A Classic Hollywood Christmas

Christmas in Connecticut

A listicle? It's never been done before! These are all the classic Hollywood Christmas films I think you'll want to watch while you sew, or drink hot chocolate and pet your dog. I've put them roughly in my order of preference and picked out some key info for each film to help you choose something you'll enjoy. I've also included things you might want to be aware of for each one* so you're not ambushed by blackface or a dog in peril while you're just trying to have a nice festive evening.

*It goes without saying these films are depressingly white for the most part. Just as we've learned using asbestos as fake snow is a bad idea, I hope we can also learn that all white-passing casts are also a bad idea.

The Ultimate Old Hollywood Christmas List

1. Desk Set (1957)

If you only watch one film from this list in December 2024, please make it this one. Although it's absurdly fanciful for the tech of the time, this film is hilariously prophetic on the topic of AI replacing humans and all that comes with it. Plus you get to see Katherine Hepburn being hilarious and brilliant with a backdrop of truly stunning office outfits from 1957. Don't watch the trailer, it gives too much away, just trust me on this one!

Festiv-o-meter: 6/10, Religiosity: Low, Children: None, Animals: Safe and Sound, Costumes: Stunning

2. Christmas in Connecticut (1945)

My longtime favourite Christmas film - Barbara Stanwyck fakes being a tradwife to avoid getting fired, Dreamy sailor turns up, sleigh ride and love ensue.

Festiv-o-meter: 10/10, Religiosity: Low, Children: Low, Animals: Safe and Sound, Costumes: Great

3. The Shop Around the Corner (1940)

It's 'You've Got Mail' before the horror of email was released upon the world. An absolutely lovely holiday romantic comedy with some exquisite character actors thrown in too.

Festiv-o-meter: 9/10, Religiosity: Low, Children: Low, Animals: Safe and Sound, Costumes: Good

4. White Christmas (1954)

This is one I watch every year because the costumes are sensational and it feels so christmassy. I convinced my very modern partner to watch it last year and he said 'That was actually good', so there you go. This was the first film ever shot in VistaVision, which was Paramount's big innovation in film tech in response to 20th century inventing CinemaScope in 1953.

This is a loose remake of the film Holiday Inn, but thankfully they decided to omit the blackface number 'Abraham', and instead we get the minstel-coded but not actually blackface number 'Mandy'. The bar really is on the floor here folks.

Festiv-o-meter: 10/10, Religiosity: Low-Medium in places, Children: Some at the end, Animals: Safe and Sound, Costumes: Stunning

5. The Man Who Came to Dinner (1942)

I guarantee you have seen clips of this before, the script is full of incredible insults. This is a 1942 film adaptation of the 1939 play with the same name and the cast are brilliant. Monty Woolley plays an infuriatingly self important and opinionated radio celeb who slips on the icy steps outside a prominent family's home and threatens them with a lawsuit if they don't let him recover in their house over the Christmas break. He drives them all mad and it's hilarious. Quite a lot of shouting but in a fun way.

Festiv-o-meter: 5/10, Religiosity: Low, Children: Low, Animals: Safe and Sound, and there are a lot of them, Costumes: Good

6. I'll Be Seeing You (1944)

The first drama on the list! I won't say too much about it, but I think it has aged very well and oscillates nicely between complex topics and a touching romance.

Festiv-o-meter: 7/10, Religiosity: Low, Children: Low, Animals: There is one scene where a dog attacks Joseph Cotton but the dog is fine and so is he, they just wrestle for a bit and I'm guessing the scary growls were added in post Costumes: Great

7. Christmas Eve / Sinners Holiday (1947)

This one is three really good stories that all mix into one on Christmas eve. Some fabulous hair and outfits too. I don't want to spoil anything more, just watch it.

Festiv-o-meter: 7/10, Religiosity: Low, Children: Low, Animals: Safe and Sound Costumes: Great

8. Holiday (1938)

A New Years eve film nestled in the Christmas cheer. What it lacks in presents and feasts it makes up for in perfectly capturing the obligations of family parties. This is a delightful film that made my partner laugh from across the room multiple times when he 'wasn't watching it'. I love Katherine Hepburn's outfits in this, Cary Grant is a delight as always, and the Potters are the best!

If you do go looking for this make sure you get the 1938 Katherine Hepburn version and not the 1930s film. They're basically the same story, I just like this one better.

