8 Movies I (Re)Watch Every December

It’s that time of year again, and yet every single Christmas season never fails to inspire, excite, and touch my heart. Each December as we drag out the decorations and stock up the freezer with fudge and gingerbread, we also pull our favorite holiday movies out of the cupboard.

So this month, I’m wandering off the Trail of Rose Michaud. Just for fun, I’ll share the movies on our family’s annual list:

1. Casablanca

Let’s start with this one, a 1942 romantic drama which won multiple Academy Awards. It’s hard to beat Humphrey Bogart and Ingrid Bergman. Some call it the best Hollywood film of all time, made in the middle of the Second World War.

But you’re maybe wondering why watch it at Christmas? Although it’s set during a wartime December (in Nazi-controlled French Morocco), it’s far from a Christmas story. Doesn’t even mention it. Rather, Casablanca portrays a dark period in a “weary world.” Everything—the outcome of the war, the value of sacrifice, even of life—remains up in the air, in the film and in real life.

“Christmas is a necessity. There has to be at least one day of the year to remind us that we’re here for something else besides ourselves.” —Eric Severeid, WWII news correspondent

Yet amid all that looks so bad, “a thrill of hope” resounds. There isn’t much of that these days, is there? Alongside the wonderful (and tragic) love story, themes of redemption and transformation prevail. Besides, Casablanca has some memorable lines!

2. Miracle on 34^th Street

This one usually shows first in our annual lineup of holiday movies, because the opening scene takes place on Thanksgiving Day. Maureen O’Hara, a wonderful actress from classic Hollywood days, fires a drunk Santa and hires nursing home resident Kris Kringle to replace him for the Macy’s Parade in New York City. (Did anybody else watch those parades on TV every Thanksgiving morning as a kid?)

“Oh, Christmas isn’t just a day. It’s a frame of mind.” —Kris Kringle, Miracle on 34th Street

Due to life’s disillusionments, neither O’Hara’s character nor her little daughter believe in Santa Claus, though. A lawyer friend sets about to prove Santa’s existence in court. (And remember, if you don’t believe in Santa Claus, you get underwear!)

“Faith is believing in things when common sense tells you not to.” –character Fred Gailey, Miracle on 34th Street

3. Holiday Inn

Holiday Inn represents the collection of vintage Christmas movies we’ve received as gifts over the years. It was probably the first, sent to Chile from a cousin back in the ’90s.

This is the Bing Crosby-Fred Astaire special which first featured the classic holiday song, “White Christmas.” Here, an entertainer “retires” to a Connecticut farm which he converts to a dinner-and-show inn that runs only on holidays. A year-long competition ensues between the men for the love of a bright new female star.

It’s a light-hearted blast of laughs—fun and funny.

“It is Christmas in the heart that puts Christmas in the air.” –W.T. Ellis

4. White Christmas

Here’s another of our movies with a World War II connection and also another Bing Crosby musical tour de force. Oh, the music! Oh, the dancing! The costumes and comedy!

In White Christmas, Crosby teams up with a troupe of his “show biz” friends to honor a beloved former commanding officer while saving the man’s Vermont ski hotel from failure. And wouldn’t you know? Of course, the snow arrives right on time, on Christmas Eve.

“If you’re worried and you can’t sleep, count your blessings instead of sheep. Then you’ll fall asleep counting your blessings.” —character Bob Wallace, White Christmas

5. An Affair to Remember

This 1957 classic starring Cary Grant and Deborah Kerr has a famous link to another “to-me” Christmas movie, Sleepless in Seattle, which shares some of the same plot tropes. An Affair to Remember frequently surfaces from oblivion on Valentine’s Day. But since it climaxes on Christmas Eve, I like to include it among my favorite Christmas movies.

In the story, a pair of lovers spends some time apart after a whirlwind romance while they try to figure out whether the other is “the one” for them. Kerr’s character has a paralyzing accident on her way to meet Grant at the Empire State Building. However, she refuses to let him know, not wanting to chain him to her.

