Daniel Day-Lewis) and his latest paramour Alma (Vicky Krieps). Alma has vacillated between being in love with Woodcock and being absolutely frustrated by his exacting standards, his overly officious sister (Lesley Manville), and his seeming inability to let her be her own person. But as the second half of “Phantom Thread” charges headlong towards a surprising, darkly funny, and slightly perverse final scene, it also jumps around in time a bit to give us glimpses of the big New Year’s party, as a contrast between the other attendees having the time of their life and Woodcock and Alma having a more muted and low-key dance amidst the post-party revelry. “Phantom Thread” is an eerie film for many reasons, but its brief holiday setting only heightens its generally spooky pallor.

The very nature of a film about the late Princess Diana is guaranteed to be depressing and vastly opposite of what we associate with a holiday movie. Indeed, the 2021 drama “Spencer” from director Pablo Larrain, with Kristen Stewart playing Diana and revealing quite an impressive British accent to boot, doesn’t explore the tragic circumstances that led to her untimely death in 1997, but instead focuses on a brief period of her life in 1991 (specifically between Christmas Eve and Boxing Day) when she was struggling not only against the vagaries of the royal lifestyle, but also with her marriage to Prince Charles being troubled due to his affair with Camilla Parker Bowles. The festivities of the season are impossible to avoid yet feel particularly hollow to use (filtered through Diana’s reactions) specifically because of how little joy she’s finding in the life of a princess. Stewart and Larrain make for a powerful combo in front of and behind the camera, imbuing not only pathos into the life of Diana but actual three-dimensional depth, so that the enigmatic real-life figure feels vastly more human than the more officious, unemotional people surrounding her at the holidays.