There’s just something about holiday movies. They’re like holiday music. After about 10 minutes, you’ve had enough for the whole year already and you have a weird urge to shove that candy cane you’ve licked into a sharp point right into your ear.
The movies on this list turn the holidays into more of an adventure than an endurance contest. They are, mostly, light on the ultrasaccharine Hallmark stuff that’s usually packed into flicks about Thanksgiving, Christmas, and New Year’s Eve. There are even a couple on here that you’ll be able to enjoy with the kids, without any significant mental scarring. And no, Die Hard is not on this list. You should be watching that every year. On Christmas Eve. Every year. That’s a given.
10. You’ll Get Nothing and Like It!: Jingle All the Way (1996)
Directed by: Brian Levant
Starring: Arnold Schwarzenegger, Sinbad, Rita Wilson, Phil Hartman
Yes, it’s an Arnold movie, but it’s family-friendly 1990s Arnold, so it’s cool for the kiddies. The action star plays a slightly irrational workaholic dad who is desperately trying to prove to his wife and son that he really does give a shit about them at Christmas, only to find out right before the holiday that he already screwed the pooch weeks earlier by not preordering the only gift his son asked for that year: the ultra-popular Turbo Man. His quest for a last-minute doll takes him all over town, and pits him against another dad on a similar quest, played by … Sinbad? Yeah, it’s Sinbad, as a deranged postal worker. (Don’t you miss the ’90s?) This movie has it all. Sinbad trying to blow up a radio station and almost killing multiple people at a parade for a toy doll? Check. Arnold viciously battling a gang of price-gouging scumbag Santas? Yep.
Adventure Advice: If your wife doesn’t recognize you from 3 feet away because you have a piece of transparent orange-tinted plastic over your eyes — or from your very distinctive Austrian accent — your marriage is already doomed.
9. It’s Like, Christmas, Man: A Very Harold and Kumar 3D Christmas (2011)
Directed by: Todd Strauss-Schulson
Starring: Kal Penn, John Cho, Danny Trejo, Elias Koteas
Naturally, the third installment in this juvenile stoner comedy film series is a Christmas movie. Why not? The strange thing is, it really works, and this one is better than the previous two movies. It’s a little less raunchy, and it actually has some heart, which was all kinds of necessary, since the stars are no longer in their very early 20s. Harold and Kumar had to grow up eventually. We find the stoner duo and roommates are now estranged, and have been for some time. Harold (Cho) has quit smoking pot, got a high-paying job, got married, and is trying to start a family while desperately trying to impress his super judgmental father-in-law (Trejo). Kumar (Penn) hasn’t really changed. Naturally, he shows up at Harold’s house and everything goes to hell, setting the reluctantly reunited friends on an all-night Christmas Eve quest. The whole movie is worth it just for the “I shot Santa Claus in the fucking face. He’s real, and I shot him in the face” scene.The 3D stuff feels super stale and obvious, but hey, Santa gets shot in the face.
Adventure Advice: When flying your sleigh over the Northeast, beware of random shotgun blasts from the North Jersey area. Or maybe armor your sleigh.
8. The One with Everyone in It You Probably Haven’t Seen: 200 Cigarettes (1999)
Directed by: Risa Bramon Garcia
Starring: Ben Affleck, Casey Affleck, Dave Chappelle, Paul Rudd, Kate Hudson, Jay Mohr, Christina Ricci, Courtney Love, Elvis Costello
This movie has a late ’90s charm that is undeniable, though it’s set in 1981. It also has a cast full of today’s famous faces in their younger forms. Several characters on a variety of New Year’s Eve missions ultimately converge in unexpected ways at a New York City post-midnight house party, and they all figure things out about themselves along the way. And that’s what the movie’s about: getting to the party. Or killing time so you don’t show up too early. There’s a lot of ’90s angst and melodrama, but there’s general hilarity and it’s not heavy in any way, making it perfect for that mental twilight of the morning after a New Year’s Eve party. And if you don’t feel a deep tugging sadness for Monica — the woman who plans an elaborate party, thinks nobody is going to show up when midnight comes and goes, drinks herself into a blackout, only to find out everyone eventually did show up, even Elvis Costello, and she slept through it all — then you’re a bad person. Oh, and since nobody smokes anymore, the title is a reference to how many cigarettes come in a carton.
