Cynical But Sweet Christmas Movies to Get You in the Holiday Mood

From the site that brought you out-of-the-box Thanksgiving specials and seriously messed-up Christmas specials, we're here to put you in the holiday spirit with some cynical, yet sweet Christmas movies.

Cynical But Sweet Christmas Movies to Get You in the Holiday Mood

NightBefore

 

Christmas is nearly here. It can all be a bit overwhelming. The singing. The dancing. The visions of sugar plums. And goodness, let’s not get started on the figgy pudding. Sometimes people need something new.

Viewers aren’t total Grinches, though. They don’t hate Christmas. They just want a little sour to cut through the sweetness. A bit of cynicism to make the happy endings feel that much better, that much more earned.

If you feel like one of the viewers described above, you’ve come to the right place. We have the 12 Cynical But Sweet Christmas Movies to Get You Through the Holidays.

Image Credit: Sony Pictures Releasing. 

The Apartment

Apartment

Bud Baxter (Jack Lemmon) has found the secret to climbing the corporate ladder: letting his bosses use his apartment to carry on their illicit affairs. Bud largely can swallow his moral qualms as the positive references rack up until the personnel director Jeff Sheldrake (Fred MacMurray) demands to be the next lodger. It’s then that Bud learns his office crush, Fran (Shirley MacLaine), is Sheldrake’s mistress.

As Bud tries to reconcile himself to either giving up on romance or career success, Fran attempts to come to terms with being not just the other woman, but only the most recent of Sheldrake’s other women. Emotional pain, suicidality, job loss, and broken promises follow.

However, as the New Year rolls in, the two somehow find a deck of cards, a bottle of champagne, and the promise of a happy ending.

Image Credit: United Artists.

Bad Santa

Bad Santa

Every year Willie (Billy Bob Thornton) and Marcus (Tony Cox) run the same scam. Willie gets a job as a mall Santa, Marcus as an elf, and they spend a month getting to know the ins and outs of the place. By the end of the season, they’ve stolen enough to live high on the hog for eleven months. Then, come December, they’ll meet up to do it all over again.

Unfortunately, Willie’s drinking and womanizing have taken a toll on their partnership. To make matters worse, Willie has more or less stopped caring about anything, even getting the money. He thus finds something even worse to be than a drunk, philandering thief who pretends to be Santa to steal. Instead, he’s a drunk, philandering thief who pretends to be Santa to steal, and he’s gotten quite bad at it.

Somehow, even in this state, Willie convinces a young boy Thurman that he’s the actual Santa (Brett Kelly) and the kindhearted Sue (Lauren Graham) that he’s worth having sex with. Of course, creating this trio of mismatched outcasts doesn’t make Willie a good man, but he is a slightly better one.

The ending somehow managed to both affirm Willie as a fairly repugnant person AND that there may be some decency in him yet. It’s a hard trick to pull off remaining loyal to the film’s pitch-black tone and give you hope, but Bad Santa does it. F*** me, Santa indeed.

Image Credit: Columbia Pictures. 

El Camino Christmas

El Camino Christma
El Camino Christmas

Eric Roth (Luke Grimes) came to town for just one reason. He wanted to see if his father, who he had never met, still lived there. Somehow that leads to him getting beaten and arrested by a drunk, crooked cop Carl (Vincent D’Onofrio), and the gullible deputy Billy Calhoun (Dax Shepherd). Even more confusing is how that spurious arrest puts him on the path to being smack dab in a hostage situation in a local liquor store with Larry (Tim Allen), a vet who drinks heavily to manage his PTSD, a young single mom Kate (Michelle Mylett) and her possible delayed or disabled son, a bleeding Carl, and the liquor store owner Vicente (Emilio Rivera).

The cops are incompetent, a couple of the hostages are actively intoxicated, several individuals are excessively casual about firing their guns, and at least one person isn’t leaving that store alive. But it still manages to deliver some bittersweet fuzzies in the end, one of Tim Allen’s rare good live-action roles and far more laughs than the plot description would suggest.

Image Credit: Netflix.

