The Art of Having Fun

Shades of Gray: Shades of Gray: My Favorite Holiday Flicks to Watch This Winter

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7 years ago

Each holiday season, I love to kick back, curl up on the couch, and turn on a few of my favorite holiday flicks to unwind. It’s such a fun time of year to pull out all those movies that you haven’t seen all year long, and have a little holiday movie marathon with your S/O, some friends, or even for a little quality time with yourself! I don’t know about you, but I’ll definitely be whipping up a batch of homemade hot chocolate, sitting by the tree, and indulging in a few of my holiday guilty pleasures. So whether you’re one to binge watch holiday movies or not (but really, who isn’t?), I’d venture to say that these Christmas favorites are ones that can easily be watched on repeat, holiday season or not. If you need a little help rounding out your movie playlist, keep scrolling to see my top 10 recommendations to watch this winter. I hope you love them as much as I do…

1. LAST HOLIDAY

Gray Malin's Favorite Movies to Watch This Winter - Last Holiday

Last Holiday is hands down one of my favorite movies, not just for the holidays, but of all time. (I even themed my 30th birthday party after it!) Queen Latifah is so fantastic to watch, and I love the message of the movie—that life is really all about the experience, and to live life to the fullest. It always makes me feel so good to give this movie a watch, and I can’t resist putting it on at least once (or a few times) every holiday season.

2. HOME ALONE 1 + 2

Gray's favorite winter movies - Home Alone

It’s no secret that Home Alone is a classic when it comes to holiday movies. The premise of a little kid accidentally left at home during the holidays, then subsequently having to defend his home from robbers is hilarious. Not to mention just all around entertaining. I don’t know about you guys, but I can’t let a Christmas pass without watching either the original or the Home Alone sequel at least once.

3. THE POLAR EXPRESS

The best movies to watch this winter, according to Gray Malin

The Polar Express is another one of those feel-good movies, that truly just embodies the feeling of Christmas. Plus, it’s fulfills every childhood dream to take a trip to the North Pole, and teaches the most heartfelt lessons along the way. If that doesn’t make for the perfect holiday movie, I don’t know what does.

4. THE HOLIDAY

The best Christmas movies, according to Gray Malin

For all you hopeless romantics who can’t stay away from a classic Rom-Com (guilty), The Holiday is a must-see. I can’t help but put this one on every year when winter rolls around, and for good reason. It’s such a feel-good movie, and with such a star-studded cast, can you really resist? The relationships and stories are so charming, it’s just about everything you could ask for in a holiday movie!

5. LOVE ACTUALLY

The best flicks to watch this winter, according to Gray Malin

Of course I’ve got another romantic comedy up my sleeve (and a few more coming later!). Love Actually is a classic, and it’s so fun to watch all the interrelated relationships of the many characters during Christmastime. Featuring a cast of several top British actors and telling the stories of the inevitable ups and downs of love, this holiday flick is a delight to watch, to say the least.

6. ELF

the best movies to watch this season, according to Gray Malin

As far as holiday comedies go, Elf is one that could easily take the cake. Will Ferrell is known to be a comedian, but his childish and naïve charm in this flick reminds me perfectly of the way a child sees everything during Christmas as pure magic. As a human elf thrown back into the real world, Elf is a sure way to get a laugh out of me over the holidays and, of course, ends with the cutest romance.

7. JUST FRIENDS

Gray Malin's favorite movies to watch during the winter - Just Friends

Speaking of holiday comedies… here’s another favorite! Just Friends tells the ultimate (and hilarious) story of getting out of the dreaded friend-zone. Almost everyone can relate to having that first hometown love, and this movie tells that struggle-to-win-their-heart in the funniest way. If you like romantic comedies that err more on the “comedy” side, this one is for you.

8. WHILE YOU WERE SLEEPING

Gray Malin's Favorite Holiday Movies - While You Were Sleeping

Who can resist an early Sandra Bullock movie? While You Were Sleeping is the classic story of crushing on that person who doesn’t know you exist, but this time with a surprising twist! Not only is it lighthearted and funny, but this romantic comedy also ends in the most heartwarming way. I can’t help but smile watching this love story, and I’m sure you will too.

9. THE SANTA CLAUSE

The Santa Clause - Gray Malin's favorite holiday movies to watch during the winter

I always love a good Disney movie, and there’s nothing funnier than a man who accidentally becomes Santa Claus. This one is another classic, and makes the idea of the real, down-to-earth Santa Claus come to life. If you want the definition of a Christmas comedy, you’ll have to give The Santa Clause a watch.

10. HOW THE GRINCH STOLE CHRISTMAS

Movies to add to your holiday watch list - How The Grinch Stole Christmas

Ah, the classic story of The Grinch. This Dr. Seuss story come to life is a Christmas must, and tells the heartwarming story of how The Grinch actually stole Christmas in Whoville (and his subsequent change of heart). Although in the movie The Grinch is bent on ruining the holidays, I think it’s safe to say that this movie does exactly the opposite! I hope these suggestions give you all a few ideas to add to your holiday binge-watching queue – I know I’ll have quite the list to watch this season! Do you have any holiday favorites I missed on this list?

Xx

GM

Photos: imdb.com