Much like the holiday season, the 1990s were a magical time. America's budget was balanced. Sir Mix-A-Lot was a famous person. So much happened.
Unsurprisingly, the 10-year span yielded pieces of pop culture that are totally bonkers, often beautiful, and, more than anything else, so utterly '90s. In that spirit, here are the hands-down best holiday movies from the decade that gave us Beanie Babies, Free Willy, and The Macarena — things that don't make a whole lot of sense in retrospect, but hold a special place in our nostalgic hearts nonetheless.
The Nightmare Before Christmas
Put holiday claymation in the hands of macabre master Tim Burton, and you get hybrid Halloween-Christmas characters that are creepier than Krampus. It's not mandatory for Jack "The Pumpkin King" Skellington and Sally fans to wear hoodies and black-and-white stripe witch pantyhose. You are more than welcome to do that, but proving your fandom by knowing all the words to "This is Halloween" is also completely acceptable.
The Muppet Christmas Carol
Michael Caine's Ebenezer Scrooge is our all-time favorite. And having the Muppet crew at his side only makes us love this Christmas Carol more. Gonzo serves as the narrator, Charles Dickens, while Kermit and Piggy take on Bob and Emily Cratchit, and Statler and Waldorf portray the musical ghosts of Jacob and Robert Marley. It's funny, it's touching, and it makes us cry every single time. "When Love is Gone"? Total tearjerker. That's not to mention we get choked up just thinking about how The Muppet Carol is the first Jim Henson Productions film released after both its namesake and puppeteer Richard Hunt passed away. It's dedicated to their memory.
Home Alone 2: Lost in New York
Fairly superior to its predecessor, Home Alone 2 once again finds Macaulay Culkin abandoned by his family. (Think about how much therapy grown-up Kevin will require.) But this time around, he gets to chill at The Plaza, fraternize with Pigeon Lady, and save Duncan's Toy Chest from being robbed by fresh-outta-jail bad guys Harry and Marv, a.k.a. the sticky bandits, formerly known as the wet bandits.
You've Got Mail
We're not saying You've Got Mail is a better rom-com than Sleepless in Seattle, but You've Got Mail might be a better rom-com than Sleepless in Seattle. Meg Ryan and Tom Hanks square off as adversaries that fall in love via AOL e-mails. The pair are dueling bookstore owners. Ryan runs an indie children's shop that's shut down by Hanks' Borders-style literary mega-mart. Their online chemistry is stellar, and eventually the two can't help but meet IRL. Parker Posey and Greg Kinnear bolster the film's stellar cast, which also includes Jean Stapleton and Dave Chappelle.
Jingle All The Way
Howard (Arnold Schwarzenegger) is a crap dad who forgets to buy his son's Christmas present, an action figure called Turbo-Man. This is after he misses his kid's karate graduation. So he's already on thin ice, family-wise. We are to believe Turbo-Man, or, as Sinbad's character Myron calls him, "Turtle-Man," is the coolest toy that all the kids want, and is thereby virtually impossible to find. He searches for the Turbo-Man, yells at Phil Hartman about cookies, and, ultimately, becomes Turbo-Man.
I'll Be Home for Christmas
JTT plays a total douchebag who wants to ditch his fam and take his girlf, played by Jessica Biel, to the beach for Christmas. His plans change (for totally selfish reasons) and he has to get home for Christmas Eve dinner. During his cross-country travels, he doesn't really learn the meaning of Christmas, but he does get the proverbial shit kicked out of him via hitchhiking, buzzards, and not having anything to wear, save a Santa suit.
While You Were Sleeping
Sandra Bullock spends her life sitting in a tollbooth "like a veal." That is, until she saves her dream dude's life when he almost gets run over by a train. (Fun fact: Our little sister used to call this movie Man Got Run Over by a Train.) Dream guy Peter (Peter Gallagher) goes into a coma. Because Bullock's Lucy is totally alone in the world, she is mistaken for and proceeds to pose as his fiancee — even though they've never even met. Seems like this sad lady's scheme probably won't work out, right? Spoiler alert: It totally works out, but, in rom-com style, not quite how she expected.
Miracle on 34th Street
Honestly, it's just easier to watch the Matilda-starring 34th Street, because we don't get preoccupied with how Christopher Walken totally knows what happened on that boat.
The Santa Clause
Kind of the Mrs. Doubtfire of holiday movies, The Santa Clause finds Scott Calvin (Tim Allen) signing up to be the new Santa after the old one falls of his roof. His kid, Charlie, starts telling everyone that his dad is Santa, because he thinks it's super cool. His mom's new boyfriend (Judge Reinhold) is pretty sure that both Scott and Charlie are disturbed. Turns out, he's just disillusioned, wears terrible sweaters, and never got that Oscar Mayer weenie whistle he asked for.
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