The holiday season is a time when friends and families get together, the days get shorter, and the weather gets colder.

We tend to eat too much, drink too much, and let everything that happened throughout the year fade away.

So, what’s a better way to put the rest of our lives on pause than to cozy up with a bag of fresh popcorn… a glass of red wine… and flip on a classic movie?

Sure, there can be some controversy over who has the best list.

And yes, the art of coming up with comprehensive movie lists this time of year entails much debate…

Over things like is Die Hard truly a Christmas movie? (It is!) And how many times can any one person watch Love Actually? (Dozens.)

But at Inside Wall Street, we’ve got you covered with something different. You’re here, which means you have financial or economic interests as well.

Yesterday, I gave you my top five books to read – or gift – this holiday season.

And today, I’m bringing you a list of some of my favorite movies to watch during the holidays.

It meshes movies and money, but with holiday cheer in mind.

1) The Muppet Christmas Carol (1992)

If you’ve not seen this Disney Christmas classic, it offers such a terrific balance of fun, humor, and a bit of Christmas glee (with a side of humbug).

Yes, Mr. Scrooge is a brutal businessman. But this movie’s economic and very human message, derived from the Charles Dickens story, has something for everyone.

2) Planes, Trains and Automobiles (1987)

John Candy and Steve Martin are perhaps at their all-time best in this film about an odd friendship of sorts.

Yes, this is more about Thanksgiving than Christmas. But still, the movie pokes fun at holiday chaos, social divisions, and the demands and challenges we all face – in an enjoyable and silly way that nearly everyone in your family can enjoy.

3) A Christmas Story (1983)

Every year, the story of Ralphie plays on a marathon loop. Yet every year, so many people get drawn in by this enthralling tale and then can’t turn it off.

Maybe the economic message here is general in scope. But the fact of the matter is that this family growing up in Cleveland, Ohio, is one that many families can still relate to.

Its patriarch is a hard-nosed, hard-working father who’s ruthless for a deal… yet learns that what matters most is his family, the spirit of the holidays, and the simple things in life.

4) It’s a Wonderful Life (1946)

This Frank Capra classic has it all. I watch this movie every year. And every time I do, I always get something else from it that moves me.

The film traverses the Depression-era times of George Bailey and his family, while intertwining with the Dickens classic, A Christmas Carol.

The message of working hard, caring about your neighbors, and doing the right thing is one that goes perfectly with a warm cup of hot cocoa.

5) National Lampoon’s Christmas Vacation (1989)

Clark Griswold is the dad, husband, and uncle that wants to deliver the perfect Christmas. Yet despite it all, the world keeps getting in his way.

This film’s economic and practical life themes come to a head when his boss unexpectedly slashes the holiday bonus without any warning – and hilarity ensues.

6) A Charlie Brown Christmas (1965)

The ultimate feel-good movie.

Charles M. Schulz and his Peanuts classic really do remind us what the holiday season is all about.

Being together with the people you care for the most is what matters the most.

Yes, we can often get caught up in gifts, decorations, and the seasonal buzz. But the message here is clear for old and young alike.

Bonus Pick – Catch Me If You Can (2002)

Okay, this is not truly a holiday movie. Yet, there are Christmas and holiday scenes that set the tone.

If you’ve not seen this, it’s a biographical crime comedy-drama by Steven Spielberg.

It’s based on the story of Frank William Abagnale Jr. – a conman and an infamous fraudster who traverses the world.

It’s as shocking as it is compelling. And so much fun to watch.

And there you have it. Movies you can watch with the family this holiday season – with just the right mix of holiday cheer and financial wisdom.

Do you have any other go-to holiday movies on your list? I’d love to hear them! As always, write me at [email protected].

Happy Holidays!



Nomi Prins
Editor, Inside Wall Street with Nomi Prins