7 Christmas Movies That Aged Poorly Ranked From Mildly Cringey to Unwatchable

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Ah, the holiday season! A time for cozy blankets, hot cocoa, and, of course, a marathon of Christmas movies. But not every film stands the test of time. Some can turn a festive mood into a cringe-fest faster than you can say “Christmas cheer.” So, grab a mug of your favorite drink and let’s take a lighthearted stroll down memory lane, ranking seven Christmas movies that didn’t quite age like fine wine. Think of this as your friendly guide to avoiding holiday movie disasters!

a house with a lot of snow on the ground
Photo by Ana Petrenko

1. Home Alone 2: Lost in New York (1992)

Ah, the beloved “Home Alone 2.” While the original is a holiday staple, the sequel is a mixed bag. Kevin McCallister is back, but this time in the Big Apple, with all the hilarity and chaos that ensues. However, watching it now, it feels a bit too much like a rehash of the first one—like they just slapped on a new setting without bringing anything fresh to the table. Plus, the whole concept of a kid wandering around New York City alone? Yikes! It’s mildly cringey to think about its implications. But hey, if you’re in the mood for some nostalgia, go ahead and enjoy it!

2. The Santa Clause (1994)

Next up, we have “The Santa Clause.” Tim Allen turning into Santa after an unfortunate incident is a wild ride, and it’s packed with laughs—at least it was back in the day. But let’s face it, the humor hasn’t aged gracefully. The idea of a guy falling into the role of Santa because of a freak accident feels outdated. And don’t even get me started on the portrayal of the elves. It’s hard to ignore the cringe factor when you realize how many questionable jokes and situations there are. Still, it’s got that charm that makes it hard to completely write off.

3. Jingle All the Way (1996)

Starting off our list is the classic, or perhaps not-so-classic, “Jingle All the Way.” Arnold Schwarzenegger as a dad on a desperate quest for a toy? It’s got potential, right? But watching it now, you can’t help but chuckle at how over-the-top everything is, from the ridiculous action sequences to the lovable yet utterly absurd premise. It’s mildly cringey but still kind of fun if you’re in the right mood. I mean, who doesn’t love a good dose of nostalgia mixed with a sprinkle of “what were they thinking?”

4. Santa’s Slay (2005)

Okay, let’s get a little darker with “Santa’s Slay.” It’s a horror-comedy that takes the jolly old man and turns him into a murderous villain. While it was probably meant to be a tongue-in-cheek take on Christmas, the execution leaves much to be desired. The jokes can be painfully bad, and the gore seems unnecessary. It’s the kind of movie you might throw on for a laugh with friends, but you’ll probably spend more time cringing than enjoying it. It’s like a car accident you can’t look away from.

5. The Holiday (2006)

Now, “The Holiday” has its fans, and I get it. It’s a rom-com set against a holiday backdrop, starring big names like Kate Winslet and Cameron Diaz. But let’s be real: it’s a bit of a mess. The film’s premise is charming, but the execution feels dated, with its over-the-top romantic tropes and predictable plot. Plus, watching it now, you might find yourself cringing at some of the clichés that were once considered cute but are now just… well, tired. It’s not unwatchable, but you might find yourself laughing at the wrong moments.

6. The Holiday (2006)

Now, “The Holiday” has its fans, and I get it. It’s a rom-com set against a holiday backdrop, starring big names like Kate Winslet and Cameron Diaz. But let’s be real: it’s a bit of a mess. The film’s premise is charming, but the execution feels dated, with its over-the-top romantic tropes and predictable plot. Plus, watching it now, you might find yourself cringing at some of the clichés that were once considered cute but are now just… well, tired. It’s not unwatchable, but you might find yourself laughing at the wrong moments.

7. Four Christmases (2008)

“Four Christmases” is the kind of film that had its moments upon release, but now? It’s just awkward. Vince Vaughn and Reese Witherspoon try to navigate the holiday chaos of visiting four different families in one day, but it often feels forced and uncomfortable. The humor leans heavily on stereotypes and misunderstandings that just don’t hit the mark anymore. It’s like watching a train wreck—you can’t look away, but you’re cringing the whole time. If you’re in a particularly forgiving mood, you might still chuckle, but be prepared for some eye-rolls.

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