Our Favorite Christmas Movies in View Order (2021 Edition)
“For a couple of hours out of the whole year, we are the people that we always hoped we would be!”
— Frank Cross in “Scrooged”
Every fall beginning at Thanksgiving, or right after, I start to feel the inward and reflective pull of winter—and this pulls me into and through winter’s coming and into the Christmas season. These are the films we love to see this time of year to remind us what this season is all about.
The films are organized by timeline—the organic order we watch these every year to get ready for the season. You can watch them in any order you want but I’m required to mention that some of the links below are affiliate links to Amazon meaning that someday I could get paid for sending business their way.
Pre-Thanksgiving: Because These Are Thanksgiving Films
The story actually takes place at Thanksgiving so adjust your calendar appropriately. It’s a comedic family drama with some brilliant moments of the younger generation standing up to become themselves and owning who they are.
Directed by Jodi Foster. Stars: Holly Hunter, Robert Downy Jr., Anne Bancroft, and Claire Danes.
Here’s another everyone-coming-home-(out?)-for-Thanksgiving story. Yes, another comedic family drama about Thanksgiving. It’s a very indie film with all the wonder of small indie films including some flat sections and less convincing acting in places, but overall a great story that the telling of it doesn’t get in the way of overall spirit. One of the first films to really show us the family dynamics of whether it’s safe to be gay and come out to your family during the holidays.
Written and Directed by Jenna Laurenzo. Stars Jenna Laurenzo, Caitlin Mehner, and Deirdre O'Connell.
Thanksgiving Through Early December
Nightmare Before Christmas (1993)
Tim Burton and Danny Elfman create a lens through which Jack Skellington, the Pumpkin King of Halloween Land, investigates the mysteries of Christmas. Jack Skellington is one of the most charming skeletons ever caught on film. And Jack is voiced by Prince Humperdink!
Is this a Halloween or Christmas film? Well, we watch it every Thanksgiving and a great entrance into the holiday season—whichever holiday.
Ok, I know, not contemporary and not a Christmas movie. The story takes place at a Christmas party and I had to mention it as one of our favorites to watch this time of year.
Stars: Bruce Willis, Alan Rickman, Bonnie Bedelia, Reginald VelJohns, Alexandar Godunov (yep, the Russian ballet dancer)
Early to Mid-December
Time to start thinking about Christmas coming.
This is Christmas Vacation without the family and with one clever kid who finds some new meaning at Christmas.
Stars: Macaulay Culkin, Joe Pesci, Daniel Stern, Catherine O’Hara.
This is a great first step into the joy of comedic family dramas about getting together at the holidays. It’s breezy enough to not really feel like a Christmas film. This one comes close to being a “holiday shenanigans” movie.
Stars: Vince Vaughn and Reese Witherspoon.
Not as good as the original film, “Bad Moms,” IMHO, but a Christmas buddy movie that does get at family dynamics during the holidays, particularly mother-daughter relationships.
Stars: Mila Kunis, Kristin Bell, Kathryn Hahn, Christine Baranski, Susan Sarandon, and Cheryl Hines.
Ridiculous Holiday Movies That I Can’t Recommend ;)
If you’ve ever worked for a large organization where people work together and then are put in a situation to have to be social... What would you do to save the company you work for? Throw a Christmas party?
Stars: TJ Miller, Jason Bateman, Olivia Munn, Jennifer Anniston, and a ton of others.
A slant retelling of the Scrooge story as a buddy film and romantic comedy where three friends finally get invitations to “the big holiday party” during their last Christmas together. I know, the conceit sounds odd, but this one has heart.
Stars: Seth Rogen, Joseph Gordon-Levitt, Anthony Mackie, Lizzie Caplan, Jillian Bell, Mindy Kaling, and Michael Shannon.
A Very Harold and Kumar Christmas (2011)
Two friends are reunited at Christmas by a magic joint from a very special person. Lot’s of hijinks, Neil Patrick Harris, the mob, and a waffle bot.
Stars: Kal Penn, John Cho, Paula Garces, Danny Trejo, and Neil Patrick Harris.
National Lampoon's Christmas Vacation
Christmas with the Griswolds may seem a little too familiar depending on your family. Easily the favorite Christmas comedy.
Stars: Chevy Chase, Beverly D’Angelo, Johnny Galecki, Juliette Lewis, Randy Quaid.
When You’re Ready to Settle into the Holidays
This is a strange balance of family comedy-drama, coming home for the holidays, mixing with old friends and new, and possibly coming out to your family. I really dig how they pulled this one off. Only on Hulu and the free trial is worth it.
Stars: Kristin Stewart, Mackenzie Davis, Dan Levy, and Mary Steenburgen.
We love this film and actually watch it a couple of times a year. Kate Winslet and Jack Black are especially charming as they find themselves following break ups. Eli Wallach is so good too. Super charming film.
Stars: Kate Winslet, Jack Black, Jude Law, Cameron Diaz, Eli Wallach, Rufus Sewell.
The story takes place at Christmas but we don’t necessarily see the powerful character transformation like we do in what I consider to actually be Christmas movies. I know, that was too much. However, I think writer/director Richard Curtis really tries, and mostly succeeds, showing the many different aspects of love.
Stars: Hugh Grant, Keria Nightly, Liam Neeson, Emma Thompson, Colin Firth, Bill Nighy, Alan Rickman, and a lot of other fantastic actors.
A favorite of many people for good reason. What is our impact and how do our choices effect our impact?
Stars: Jimmy Stewart, Frank Capra, Donna Reed, Lionel Barrymore, Karolyn Grimes.
I really enjoy watching this film every year. It’s pretty simple, but the play within a play idea works well. And the music is fantastic.
Stars: Vera Ellen, Rosemary Clooney, Danny Kaye, Bing Crosby, Dean Jagger.
How the Grinch Stole Christmas (1966)
Not really a movie, but a tv special. Anyway…
I think this is my favorite Christmas story. Bill Murray’s acting is fantastic. There’s humor, heart, and hope here. Highly recommended.
Stars: Bill Murray, Karen Allen, Carol Kane, Bobcat Goldthwait, Alfre Wood, Robert Mitchum.