Adventure Advice: Never, ever kick it into fifth too early in the night, especially when it’s your party.
7. A Better Christmas Carol: Scrooged (1988)
Directed by: Richard Donner
Starring: Bill Murray, Karen Allen, Bobcat Goldthwait
A Christmas Carol is the original holiday adventure story from Charles Dickens penned in 1843, which has been adapted countless times in movies and on TV, but this version isn’t quite like any other before or since. It reimagines the story’s protagonist as a TV executive named Frank Cross (Murray). He’s a high-powered ’80s stereotype of a shrewd, heartless businessman who has no personal life, lives at the office, drinks vodka and Tab, and has a giant dictionary definition painted on his office bathroom wall that reads “Cross: A thing they nail people to.” He goes through the classic visitation of three spirits who attempt to teach him morality lessons by showing him things from his past and future that will, hopefully, inspire him to change his shitty ways. Each visit was updated in a manner that, wisely, doesn’t make them too dated over three decades later. The film’s got heart, but it’s not nearly as sappy as many direct adaptations of this old story, and it manages to stay just faithful enough to the original structure and characters that nothing is lost. Plus, Bobcat Goldthwait goes on a shotgun rampage and Santa defends his toy shop with an M16A2. The ’80s weren’t so bad after all.
Adventure Advice: The scary, mute ghost who literally looks like the grim reaper is gonna show you some scary-ass shit. Brace yourself with an extra vodka and Tab on the rocks.
6. When Toys Come to Life … and Die: The Christmas Toy (1986)
Directed by: Eric Till
Starring: Dave Goelz, Steve Whitmire, Kathryn Mullen
This is a pure Jim Henson Christmas classic, complete with an intro from Kermit the Frog himself rocking a Santa suit. A playroom full of toys belonging to a brother and sister come to life when they’re left alone at night, revealing a whole little secret society of their own. Sound familiar? Yeah, it’s Toy Story, but nine years earlier and with puppets who mostly have childlike personalities. Like most things made for kids in the ’80s, there’s a really creepy darkness behind it all. If the toys don’t return to the exact positions in which they were last left by humans, they fucking die. If they get caught where they shouldn’t be, they fucking die, and get dumped in a pile of other dead toys. Yeah. So, follow these wholesome, singing Muppets on a life-and-death Christmas Eve journey down to this year’s tree to meet the newest addition to the playroom, and find out who doesn’t make it to see Christmas morning.
Adventure Advice: The concept of toys coming to life when people aren’t around is terrifying. Don’t trust your toys.
5. An Anti-Family Christmas Odyssey: Go (1999)
Directed by: Doug Liman
Starring: Sarah Polley, Katie Holmes, Timothy Olyphant
This is one of the better movies with a multi-storyline format that bites off the structure of Pulp Fiction. There’s no eggnog or warm fuzzy moments in this drug-fueled odyssey that chronicles the weekend-before-Christmas antics of a group of early-20-somethings who work together in a Los Angeles supermarket. As their stories diverge and intersect, they make a long series of really bad choices that result in them dodging drug dealers, undercover cops-slash-Amway pushers, two informant soap opera stars caught in a love triangle, and armed strip-club owners with a grudge. This movie is funny as balls, and, for anyone who was young in the late ’90s, it serves as a neat time capsule from the days when raves were a thing and Timothy Olyphant had yet to don a cowboy hat. His severe and pointy sideburns alone make this one worth a watch.
Adventure Advice: Selling dumbass ravers aspirin and OTC allergy meds as designer drugs for ridiculous prices at a Christmas-themed rave sounds like a good way to get quick rent money. Wait, no it doesn’t. Don’t do that.
4. ’Tis the Season To Beat the Shit Out of Dead Cows: Rocky (1976)
Directed by: John G. Avildsen
Starring: Sylvester Stallone, Talia Shire, Carl Weathers, Burt Young
While Rocky is categorized as an Oscar-winning sports movie, the holiday season serves as a backdrop for the entire film. It’s actually one of the few movies that hits Thanksgiving, Christmas, and New Year’s Day. (The Creed vs. Balboa fight is held on New Year’s Day, 1976.) While the action stays in Philly, the journey traveled by small-time club fighter Rocky Balboa (Stallone) during the six-week holiday season is completely transformative. He starts off fighting in a dingy club, where he gets $40.55 if he wins and starts smoking a cigarette as soon as he gets out of the ring. By the end, his name is known all over the world and he can sprint for at least 6 miles and fly up the Philadelphia Art Museum steps to top it off. He then proceeds to give the heavyweight champion of the world the fight of his life — all because he had a rhyming nickname Apollo Creed (Weathers) thought was cool. If the scene where drunk-ass Paulie is swinging a baseball bat around the living room with a holly wreath dangling from his arm, breaking lamps and shit while ranting about what he could have made of his life before questioning his adult sister’s virginity, doesn’t put you in the holiday spirit, nothing will.