Festiv-o-meter: 5/10, Religiosity: Low, Children: Low, Animals: Safe and Sound, Costumes: Beautiful

9. Remember the Night (1940)

A good guy lawyer and a 'Bad Girl' shoplifter fall in love at Christmas. I love Barbara Stanwyk and she's so great in roles like this. I also desperately want her hat.

Festiv-o-meter: 7/10, Religiosity: Low, Children: Low, Animals: Safe and sound Costumes: Great

10. The Thin Man (1934)

Not strictly a Christmas film but more a film that happens at Christmas while Nick and Nora are visiting New York. Very charming throughout and a fun murder mystery.

Festiv-o-meter: 4/10, Religiosity: Low, Children: Low, Animals: Safe and sound, asta is a star! Costumes: Good

11. The Bishop's Wife (1947)

Imagine if angels were handsome and were trying to steal yo' girl. That is this film. David Niven plays a bishop obsessed with building a new cathedral and Cary Grant is the angel sent to help him get his priorities straight. Loretta Young is Niven's long suffering, and endlessly forgiving wife who is swept off her feet by the charming angel. The 'miracles' (1940s VFX) are a delight to watch and Cary Grant annoying David Niven is just perfect.

Festiv-o-meter: 8/10, Religiosity: High, but Cary Grant makes it charming Children: Medium, Animals: Safe and sound, they have an adorable St Bernard Costumes: Good

Please enjoy this very casual and not at all scripted anti-spoiler trailer

12. The Cheaters (1945)

The plot- convoluted but fun. A cliché wealthy family, plus an alcoholic theatre has-been, and a struggling show girl end up spending Christmas together in a secluded cottage and learn the true meaning of Christmas.

Festiv-o-meter: 9/10, Religiosity: Low, Children: Low, Animals: Safe and Sound, Costumes: Good

13. It Happened on Fifth Avenue (1947)

A ragtag bunch of people and an adorable dog called Sammy live the high life by spending Christmas in a temporarily abandoned mansion. Very funny and festive throughout.

Festiv-o-meter: 8/10, Religiosity: Low, Children: Low, Animals: Safe and sound- sammy is a very talented dog! Costumes: Good

14. Holiday Affair (1949)

This is not a particularly complicated film, but it brings the christmas cheer. Excellent film to have on while you sew last minute christmas outfits.

Festiv-o-meter: 7/10, Religiosity: Low, Children: Medium, Animals: Safe and Sound - contains some very good seals, Costumes: Good

15. Meet John Doe (1941)

Another rather prescient watch for 2024 about the role of journalism and the power of populism in America. Barbara Stanwyck plays a columnist facing redundancy who invents a letter from John Doe protesting the state of the world. It proves so popular that not only does she keep her job, she has to find someone to actually play John Doe for his adoring public. Mid way through the film there is what I can only describe as a fascist's motorcycle ballet, which really is quite something.

Festiv-o-meter: 3/10, Religiosity: Low- Medium at the end, Children: Low, Animals: Safe and Sound, Costumes: Good

16. It's a Wonderful Life (1946)

Probably the most traditional Christmas film there is. Quite heavy in places so definitely not a mindless romcom, but there are some funny moments. I'm glad I've seen it but it's not one I watch every year.

Festiv-o-meter: 6/10, Religiosity: High, Children: Medium, Animals: Safe and sound Costumes: Good

17. Beyond Tomorrow (1940)

A slightly supernatural story that starts with three wealthy old men conducting a social experiment to see who will return their three wallets on Christmas Eve. Two young people succeed and join them for Christmas dinner, and the old men end up supervising the young couple's romance from beyond the grave. A nice mix of drama, romance, and comedy.

Festiv-o-meter: 2/10, Religiosity: Medium, Children: Low, Animals: Safe and Sound, Costumes: Good

18. The Holly and The Ivy (1952)

Some British representation at last and it's pretty bleak, but very christmas-centric. The patriarch of the family is a parson so the religiosity is high in this one but it doesn't go unchallenged.

Festiv-o-meter: 8/10, Religiosity: High Children: Medium, Animals: Safe and sound Costumes: Good

19. The Lemon Drop Kid (1951)

A very Bob Hope film with very Bob Hope humour. Some fun bits but also a bit of a mess. Edith head did the costumes so they are very good.