Gremlins

gremlins

Randall Peltzer (Hoyt Axton) only wants to surprise his son Billy (Zach Galligan) with a wholly unique Christmas gift when he stumbles upon a mogwai in an antique shop. While the creature in question, Gizmo, is adorable, he has three rules. Unfortunately, with an assist from a clumsy friend and a faulty alarm clock, Billy breaks two almost immediately. As a result, lizard-like Gremlins who destroy property, maim, and kill with surprising skill and amorality overrun the small town quickly.

That, however, isn’t the most profoundly cynical aspect of Gremlins. For that, you have to wait for Kate (Phoebe Cates)—Billy’s girlfriend—to explain why she doesn’t like Christmas. It is a thing of mean-spirited, heartless comedy wonder, made all the better by Cates deadly sincere delivery.

The uplift comes from the final confirmation that, despite all the chaos and bloodshed, Billy and Gizmo have bonded, and someday soon, perhaps, Billy will be capable of effectively looking after the little guy.

Image Credit: Warner Bros. 

Happy Christmas

Happy Christmas

Just dumped Jenny (Anna Kendrick) is a bit of a mess. In the hopes of finding solid ground, she moves in with her brother Jeff (Joe Swanberg, also writing, directing, and editing), his wife Kelly (Melanie Lynskey), and their son, Jenny’s nephew. Instead, she quickly upends their life, drinking far too much, smoking weed and seducing the babysitter, and forcing the couple to acknowledge they’re not as happy as they portray. Plus, Jenny’s friend Carson (Lena Dunham) is just around all the time. And all this during the stress of the holiday season.

Still, Jenny’s presence unlocks something in Kelly. A scene where Jenny and Carson help Kelly write the moment the character in her novel loses her virginity is delightfully dirty and grounded in a true moment of family and friend bonding. The sex makes it funny. The witnessing of three people pouring themselves into helping each other gives it heart.

Image Credit: Magnolia Pictures.

Home Alone

Home Alone

Any way you slice it, Home Alone is the story of an abandoned boy who defends his enormous suburban home from crooks looking to take advantage of people going away for the holidays but stealing everything not bolted down. Moreover, he protects his house with such notable brutality that the thieves end up with concussions, nail wounds, burns, and an assortment of bodily contusions.

The family unit reasserts itself and the thieves arrested, so there’s the happy ending. Until then, though, the movie drips with cynicism.

Image Credit: 20th Century Fox. 

It’s A Wonderful Life

its a wonderful life

I know what you are thinking. And you’re mistaken. It’s a Wonderful Life has a happy ending, for sure, but while we’re getting there? We see some pretty grim stuff along the way.

First of all, the story only happens because George Bailey (Jimmy Stewart) no longer wishes to exist, and Clarence (Henry Travers) tries to talk him out of it by showing him what would happen if George never lived.

Or we can go even earlier than that. George is only on the bridge because a rich man, Mr. Potter (Lionel Barrymore), purposely concealed the whereabouts of a large missing sum of money. Potter knows it will destroy the Building and Loan and will likely get George sent to jail and does it for precisely that reason.

There’s also the pharmacist that kills a child accidentally. And George’s brother dying young without George to save him leads to several more American troops dying in World War II. Or, worst of all, George’s wife Mary (Donna Reed ends up a spinster AND a librarian! (GASP! HORROR!)

Still, that ending is so uplifting, you forget all about how dark it got before the dawn.

Image Credit: RKO Radio Pictures. 

Kiss Kiss Bang Bang

Kiss Kiss Bang Bang

Nearly any Shane Black film could be on this list—and there is, in fact, another on the way—as the man loves setting his movies at Christmas. However, KKBB stands out as easily the funniest and most fully realized of the bunch.

Harry Lockhart (Robert Downey Jr.) took a job as an actor after auditioning keeps him from being caught and arrested. On set, he’s paired with a private investigator “Gay” Perry (Val Kilmer), who’s going to help Lockhart seem plausible on-screen. Instead, they end up with a real, bloody mystery on their hands. Before long, Lockhart’s childhood crush Harmony (Michelle Monaghan), dressed as in a fetching Santa outfit, becomes entangled, too. As a result, several people end up dead, accusations of an incestuous affair hangover at least one person, and Lockhart loses a finger.

But it does it all laughing all the way (hohoho!) and finds a few happy endings in the debris.

Image Credit: Warner Bros. 

