Our Team's 15 Favorite Holiday Movies

By Jason Freely / 6 months ago
Our Team's 15 Favorite Holiday Movies
Photo by Melissa Oholendt for Wit & Delight

We’re in the midst of the holiday season and I don’t know about you, but to us here at W&D, things feel as busy as ever. There are last-minute gifts to buy, presents to wrap, work deadlines to meet, gatherings to attend. Plenty of these things are very, very good, to be sure, but we’re human and we’re allowed to be both stressed and excited all at once.

One of the things our team is collectively planning to do (or is already doing…) as a means of relaxation is sitting back and watching a few of our favorite holiday movies. Today we’re rounding up each of our top movies to watch with family and friends as the snow falls outside, (preferably) with fireplaces all aglow.

After you read our picks, please do share your favorite movies with us in the comments! Seriously. I’m always on the hunt for new entertainment options, and I’d love to hear what gems of movies (or TV show episodes!) bring you particular joy this time of year.

Bridgette Dutkowski

Brand Director


1. Scrooged – I’m a HUGE Bill Murray fan (really, who isn’t?) and I have fond memories of watching this with my parents during the holidays. It’s a (very) 80s retelling of A Christmas Carol with Bill Murray playing Scrooge. It’s funny, lighthearted, and doesn’t take itself too seriously, which is my kind of holiday movie. 

2. Rudolph the Red-Nosed Reindeer – Having kids makes the holidays brand new again, and we dug up this gem not too long ago for our own kids to watch. Some of it hasn’t aged well (dad encouraging Rudolph to hide his nose—felt off to me). Aside from that, the kids love the story, and my husband and I love noticing how weird claymation actually is. 

3. Die Hard – My husband and I have jumped on the bandwagon of watching Die Hard during Christmas. I’m not sure how this tradition started, but after the kids go to bed, we make a gin & tonic and watch Bruce Willis in what is, probably, his finest role. 

Zoe Vossen

Fulfillment Manager – Shop Wit & Delight


1. Elf, hands down – My favorite scene is when Mr. Narwal says, “Bye Buddy, hope you find your dad!” It’s so sweet and pure!

2. Christmas with the Kranks has some of my favorite one-liners and everyone’s obsession with Frosty sleighs me.

Erin Hamilton

New Business Director


1. Home Alone 2 – Lots of love to the original but I prefer the NYC version and especially Kevin’s excessive (or reasonable?) use of room service.

2. The Holiday – Come for the love stories, stay for the perfect yet inaccessible real estate. I especially love Jude Law’s daughters with their adorable accents.

3. It’s A Wonderful Life – An absolute classic I can’t watch without crying. 

Kate Arends

Creative Director, Founder


1. White Christmas – This movie is a classic, and I watch it every single year. It brings back a sense of nostalgia I can’t quite describe.

2. Die Hard – I’m on the same page as Bridgette with this one. There’s something about the overall plot (and, I mean, Bruce Willis) that gets me every time.

3. The Family Stone – I don’t know about you, but I find this movie refreshing for its portrayal of a family that isn’t perfect, one with both plenty of love and also plenty of things to work on. It’s a holiday movie that’s more honest (and just as entertaining, in my opinion) than so many others.

Raquel Benedict

Graphic Designer, Illustrator, and Art Director


1. This isn’t a movie but it’s the first thing I thought of: I cannot go a holiday season without seeing The Nutcracker. The theaters! The costumes!! The LIVE SYMPHONY ORCHESTRA!!! I add the final song of that symphony to every single playlist of mine during this time of year and will fight anyone who says its not one of the most beautiful things they’ve ever heard. I just learned that there is actually a movie rendition of The Nutcracker but I am not ready to vouch for it until I watch!

2. As for movies…Love Actually really tugs as my heart. I can’t resist the movies where all these different people are living in the same storyline but don’t even know it! Also: Accents. Also also: Professor Snape.

3. Another favorite is The Polar Express. It’s such a sweet story with magnificent music. I remember watching it when I was 8 or 9 and then getting to go see the Holidazzle Train come through my hometown. Magical. I’m ready for a live-action!!

Jackie Saffert

Editorial Director


1. The O.C. Chrismukkah episode (Season 1) – I know, I know. It’s not technically a movie. But, as all of my friends know at this point (I talk about it every year—I can’t help myself), this is my go-to holiday entertainment. For me, an early 2000s teen, it brings nostalgia in its finest form.

2. The Holiday – I know there’s an air of cheesy romanticism in this movie, but folks! That hasn’t stopped me before!! I love the stories in this movie, and I think there’s a part of me that likes to imagine skipping off to England at a moment’s notice (can you blame me?).

3. Home Alone – This was one of my favorite movies to watch as a kid, and it continues to be to this day. While the plot itself is rampant chaos at times, the characters and scenes that I’ve been watching for almost three decades (!!!) feel like home.

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