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The 12 Most Entertaining Holiday Films of All Time

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Eyes Wide Shut (Getty Images)
Eyes Wide Shut (Getty Images)

 

Chances are, in the next month you’re going to be with a group of people who want to watch a holiday movie. But that doesn’t mean you have to queue up Miracle on 34th Street. (Or worse, The Santa Clause.)

Instead, you should settle in by the fire with one of these—our picks for the 12 most entertaining holiday films of all time. Sure, they have a Yuletide vibe (some stronger than others). But they’ve also got something that’s missing from the likes of Jingle All the Way: attitude.

Bad Santa (Columbia Pictures)
Bad Santa (Columbia Pictures)

 

12. Bad Santa (2003)
Watching Billy Bob Thornton swill booze and yell at kids while wearing a Santa costume somehow never gets old. It’s also a pleasure to watch both John Ritter and Bernie Mac, two fine actors who are sadly no longer with us.

11. Trading Places (1983)
An ’80s take on Mark Twain’s The Prince and the Pauper, Trading Places showcases Eddie Murphy and Dan Aykroyd at the height of their comedic powers. Interestingly, in Italy the movie has become a Christmas classic; it’s broadcast every year, usually on December 24.

10. Pieces of April (2003)
Shot for a mere $100,000, Pieces features a twenty-something, pre-Tom Cruise Katie Holmes trying to make Thanksgiving dinner for her family in a tiny New York City apartment without a working oven. Sound boring? The New York Times disagreed, calling it “an intelligent and touching farce.”

Elf (New Line Cinema)
Elf (New Line Cinema)

 

9. Scrooged (1988)
Your enjoyment of this film (an update of Charles Dickens’ A Christmas Carol) greatly depends on how much you enjoy Bill Murray. If you (like most logical human beings) are a fan, then, to borrow a line from the film, “Yule love it!”

8. Elf (2003)
Nobody plays an orphan who thinks he’s one of Santa’s elves better than Will Ferrell, and Elf, while not exactly packing “attitude,” offers plenty of laughs to go with its Christmas cheer and family-ness. Also, Peter Dinklage as a best-selling children’s author is priceless.

7. A Very Harold & Kumar 3D Christmas (2011)
This is easily the best three-dimensional stoner comedy Christmas movie in the history of cinema. And while it’s all pretty silly, there are some important themes here. Namely: reconnecting with old friends and standing up to in-laws.

The Apartment (Getty Images)
The Apartment (Getty Images)

 

6. National Lampoon’s Christmas Vacation (1989)
This is arguably Chevy Chase’s last movie before he got unfunny, and Randy Quaid is a tour de force as the turtleneck dickey-wearing Eddie. Look closely to spot a pre-Big Bang Theory Johnny Galecki and a pre-Seinfeld Julia Louis-Dreyfus.

5. Gremlins (1984)
Talk about a misunderstood picture. It’s known as a Spielberg movie, although he served as executive producer, not director. (It was directed by Joe Dante and written by future Home Alone helmer Chris Columbus.) It’s also thought to be a kid’s film, but it’s loaded with black comedy elements.

Gremlins are blown up in a microwave and a movie theater, and the main character’s girlfriend (Phoebe Cates) hates Christmas because her father died in a chimney while dressed as Santa Claus. Dark stuff indeed. No wonder the MPAA created the PG-13 rating as a reaction to this film.

4. Lethal Weapon (1987)
This is probably the best buddy cop film ever, but it’s also very much a holiday movie. There’s a chase down Hollywood Boulevard on Christmas Eve, a shootout at a Christmas tree farm, and it ends (spoiler alert) with Riggs spending Christmas with Murtaugh and his family. Plus, the whole thing starts with “Jingle Bell Rock.”

Eyes Wide Shut (Getty Images)
Eyes Wide Shut (Getty Images)

 

3. The Apartment (1960)
First of all, without this Billy Wilder film, there would be no Mad Men. Also, it’s got the greatest holiday office party scene in cinematic history. Then there’s the supremely charming Jack Lemmon, everyman-ing it up opposite Shirley MacLaine (at her most adorable). Fred MacMurray as the dirtbag boss is the icing on it, cake-wise.

2. Eyes Wide Shut (1999)
Stanley Kubrick’s last movie, Eyes Wide Shut holds the Guinness World Record for the longest continuous film shoot period (more than 15 months). The novella on which it was based, Dream Story, was set during Mardi Gras (in Vienna), but Kubrick changed it to Christmas (in New York). The switch works perfectly.

Alonso Duralde, in his book Have Yourself a Movie Little Christmas, calls the erotic drama a “Christmas movie for grownups.” And critic Lee Siegel suggests that the film’s recurring motif is the Christmas tree, writing, “Desire is like Christmas: It always promises more than it delivers.”

Die Hard (Getty Images)
Die Hard (Getty Images)

 

1. Die Hard (1988)
Made for $28 million, Die Hard grossed more than $140 million theatrically, turned Bruce Willis into an action star, spawned four sequels, and is considered one of the best action movies ever made, as well as one of the greatest films ever made.

But people don’t really think of it as a holiday movie. Well, they should. The entire story takes place on Christmas Eve, and Hans Gruber and his henchmen seize the Nakatomi Tower during the company Christmas party.

What’s more, the score features sleigh bells and “Winter Wonderland,” and the end credits begin with “Let It Snow.” Yippee-ki-yay? Sure. But also: Ho-ho-ho!

—Shawn Donnelly for RealClearLife