Festiv-o-meter: 7/10, Religiosity: Low Children: Low, Animals: Safe and sound Costumes: Great.

20. Meet Me in St Louis (1944)

I love some things about this film but really dislike others. It's divided into 4 seasons starting in summer 1903. There are some cute moments in the other bits but my honest recommendation is just watch the winter 1903 section where you get to see a hilarious ballroom scene and Judy singing 'Have Yourself a Merry Little Christmas', and you can avoid the animal stuff and the weird Halloween bit.

The costumes and styling are a pretty interesting mix of 1940s and 1900s, and they do not hold back on colour, which is really fun. I love Judy's red dress so much and the lace and ribbon details on on the chemises and corsets are great.

Festiv-o-meter: 3/10, Religiosity: Low, Children: High, lots of crying, Animals: No actual animals are hurt but there are 2 places where harming cats is discussed and one dog moment that ends up being fine Costumes: Sensationally weird

21. Bachelor Mother (1939)

I love David Niven in comedies, and when you pair him with Ginger Rodgers and classic old man, Charles Coburn, this is really good. The only reason it's so far down the list is it just doesn't feel much like a Christmas movie to me so I wouldn't recommend it in that category. This story was remade into another not very christmassy film called Bundle of Joy in 1956.

Festiv-o-meter: 5/10, Religiosity: Low Children: Medium, Animals: Safe and sound Costumes: Good

22. Christmas Holiday (1944)

This film's title is a technicality, as the majority of the story has absolutely nothing to do with Christmas. A young soldier gets stranded on Christmas leave in New Orleans and befriends a nightclub singer whose husband is a charismatic murderer played by Gene Kelly. The NOLA architecture is really special and it's interesting to see gene kelly not pay a dancer, but this film isn't bringing the Christmas vibes you're probably looking for.

Festiv-o-meter: 1/10, Religiosity: Low, except one very intense church service near the start, Children: Low, Animals: Safe and Sound, Costumes: Good

23. We're No Angels (1955)

Humphrey Bogart in a prison-break buddy film comedy is quite the experience. This film was released in 1955 but set in 1895 so the costumes are a rather quirky mix. Overall a fun time. Not to be confused with the 1989 remake set in 1935 with exactly the same name where Robert DeNiro and Sean Penn escape prison and try to hide out in a monastery.

Festiv-o-meter: 7/10, Religiosity: Low, Children: Low, Animals: Safe and sound Costumes: Interesting

24. A Dream for Christmas (1973)

Okay yes it was a made for TV movie from 1973, but it's about Christmas, the cast isn't white, and it's set in 1950, SO IT'S GOING ON THE LIST. A pastor from the south is assigned to a poor church in California, the true meaning of Christmas ensues.

Festiv-o-meter: 6/10, Religiosity: High, Children: High, Animals: Safe and Sound, Costumes: They tried.

25. The Bells of St Mary's (1945)

Not very christmassy but happens partially over Christmas. Great if you liked the hot priest in fleabag.

Festiv-o-meter: 2/10, Religiosity: High, Children: Medium, Animals: Safe and Sound - fun bit near the start starring a cat in a hat, Costumes: Good

26. Miracle on 34th Street (1947)

A classic of the genre, an entire film deciding if Santa is real or not. A kid-centric drama/comedy set in New York between thanksgiving and Christmas. Maureen O'Hara's hair is very good throughout.

Festiv-o-meter: 9/10, Religiosity: Medium Children: High, Animals: Safe and sound Costumes: Good

27. Scrooge/A Christmas Carol (1951)

For a lot of people this is THE canonical Christmas Carol film and I can see why. Another British contribution here with pretty good 1840s costumes.

Festiv-o-meter: 8/10, Religiosity: Medium Children: Medium, Animals: Safe and sound Costumes: Good

28. Holiday Inn (1942)

Look, just watch White Christmas, they're basically the same and it's not worth it with this one. Some of the dance numbers are great and a holiday themed hotel is a very fun idea, but this movie is totally eclipsed by the blackface number and the fact they have a brilliant actor like Louise Beavers joining in from the sidelines with her two kids like it's no big deal.

Festiv-o-meter: 7/10, Religiosity: Low Children: Low, Animals: Safe and sound Costumes: Great