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Do you believe in fate? Or the success of really cheesy romantic comedies? This John Cusack vehicle takes place in New York around holiday time, which qualifies it as a Christmas movie. Cusack meets adorable Kate Beckinsale while holiday shopping — they both reach for the same pair gloves. Romance follows, only it gets complicated when Beckinsale decides to leave everything to fate. There's ice-skating in the snow, there's romance, there's John Cusack, there's the actual restaurant Serendipity! For Cusack fans, it's an absolute holiday must-watch.
How The Grinch Stole Christmas (1966)
Starring: Boris Karloff
Before Jim Carrey took his turn at the mean green Christmas-hating man, there was the animated film. Replete with hand-drawn animation and a downright adorable Cindy Lou Who (no Taylor Momsen to be found here), the 90-minute movie is pure charm. You can't watch this movie and NOT love Christmas. That's kind of the point. From the moment you hear the Whos sing "da-foo-do-ray," you'll be in full Christmas mode.
Meet Me In St. Louis (1944)
Starring: Judy Garland, Margaret O'Brien, Mary Astor
It's not Christmas until you watch Judy warble out the notes of "Have Yourself A Merry Little Christmas" in the snow. The movie is ostensibly about a family's move to New York City, but it contains a song about Christmas, ergo: it's a holiday movie. Garland also sings "The Trolley Song," which is low-key the catchiest song from a movie musical.
A Diva's Christmas Carol (2000)
Starring: Vanessa Williams, Kathy Griffin
You recall A Christmas Carol, the classic Dickens tale of holiday regrets. This movie takes that story and adds Vanessa Williams and Kathy Griffin to the mix. Vanessa Williams is the Diva in question. She plays Ebony Scrooge, "pop music's biggest diva." Griffin plays the various ghosts of Christmas in the movie that is leagues (upon leagues) better than Jim Carrey's 2009 iteration of A Christmas Carol.
The Family Stone (2005)
Starring: Sarah Jessica Parker, Dermot Mulroney, Luke Wilson, Rachel McAdams, Craig T. Nelson, Diane Keaton
This tale of home-for-the-holidays bickering is elevated by an all-star cast. Sarah Jessica Parker is perfectly wooden as Meredith, the one non-family member who attends the Christmas celebration. It's all familiar territory: Family secrets are revealed, someone ruins a precious holiday dish, and there are turtlenecks a-plenty. The real draw here are Craig T. Nelson and Diane Keaton, the respective Stone patriarch and matriarch. Family drama is what these actors do best, and the pair do not disappoint.