My Definitive Guide to Holiday Movies*

*entirely subjective, favors Muppets

We are barreling headlong into a holiday season that is under a government mandate to be both Holly and Jolly; the unrelenting chaos of this epoch means that ol’ Kris Kringle is working triple-time to ensure that we’ve still got enough good will towards men to get through just one more week of this completely unhinged year!

Despite ending the year with a gigantic to-do list, I have fully cleared my calendar for revelry. I’ve been listening to Vince Guaraldi since September, I purchased eggnog in November, and I was so ready to deck these halls that I misjudged my tree-to-ceiling ratio and had to hack off the top 6” with a bread knife.

But my favorite harbinger of yuletide cheer is The Christmas Movie. I am an expert in The Christmas Movie; it is one of my favorite genres that, when done well, becomes part of your own family lore.

Behold, an almost-exhaustive list of my Very Favorite Christmas Movies, and where you can watch them over this deliriously cheese-filled week.

Honorable, but obvious mention:
White Christmas, Home Alone, Home Alone 2: Lost in New York, The Santa Clause, Die Hard, Die Hard 2, The Grinch (original/Jim Carrey), Miracle on 34th Street (original)

The Muppet Christmas Carol

My desert island Christmas movie

This 1992 adaptation starts playing on Disney+ before Thanksgiving and it doesn’t stop until January is nearly over. There is nothing childish or insincere about this movie. This was the first project that the Henson company took on after Jim’s sudden death, as well as the death of beloved Muppet performer, Richard Hunt (Scooter, Sweetums, Janice) to the AIDS epidemic. There’s a somberness that pervades the whole movie as the group discovers how to keep the soul of the Muppets alive without Jim. And yet—that struggle is what makes it so tenderly magical. The puppeteers pour their aching spirits into this evergreen story about not taking life and love for granted, our hearts swelling and breaking to Paul Williams’ music, our hands amicably and familiarly held by Gonzo and Rizzo as we adjust to a new Kermit, and to a world without Jim.

And then—oh, then—there is Michael Caine.

One of my favorite bits of wisdom I’ve seen is that whereas the Muppets treated Tim Curry like a fellow Muppet, Michael Caine treated the Muppets like people. His journey from hardened cruelty to Santa himself does Dickens proud, but it’s the vulnerable pockets of fear and doubt you’ll spy in the moments of Christmas cheer that elevate and humanize his performance to legendary status. Disney+

A Muppet Family Christmas

Childhood fever-dream (wholesome)

It’s 1987, and Jim Henson has cooked up quite a festive meal for us—starring the Muppets, the Sesame Street gang, and the Fraggles—all under one roof! There’s a snowstorm, Fozzie forms a comedy duo, and in my favorite C plot of all time, Swedish Chef is intent on cooking the goobla goobla humongo when he sees Big Bird walk through the door. This is a dizzying rush of 40 minutes that I can’t stop rewatching, and since licensing issues keep it off the streamers, you can find it complete with original ‘80s commercials on YouTube.

Babes in Toyland (1986)

Childhood fever-dream (disturbing)

If you prefer your nostalgia tinged with unease, might I suggest a movie I was sure was a dream, brought on by an undigested bit of beef? It’s 1986’s Babes in Toyland, starring an on-the-brink Drew Barrymore, a pre-Bill and Ted Keanu Reeves, national treasure Pat Morita, and Empty Nest’s Richard Mulligan and his Nosferatu cronies as the enemies of Christmas/equal rights. It’s eerie to watch 11-year-old Drew in the dark labyrinth of addiction, and it’s not helped by an avalanche of nightmare fuel: Muppet rejects, compost zombies, and a 50-something year old man trying to forcefully marry a teenager. But not to worry—the whole thing is lifted by a raucous devotional to Cincinnati, Ohio that is well worth the 145 minute runtime! Prime

Ernest Saves Christmas

A nostalgic slapstick ride

The more time goes by, the more I appreciate Jim Varney as an American treasure and a brilliant comedian. I can’t stop watching this goofy ‘80s timepiece that shows off Varney’s sketch comedy prowess, a Santa plot that recalls Miracle on 34th Street and pre-dates The Santa Clause, and truly what must be the worst part of the year for poor Vern. KnoWhutImean? Disney+

Scrooged

Bill Murray’s best

It would be impossible to choose between each perfect moment—from the screen career that Buster Poindexter was born for, to Alfre Woodard’s put-upon Bob Cratchit, to the satirically Emmy-winning live network production of A Christmas Carol starring Buddy Hackett, and you’re going to make me pick??