“Some Christmas tree ornaments do more than glitter and glow, they represent a gift of love given a long time ago.” —Tom Baker, from Doctor Who

But in his love, he pursues her. If you haven’t seen this movie, I won’t include spoilers here. Instead, check out for yourself how the guy discovers the truth about his girl’s aloofness. I just love the element of sacrifice involved in true love shown in this story.

6. While You Were Sleeping

Sandra Bullock and Bill Pullman star in this more modern romantic comedy about a Chicago train attendant who saves the life of her crush and is mistaken for his fiancée by the hospital staff and then the family.

Bullock’s character’s a lonely girl who has recently lost her beloved dad to cancer. While her “fiancé” lies in a coma over the Christmas season, she falls in love with the guy’s brother. But she also falls in love with the whole family and wins their affection and welcome when she eventually gathers the courage to confess the truth.

While You Were Sleeping highlights the gift of family love. If you have one, thank God for the blessing and celebrate every minute you have with them.

7. The Family Man

In this romantic fantasy, Nicolas Cage and Téa Leoni play a young couple who threw away love, marriage, and family for their careers. Years later, on Christmas Eve, Cage’s high-roller character is gifted a magical chance to experience the life he might have lived had he made different choices.

“One of the most glorious messes in the world is the mess created in the living room on Christmas Day. Don’t clean it up too quickly.” —Andy Rooney, from 60 Minutes

While I’m not really a Nicolas Cage fan, this tale points out so clearly that some things have far greater value than power and possessions. And that you should never, ever let go of love lightly.

Critics have likened The Family Man to other classic Christmas movies, but with a twist rather than a typical happy ending. It explores “the path not taken”—what I call the big “what-if’s” of our lives. In fact, it’s kind of a mirror version of…

8. It’s a Wonderful Life

Isn’t this one of the best movies of all time? Since I discussed it in a post from last year, I won’t dive deep into the details today. I’ll just say that I keep It’s a Wonderful Life especially for Christmas Eve, probably because it climaxes then and there.

Briefly, James Stewart plays a faithful guy who has big dreams of escaping his small hometown…and never does. A financial disaster leads him to thoughts of suicide, which lead to a reexamination of his life’s accomplishments. And they definitely amount to so much more than he ever imagined.  

“Strange, isn’t it? Each man’s life touches so many other lives. When he isn’t around, he leaves an awful hole, doesn’t he?” —angel character Clarence, It’s a Wonderful Life

The film doesn’t top my list for its theology of angels 😊. But its philosophy on life’s inevitable disappointments offers pure gold for any and all of us who may have lost faith and perspective.

So…look up your Christmas movies this month. Sometimes our family views them together, sometimes apart. Sometimes I enjoy them in the background while I bake. Or while reading, writing, or crafting.

Any suggestions to add to my list?

Maybe like me, you also delight in the animated childhood classics like How the Grinch Stole Christmas, A Charlie Brown Christmas, and Rudolph the Red-Nosed Reindeer. Or comedies like Home Alone. I picked Operation Christmas Drop out of the sentimental sea of Netflix movies last holiday season, and it was pretty good.

Not a Hallmark fan? How about seeking out your favorite Christmas passages in books? The puffed sleeves of Anne of Green Gables, the tin cups in Little House on the Prairie, the arrival of Father Christmas and the break-up of “always-winter-but-never-Christmas” in The Lion, the Witch, and the Wardrobe. Little Women begins on a beautiful Christmas morning too.

One of my books, The Seahorse Patrol, features extensive Christmas scenes as it builds to the climax and resolution through the month of December. It’s the first book in the First Mate’s Log series, the next up after I finish Legacy of the Linnenbrink Light. (Be on the lookout this year.) The Seahorse Patrol has all the holiday goodies: a wedding, a surprise family visit, a cookie-baking marathon, and a grand party with special gifts.

Whatever your taste—in movies or books—may you find something about all these stories that fills your heart with the transforming joy and hope of the season of Jesus’s birth.