My Holiday Movie Line-Up

The 5 films I try to watch every year

1. It Happened on 5th Avenue (1947)

I’m sure my old movie-loving father introduced me to this, as it’s not high on the rotation for most. But it’s so charming, and a classic vintage New York comedy. There’s also a very cute dog. My synopsis is below, but it’s also fun to go in blind and enjoy each little twist.

An elderly serial squatter makes his annual visit to the 5th Avenue mansion of a real estate tycoon, who usually is out of town for the season. When his heiress daughter runs away from finishing school and heads back to the city, she is surprised to find not only him, but a group of drifters in her house, including a young war veteran she quickly has eyes for.

Instead of revealing her rich girl identity, she pretends to need a place to stay and woos him. When her father returns home to find her, she convinces him to begrudgingly play pretend with the visitors.

This is such a good hidden gem!

More vintage chaos…

2. Christmas in Connecticut (1945)

Chaos, a career reckoning, and the resulting comedy go hand-in-hand with Christmas in this silly romance. It has everything: a quirky character actor, a wandering cow, a baby swallowing a watch, and a woman who must prove herself Ina Garten-esque to her editor and her unexpected guest.

In it, a popular magazine columnist is asked to make a POW survivor’s Christmas wish come true, and quickly must make the imaginary homemaker life she writes about a reality—or at least put on a good show of it. She immediately falls for the soldier, which greatly complicates the escapade, wherein she’s pretending to be married, a mother, and fabulous cook.

It’s worth a watch for the outfits alone. I always wear a gown and fur bolero on Christmas!

Now for something in color…

3. Meet Me In St. Louis (1944)

This has always been one of my mother’s favorites, and we first watched it when she got the VHS for Christmas one year when I was a kid. Technically a four-season vs. purely Christmas film, this eye candy musical captures a midwest family in flux as they celebrate the World’s Fair coming to their city, while they simultaneously recieve the news that they’re moving.

Judy Garland positively glows in this movie, which was directed by her future husband.

The youngest sister is played by Margaret O’Hara, a standout and perfect match to Garland’s iconic presence. Even if you don’t watch the whole thing, at least watch this…

How about something from this millennium? Okay…

4. The Holdovers (2023)

A new classic, I saw this endearing film in the theater and it’s been in the rotation ever since. When we walked outside after, I really expected to see snow on the ground, that’s how transportive it feels. If you really watch it (no phones!) you’ll see what I mean. The music, the establishing landscape shots, and the classic Northeast scenery is a great stage for the phenomenal acting.

A boarding school teacher is left to babysit the students who have nowhere to go for the holidays. A late-arriving parent whisks most of them away for a ski vacation, but without a permission slip there’s one very complicated young man left alone with the teacher and a grieving school cook, who recently lost her son in Vietnam.

I love any story that gives context, grace, and a chance for transformation to a lifelong curmudgeon (relatable), so this is just delightful to me.

I’m sorry in advance for the last one...

5. The Family Stone (2005)

I know, I know. This is hardly a sleeper find. But it’s so touching, funny, and relatable, not to mention the ambiance… My parents lived in Riverside, CT for over a decade, and the house was right down the road, I always ogled it on the way to church…

For a movie so filled with people and loudly-expressed big feelings, I love the quieter scenes of reflection by the matriarch played by the late Diane Keaton.

Spoiler alert: For anyone who has lost an immediate family member, it is a difficult club to be in (especially during the holidays) and I think telling stories of grief, loss and remembrance are important. Because life is full of…

The end!

I know this list is not exhaustive, but it is personal. I hope you watch something that fills you up. Happy holidays, my friends!