Adventure Advice: If your fighting strategy against a Muhammad Ali-like champion boxer is to use your face and head to block most of his punches, you’re gonna come out lookin’ different. Just so you know.
3. Beard Salmon? Yum!: Trading Places (1983)
Directed by: John Landis
Starring: Eddie Murphy, Dan Aykroyd, Jamie Lee Curtis
The cast of this all-time classic includes some of the best comedic actors of a generation at their peak, and almost 40 years later, it’s still goddamn hilarious. And, being another movie that isn’t specifically about the holidays, but rather has a plot that runs through them, it shows us what Christmas looked like in Philadelphia circa 1983. This life-swapping “Prince and the Pauper” tale about old crusty rich white dudes being awful and manipulating peoples’ lives over a $1 bet, and getting some intense financial justice for it in the end, begins some time just after Thanksgiving and runs into the first few days of the New Year. Many a kid who saw this in the ’80s grew up disappointed to find out there are, in fact, no raucous New Year’s Eve costume parties held on all-night Amtrak train routes. Hollywood is such bullshit. And if anyone tells you they understand what’s going on in the trading room floor scene at the end, they’re a damn liar.
Adventure Advice: You mess with the ape, you get the … well, you get banged by that ape, that’s what happens.
2. Thieving All the Way: Bad Santa (2003)
Directed by: Terry Zwigoff
Starring: Billy Bob Thornton, Tony Cox, Bernie Mac, John Ritter
This super R-rated heist story isn’t only set against Christmas in a suburban Arizona mall, but it’s deeply tied to one of the symbols of the holiday itself. Willie (Thornton) is a straight-up alcoholic — the pissing himself at work and puking in an alley on Christmas Eve alone kind of alcoholic. He’s also a petty crook and an all-around piece of shit, and he knows it. How has he managed to stay alive and in booze the past few years? He came up with a scheme that involves him working as a mall Santa in one state or another for the holiday season. His partner, Marcus, a little person, works as an elf and Willie’s wrangler. When the mall is bursting with cash on Christmas Eve, they stick around after closing. Willie cracks the mall’s safe while Marcus disables the security system and steals high-end merchandise. It works for a few Christmases, until Willie’s drinking gets more out of control than usual on this most recent job, and he meets a young, goofy kid who forces him to grow something akin to a conscience. Watch the uncut version, Badder Santa. It’s dirtier. And whatever you do, DO NOT watch the sequel.
Adventure Advice: “Shit happens when you party naked.” Truth.
1. “Just Rent a Car and Drive It, Bro”: Planes, Trains and Automobiles (1987)
Directed by: John Hughes
Starring: Steve Martin, John Candy
One cannot truly appreciate every hilarious facet of this movie until one has a job that requires a good amount of travel. Racing to get home in time for the holidays from a place you didn’t want to be in the first place — in this case, for Thanksgiving, with home being Chicago and the place being New York City — isn’t an untrodden concept in Hollywood, but Planes, Trains and Automobiles did it best. And this kind of shit happens, or did, in the before times where COVID didn’t have everyone scared to leave their house. Ask anyone who has wound up driving a rental car for three days, sleeping on the shoulder of the highway, instead of waiting at the airport for about the same amount of time on standby to catch a plane home. The struggle is real, or was. Ever have trouble at the airport rental car counter or get abandoned by the shuttle in that giant fuck-off parking lot with a ton of baggage? I miss those days, too. In case you wanted to know, in the rental counter scene, the word “fuck” is used 18 times in 40 seconds. That’s pretty solid for a holiday movie.
Adventure Advice: Ever take your wallet out of your pocket and put it in the glove compartment, or center console, or on the dashboard of a car? Don’t do that. Keep it in your pants.