Long Kiss Goodnight

LongKissGoodnight

As promised, here’s your second Shane Black film, this one with just a script from him. Unlike many Black vehicles, the Christmas setting proves to be a bit more than just set dressing.

The holidays should be a festive time. However, for Samantha Caine (Geena Davis), this season feels… unusually complicated. After a car accident gives her a concussion, and she immediately kills a deer with her bare hands, she starts to feel like someone else.

Amidst the lights and tinsel, Samantha attempts to hash that out as government death squads suddenly seem to be everywhere she goes. She has to figure out who she is, why they all want her dead, how to find her kidnapped daughter, and how to save the Christmas Parade (yes, really).

Rarely does one have to fire so many bullets or use so much C4 in pursuit of a happy ending, but, hey, the holidays can be difficult.

Image Credit: New Line Cinema.

The Night Before

the Night Before

Three friends are bringing the curtain down on their traditional Christmas bacchanalia. For 14 years, Chris Roberts (Anthony Mackie) and Isaac Greenberg (Seth Rogen) have gotten together with childhood friend Ethan Miller (Joseph Gordon-Levitt) to distract him on his least favorite day. It began in 2001 when his parents died and provided them with years of wonderful memories. But times change. Isaac is about to be a dad, Chris is a professional football player, and Ethan seems as stuck in arrested development as ever.

Before they can bid the tradition adieu, however, they’ll need to consume significant amounts of drugs, have stress daydreams about their children becoming exotic dancers, start fights, attend and be tossed out of New York’s most exclusive Christmas party, and meet up repeatedly with the world’s most frightening drug dealer (Michael Shannon). Friendships fray, revelations revealed, public proposals facilitated by Miley Cyrus rejected.

Still, the film and the friends manage to discover a new path that finds a way to keep them together without substance abuse.

Image Credit: Sony Pictures Releasing. 

The Ref

the ref

First, yes, you will have to ignore the Kevin Spacey of it all. It’s excellent here, but if the man makes your skin crawl—and who could blame you—this is probably best to skip.

However, if you can separate the man from the role, The Ref is a bruisingly funny film about a WASP Christmas pushed to the brink by a thief and a marriage on the edge. Of all the films on this list, its ending is probably the gentlest. It does, admittedly, feel out of step with the rest of the film. It’s a bit too syrupy, considering the acid it spits from the start. However, it being Christmas and so darkly funny until then, one more easily forgives a too-happy ending. Especially given that it is a happy ending with several people still tied up in ribbon and wrapping paper for the sin of being annoying and being at the wrong family dinner at the wrong time.

Come for Dennis Leary at his most motormouthed while still feeling like a character, stay for Christine Baranski’s reading of the line, “Slipper socks, medium!”

Image Credit: Buena Vista Pictures.

Scrooged

Scrooged

While Ebenezer Scrooge is a cynical person in and of himself, an adaptation of A Christmas Carol that feels equal in cynicism is rare. Scrooged is that exception.

Part of it is undoubtedly the setting and the era. The business aspect of show business—specifically TV production here—tends towards fairly soulless depictions in most entertainment pieces. Even worse is the ’80s. Already a time that seemed cynical at the moment, it has only grown more so in the rearview.

Bill Murray’s performance as Scrooge helps too as, unlike many Ebenezers, he doesn’t shrink as the ghosts come into his life. Instead, he remains as spiteful as ever, even in the face of his fear, until the film’s final moments.

And for the most cynical interpretation of Christmas Carol, it only makes sense that it boasts the silliest sweetest ending, a sing-along with puppets and children!

Image Credit: Paramount Pictures.

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Did we miss a movie to bring a little darkness to the flickering electric candles? Is there a film that does cynical and sweet better than our selections? Let us know in the comments and on Twitter!

This post was produced and syndicated by Wealth of Geeks.

Image Credit: Elevation Pictures. 

Featured Image Credit: Columbia Pictures. 

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Tim Steven is a sad tomato, Tim Stevens is three miles of bad road. He’s also a therapist, staff writer and social media manager for The Spool, and a freelance writer with publications like ComicsVerse, Marvel.com, CC Magazine, and The New Paris Press. His work has been quoted in Psychology Today, The Atlantic, and MSN Ireland. Feel free to find him @UnGajje on Twitter or in a realm of pure imagination.