City Cast Madison logo

Cozy Up With the Best Holiday Movies

Posted on December 26, 2023   |   Updated on September 30, 2025
Adrian González

Adrian González

a group of three people is sitting around a screen for a movie

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

Christmas may have come and gone but you can still hold on to that holiday cheer for a little while longer. Gather your new socks and blankets, and cozy up on the couch for some holiday movie binge watching.

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 has a slew of film adaptations, including a Muppets version.
  • “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.

die hard screen shot of bruce willis in a building's air shaft

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 that 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!

Share article

Hey Madison

Sign up for your free daily toolkit to get the most of the city you love.

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

Madison's Best

See All
Madison's BestApril 13

How to Celebrate Earth Day 2026 in Madison

Earth Day is personal for Wisconsin, because it was U.S. Sen. Gaylord Nelson who made it a national day to celebrate and promote environm...

A man in a plaid shirt peruses a rack of clothes.
Madison's BestApril 6

After ‘John Wick,’ Madison-Born Writer Wants Something ‘Normal’

Derek Kolstad may be best known for writing the first three "John Wick" movies. His latest action film, "Normal" starring Bob Odenkirk an...

A sheriff holding a gun is flanked by two other people.
Madison's BestApril 1

Your Guide to April 2026 in Madison

Along with the nicer weather comes the return of the Dane County Farmers’ Market to the Capitol Square on April 11.

A woman arranging purple and white flowers.
Madison's BestMarch 17

Where to Enjoy Classical Music in Madison

From the Madison Symphony Orchestra to the Wisconsin Chamber Orchestra, there are plenty of top-quality classical music groups in Madison...

A conductor in a black jacket waves a baton at musicians.
Madison's BestMarch 11

Where To Celebrate St. Patrick’s Day in Madison

St. Patrick's Day is Tuesday, March 17, and there's lots of ways to get your Irish on in Madison, whether you want to catch an Irish band...

A woman sings while holding a piece of paper.
Madison's BestMarch 10

What To See At the 2026 Wisconsin Film Festival

The 2026 Wisconsin Film Festival takes place April 9 to 16 in Madison. Here's some of the movies that still have advance tickets availabl...

A group of people sitting at tables looking at papers.
Madison's BestMarch 9

Don’t Touch That Dial: Madison’s Coolest Community Radio Stations

If the Spotify algorithm has got you down, Madison's community radio stations want you to tune in. Powered by locals, often volunteers, s...

A white brick building.
Madison's BestMarch 3

How To Celebrate Women’s History Month in Madison

There are lots of ways to honor and highlight the achievements of women in Madison this month, from an all-star tribute show at the Majes...

A woman in a cave reaching out to a bat.