City Cast Portland logo

The Best Holiday Movies

Posted on December 13, 2023   |   Updated on September 30, 2025
Adrian González

Adrian González

people lying on a floor with white Christmas lights watching a screen

Warm up your hot cocoa, we’re getting festive. (evgenyatamanenko / Getty Images)

‘Tis the season for cozying up on the couch and binge-watching holiday movies. The only problem is that there are so many to choose from that picking what to watch can be a chore. Here’s a good place to start.

The Classics

Let’s start off with the easy choices — I’m talking “Home Alone,” “Elf,” or “Love Actually.” These are best for when you don’t want to endlessly scroll for options, or when you just want a crowd-pleaser. Here are a few other favorites.

  • “The Holiday” — Who knew Jack Black could be charming?
  • “Little Women” — You have three film adaptations from which to choose!
  • “The Nightmare Before Christmas” — We’re all a little bit of Jack Skellington.
  • “A Christmas Carol” — This one also has three different film adaptations.
  • “Scrooged” — Or you could watch Bill Murray in the modern adaptation of the Charles Dickens novel.
  • “Carol” — One of the most beautiful on-screen affairs.

A Word About ‘Bad’ Holiday Movies

As an equal-opportunity movie lover, I encourage you to watch whatever flicks you enjoy without an ounce of shame. There is simply no denying the hot-soup levels of comfort you can get from watching Hallmark movies and holiday rom-coms. Don’t let film bros tell you otherwise. One that I enjoy to an unreasonable degree is “Felíz NaviDAD,” starring Mario Lopez and his adorable dimples.

Bruce Willis crawling on his belly

Is “Die Hard” a Christmas movie? (Courtesy of Twentieth Century Fox)

Something Different

  • “Die Hard” — The debate on whether this is a Christmas movie rages on. Regardless, it’s a great time to watch.
  • “Black Christmas” — A 1974 gory horror classic.
  • “A Serious Man” — Comedy cringe a-la Coen brothers.
  • “The Lodge” — For the horror fans who want to partake in the holiday spirit.
  • “Santa Claus” — No, not the one with Tim Allen. I’m referring to the 1959 Mexican film, chock-full of weirdness.
  • “The Ice Harvest” — John Cusack as a conniving lawyer pulling a Christmas Eve con is quite enjoyable.
  • “Tangerine” — One of my favorites from 2015, this one follows a transgender sex worker in L.A. And it was all shot on an iPhone.

Happy watching!

What Are Your Favorite Holiday Movies?
see more:art

Share article

Hey Portland

Stay connected to City Cast Portland and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.
Advertisement image

Portland's Best

See All
Portland's BestJuly 30

What To Do in Portland in August 2026

We have some ideas for how to make this month in Portland more exciting, easier, and just an all-round good time.

Green fish or shark like head with pointy teeth and a tongue hanging out is this soapbox derby entrant. People and a van and trees in the back.
Portland's BestJuly 1

What To Do in Portland in July 2026

A quarter millennium ago, the U.S. got its start. Since then, we've experienced all the promises and disappointments of our country's rhe...

Parade with people in pink and rainbows.
Portland's BestJune 15

Tips For Getting the Most Out of Summer

The City Cast Portland team shares their favorite Portland summer hacks — tips for cooling down on hot days, favorite patios, the perfect...

People biking through an arch-shaped water mister on a street lined with cars and trees on a clear day.
Portland's BestJune 2

What To Do in Portland in June 2026

City Cast Portland contributor Alex Frane has a couple picks:

cyclists out for a group ride on a leafy street in Portland, Oregon
Portland's BestApril 30

Your Guide to May 2026 in Portland

From Mother's Day brunches to 503 Day celebrations to the Primary Election, there's going on in Portland this month.

People on a podium having shot off confetti.
Portland's BestApril 1

Your Guide to April 2026 in Portland

Out on the Oregon Coast, April means it’s time to celebrate the puffin’s seasonal return to Cannon Beach, which will host an annual Puffi...

A closeup of a tufted puffin.
Portland's BestMarch 16

Where to Find Downtown Portland's Best Hotel Bars

With the opening of Damian Lillard's shiny new bar at the Benson Hotel, I've been thinking a lot about our city's hotel bar scene. For me...

people sitting curved banquettes and tables, at Abigail Hall, Portland, Oregon
Portland's BestMarch 9

Where To Indulge in the Cherry Blossom Bloom This Year in Portland

The yearly cherry blossom bloom along the waterfront is one of the rare times you'll see a crowd in our city outside of a scheduled event...

cherry blossoms at the Tom McCall Waterfront Park, Portland, Oregon, park bench foreground

The latest in Portland

The Weekly Wander by City Cast PortlandAugust 16

Your Guide to Portland's Hawthorne District

There’s always something going on in the Hawthorne District, it has lots of places to get lost (in a good way), and everything is incredi...

Two people walk along the crosswalk outside the Bagdad Theater & Pub, a historic building along Portland’s Southeast Hawthorne Boulevard. Its Middle Eastern-inspired marquee shows times for “A Quiet Place, Part 2”.
The Weekly Wander by City Cast PortlandAugust 16

Side Quest: The Great Indoors in Portland

If you happen to be on Hawthorne Boulevard when the sky’s hot and hazy, here are some ways to still have fun inside.

An ochre couch sits in the showroom at Vintage Pink in Portland, Oregon.
Portland, ExplainedAugust 12

How Well Do You Know the Oregon Coast?

If you’re looking for an escape from the next heat wave, there’s no better place to be than the Oregon Coast.

Lighthouse on a rocky promontory surrounded by blue.
The Weekly Wander by City Cast PortlandAugust 9

Your Guide to the North Shore

It’s not as shiny as Vancouver’s waterfront, but there’s plenty to do and see if you know where to look, so let’s dive in.

Alternating images show scenes from the 2025 edition of the Portland Classic, a non-major tournament on the LPGA Tour.
The Weekly Wander by City Cast PortlandAugust 9

Side Quest: Keep Calm and Paddle On

Whether you’re paddling a kayak, a canoe, or a stand-up paddle board, spending time exploring Portland’s waterways is a huge perk about w...

A person floats on greenish-blue water in a yellow kayak, photographed from above.
Summer GuideJuly 30

Tips for a Better August 2026 in Portland

August is our hottest month, so we all need to figure out how to stay cool in Portland - check out a few tips we've gathered.

The Oregon coast with haystack rocks off the shore and a wide beach.
Summer GuideJuly 27

The Most Overrated (and Underrated) Portland Summer Activities

Summer in Portland often feels ideal — the weather is mostly moderate, and there's an endless list of events and outdoor destinations to...

A mossy and rocky terrain with a steep cliff covered in trees in the background.
The Weekly Wander by City Cast PortlandJuly 26

Side Quest: Stop and Smell the Roses

Although you’ll now encounter a multi-hued oasis, when the garden opened in 1913, it was planted with nothing but fragrant, pink roses.

Two people walk their bicycles through an ornamental rose garden, popping with vibrant red, pink, and white blooms.