The best part of this movie isn’t in the script. Murray’s titular come-to-Jesus moment is broadcast on live TV, and after a pretty breezy performance throughout, he makes a hard left turn, switching tones entirely. The man comes through with such earnest fervor, such heartrending catharsis, that I end up in tears every time along with him. Because Murray isn’t on script anymore—Murray is begging himself, begging us all, to remember the sole imperative of this world: that we show up for each other. The miracle can happen, it can happen for you. Prime

The Family Man

The heartstring-plucker

Once in a blue moon, Nicolas Cage will really surprise me, and this is a perfect example of that. In a sort of reverse It’s a Wonderful Life, a deeply wealthy and deeply isolated CEO is spirited back to the tire salesman life he could have led with his first love if he hadn’t taken a banking internship overseas. Somehow, Cage is both perfect as the steely CEO and as this man softening, unwinding, an alien in this family, diligently learning how to be tender and relational. You cringe when he stumbles over his old values. Tea Leoni is grounded, playful, and sensual as the love he left at the airport, and you will cry when he finally gets it right. Netflix

Last Holiday

100% hygge

There is SO much to love about Last Holiday. Queen Latifah stars as the wallflower would-be chef Georgia, who can’t stop denying herself. She cooks delicious meals and refuses to eat them, she stays in a terrible job and can’t bring herself to ask out her loverboy freak co-worker LL Cool J, and she’s never spent a penny on herself. When she finds out she has a rare terminal condition, she liquidates her assets and flies first class to the Grandhotel Pupp in Prague, where you will spend the next 2 hours watching her get a makeover, get massages, eat every gourmet meal, and become inseparable best friends with Gerard Depardieu, all against a freezing backdrop of alpine wonder. This is pure coziness that just gets better as LL Cool J goes full Taken to find her. Prime

Batman Returns

The only superhero film I need

Marvel can’t come anywhere close to this classic: incredible practical effects, Michael Keaton, superb stylistic direction by Tim Burton, Danny DeVito in the only acceptable fat suit of all time, Christopher Walken at near-peak villain, a Paul Reubens cameo, the creepiest Catwoman origin timeline, and constant reminders that this is, in fact, a Christmas movie. (If you crave Burton but not Batman, remember that Edward Scissorhands is also a Christmas movie.) Max

Hook

The blockbuster fantasy

An all-time favorite for me, it’s just handy that Spielberg folded Christmas into this return to Neverland. Not a beat is missed—and somehow, the only performance better than our beloved Robin Williams as Pan the Man is Dustin Hoffman as an IMPOSSIBLY excellent, funny, nefarious and dark Captain Hook. The sets are otherworldly, we get Bob Hoskins and Dame Maggie Smith AND an incognito Glenn Close, and every kid wanted to be head lost boy Ru-fi-o! Ru-fi-o! Ru! Fi! Ohhhhhhhhh! Peacock

The Holiday

The best holiday romance of all time???

Firmly, yes. There’s simply no contest. Nancy Meyers has obliterated the genre for anyone else. Jude Law is at his most timeless and lovable, Cameron Diaz is pure sassy joy, Jack Black has criminally NEVER AGAIN been utilized so perfectly for his playful, flirtatious, earnest and tender heart, which is shocking given his performance here. But the beating heart and soul of this movie, hands-down, is Kate Winslet. After years of pining for a man who cannot and will not love her, Iris finds her gumption again when she goes on holiday to LA and meets Hollywood legend Eli Wallach, who introduces her to the self-possessed Hollywood starlets of classic movies. As she brushes up on her Hepburn and Bergman and Garbo, we thrill for her growing boundaries and sense of self—and for the right guy to finally sing her song. Prime

While You Were Sleeping

Best holiday rom-com of all time

If you’ve never seen this Perfect Movie, it is my extreme pleasure to introduce you to the best 90 minutes ever committed to celluloid. While You Were Sleeping is set in Chicago, not New York, and it’s a cheese week movie—meaning, it’s not about Christmas. It’s about all the nebulous, liminal, endless-leftovers time between Christmas and New Year’s. It is about our lonely hero and public transit worker Sandra Bullock, and how when the day-trader she dreams about is jumped on the tracks of the L train, she finds herself tangled in a snowballing lie when she’s introduced to his (very loud, very Irish, very Catholic) family as his fiancee. Sandy is heart-on-her-sleeve unpolished, there’s a no-notes Peter Boyle as the Callahan patriarch, Peter Gallagher is *hysterical* when he finally comes to, and Bill Pullman is the definition of the word “rakish” with blue-collar charm to spare.

And still, they are not the best part of this movie.

Michael Rispoli, as Joseph Fusco Jr., will change your life.

These chains! This midriff! This mouth acting!! And just when you think he’s all caricature, he hits you with a gutpunch of vulnerability that tenderizes him like a nice slice of prozhoot. And you’re telling me he never won an Oscar for this??? Disney+

That’s it, my top 10 of mostly-innocuous holiday movies. I wish you lots of cheese and lots of happy viewing! Happy Holidays, friends.

xx Jen