10 Movies I Demand You Watch This Holiday Season

Twas the weekend after Thanksgiving and all through the apartment, not a creature was stirring not even my sleeping cat. Oh, pish posh. This is just a fancy way to say I’m diving into the holiday season by binge watching a ton of made for TV movies on Hallmark and Lifetime channels with cheesy dialogue, fake snow, great tunes, and lots of heart. (I cry at 75 percent of them.) I love just about everything about this time of year but oh gosh, dusting off the DVDs we only watch in December is like Christmas morning all on its own. So today I wanted to share the top 10 movies you MUST WATCH to make the most of your holiday season. (No Hallmark or Lifetime movies included; sorry about that.)

Sidenote: these are in no particular order. I could never, ever do it!

1. Serendipity (2001): Kate Beckinsale and John Cusack bump into each other in a crowded Bloomingdales during the holiday season and both want to buy the last pair of leather gloves. They end up spending one night hanging out and totally connect but they are both taken by other people. Kate’s character proposes they leave their “relationship” to chance and allow the fates to bring them back together. This has been one of my favorite movies since I first saw it in theaters after a shift at CVS. There’s ice skating, Frozen hot chocolate, and lots of tubas. (Seriously.) Such a romantical flick.

Holiday song pick: “Cool Yule” by Louis Armstrong.

2. White Christmas (1954): You may need your tissues handy for this one. An entertainment duo head to a Vermont Inn during the holidays and end up scheming to save the place for their former commanding officer. There’s romance, some misunderstanding, and some beautiful performances from Bing Crosby, Danny Kate, Rosemary Clooney, and Vera-Ellen.

Holiday song pick: “Snow” by Irving Berlin.

3. Love Actually (2003): Does this movie need an introduction? Six couples around the holidays in various states of relationship: nonexistent, unrequited, complicated, very sad, exciting, and totally happy. I love the way these characters find themselves linked to one another, and how honest these storylines played out. Even though it’s a Christmas movie, not everyone gets their happy ending and year after year, I’m left to contemplate how it all goes down. It’s just excellent.

Holiday song pick: This soundtrack is ah-mazing but I’d say: “All Alone On Christmas” by Darlene Love.

4. The Muppet Christmas Carol (1992): This was the first Muppet film released after the death of creator Jim Henson, and it’s directed by his son, Brian. As my husband likes to remind me, the film is so closely resembles the Dickens tale mixed in with some wacky Muppet humor and memorable songs. The Muppet Christmas Carol has become part of our Christmas Eve tradition and it never, ever gets old.

Holiday song pick: The whole album is classic, but I love “It Feels Like Christmas” by Paul Williams.

5. The Santa Clause (1994): If there’s a movie that really makes me believe in the magic of Christmas, it’s this one. A divorced dad and his son rediscover their relationship in the strangest and most wonderful of ways: dad accidentally become the new Santa Claus. A trip to North Pole, lots of doubts, and so much wonder to be discovered. I basically tear up every time I watch. Real talk: I also love The Santa Clause 2 but I pretend the third doesn’t exist.

Holiday song pick: “Away to the Window” orchestration by Michael Convertino.

6. Elf (2003): Is there anyone who hasn’t seen this movie? I guess probably not. I could watch it so many times before Christmas, and it could never get old — so this one has to get a few viewings in every season. From the publishing plotline to the budding relationship between Buddy and his brother, the amazing Christmas decorations and NYC love, it’s just about perfect. (Universe, please don’t ever ruin it by doing a sequel.)

Holiday song pick: “Pennies From Heaven” by Louis Prima.

7. A Charlie Brown Christmas (1965): Christmas Time is Hereeee… I just realized I lied. This is the one MADE FOR TV flick pick I have on this list. Since I was a little girl, this movie has been a must during Christmas time. Against the perfect soundtrack, the Peanuts gang certainly teaches us the true meaning of Christmas.

Holiday song pick: “Linus & Lucy” by the Vince Guaraldi Trio.

8. Home Alone 2 (1992): Another childhood fav and the number #1 reason why I have always loved Christmas in New York. Kevin McAllister gets himself in a pickle yet again and mistakenly lands in New York when his family travels to Florida. (God, so much of this movie never happen now… including that heartbreaking Twin Tower scene early in the movie.) Kevin reunites with the bad guys from the first movie, and schemes to save the kids, his butt, and a really nice pigeon lady. Despite the questionable parenting in this movie, it’s so heartwarmingly great.

Holiday song pick: “Christmas All Over Again” by Tom Petty.

9. The Family Stone (2005): I warned you to grab the issues earlier but you might really want to listen to me for this one. Family reunion at Christmas time with new girlfriends and rivalries and some heartbreaking secrets and surprising switcheroos. This movie perfectly captures all the change that happens as we get older, and how holidays are destined to evolve — especially in ways we don’t want them too. GOD THIS MOVIE IS SO FREAKING GREAT.

Holiday song pick: “Have Yourself a Merry Little Christmas” by Judy Garland. (Meet Me in St. Louis isn’t on this list but it’s certainly a runner up for a different kind of holiday movie.)

10. Miracle on 34th Street (1947) or (1994): I’m all for original movies but this is one instance where it’s difficult for me to choose between the 1947 version and the 1994 one. Both are so amazing for different reasons, and it seems fitting to choose the 1947 film because Maureen O’Hara passed away this year. But it’s tough. I’m going to say this: I think Miracle on 34th Street does exactly what The Santa Clause does — makes people of all ages reevaluate their beliefs in magic and something more than we can see. It’s such a hopeful movie and I love how the big Thanksgiving Parade in NYC kicks off the film.

Holiday song pick: “Have Yourself a Merry Little Christmas” by Kenny G. (1994)

Now call me when you finish this task, and make sure you have plenty of candy canes and egg nog to keep you company. Happy holiday movie watching! Fa la la la laaaaa.

9 thoughts on “10 Movies I Demand You Watch This Holiday Season

  1. Tiff @ Mostly YA Lit says:

    Excellent picks! My faves from this list are Love Actually, Serendipity, and Home Alone 2. I feel like this says a lot about me – my love of London and New York, especially at the holidays.

    I have a real soft spot for the original Home Alone as well. I haven’t seen The Family Stone in awhile, I think I need to rewatch it.

    Other holiday movies I adore: The Holiday (actually I can’t believe this isn’t on your list! It’s the best!) and While You Were Sleeping. I also love watching the Roswell Christmas episodes because they’re SO good.

  2. Alexa S. says:

    I love this post, E!! My favorite of all the movies you’ve mentioned is Love Actually. I watch that one constantly, at any time of year. It’s almost like comfort food in movie form, now that I think about it 😉

  3. Holly J says:

    Ah, quite a few of my faves are on this list! I LOVE the Home Alone movies (except the 4th, I think? Let’s pretend that one never happened). No matter how many times I’ve seen them, especially the New York one (which is my favorite too!), they always make me laugh. I also looove Elf. I mean, who doesn’t? Oh, and A Charlie Brown Christmas! I haven’t seen Love, Actually, but I really want to. And I think I’ve seen Serendipity, but it was a LONG time ago and I don’t remember much about it. But I love Christmas movies and will definitely have to check some of these out.

    Great post! 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *