The 30 Best Old Hollywood Christmas Movies of All Time

It’s a Wonderful Life, Christmas in Connecticut, Miracle on 34th Street, and more!

Old Hollywood created some of the best Christmas movies of all time. When the winter holidays roll around, so many people put on It’s a Wonderful Life, Holiday Affair, or The Shop Around the Corner. These comfort movies have stood the test of time and remain the favorites of so many!

Below, we’ve ranked the 32 best classic Old Hollywood Christmas movies of all time. Every film on this list is delightful and highly watchable. We’ve included some of the big films that we all know and love. However, we’ve also tried to add some underrated gems that we feel people will enjoy! 

Now, all of these movies below revolve around Christmas in some way. In some films, the entire plot revolves around Christmas. In other films, it’s present, but maybe not so evident. Regardless, all of the movies here revolve around Christmas and the winter season in some way! 

So, if you’re looking for the best classic Old Hollywood Christmas movies, look no further. Use this list as a handy guide this winter to watch some comfort classics! 

The 30 Best Classic Old Hollywood Christmas Movies, Ranked

30. The Cheaters (1945)

Genre: Romance / Comedy / Drama

Starring: Joseph Schildkraut, Billie Burke, Eugene Pallette, Ona Munson

Directed by: Joseph Kane

Up first, we’ve got 1945’s The Cheaters. Throughout the 1960s and 1970s, this Christmas movie was shown during the winter holidays, making it a constant for so many during this time. So, while not the absolute best classic Old Hollywood Christmas movie, we couldn’t make this list without including it! 

The Cheaters follows an aristocrat struggling with money. He believes that his uncle’s dying fortune will help him. However, as he tries to learn who the heir to his uncle’s fortune is, his family takes in an alcoholic ex-actor for the holidays — and this man definitely complicates things. It’s a joy to watch! 

The Cheaters is definitely a bit of an underrated gem compared to the other films on this list. But if you’re looking for something new (that’s very old) to watch this winter, put this movie on! 

29. Susan Slept Here (1954)

Genre: Comedy / Drama

Starring: Dick Powell, Debbie Reynolds, Anne Francis, Glenda Farrell

Directed by: Frank Tashlin

In Susan Slept Here, Dick Powell lets a rebellious young lady (Reynolds) stay with him, and he promises to look out for her, as he’s doing a study on juvenile delinquency. However, this young lady causes an awful lot of problems. And everything is placed during the Christmas holidays, which makes the whole thing even better! 

Related — Debbie Reynolds: 9 Essential 1950s Movies

28. Christmas Holiday (1944)

Genre: Film Noir / Crime / Drama

Starring: Deanna Durbin, Gene Kelly, Richard Whorf, Dean Harens

Directed by: Robert Siodmak

If you’d like a film noir to watch this winter, check out the underrated Christmas Holiday, which is definitely one of the best classic Old Hollywood Christmas movies! 

In this 1944 film, a New Orleans nightclub singer (Durbin) tells a soldier the tragic tale of her marriage to a scoundrel (Kelly). It’s definitely riveting to watch! 

Related — The Best Gene Kelly Musicals of All Time

27. The Great Rupert (1950)

Genre: Comedy

Starring: Jimmy Durante, Terry Moore, Tom Drake, Frank Orth

Directed by: Irving Pichel

The Great Rupert is another underrated Christmas classic gem! In this comedy, an impoverished former vaudeville performer and his wife and daughter get a room at a house, even though they don’t know how they’ll pay the rent. However, when a squirrel becomes the guardian angel for the family and subsequently gets them money, things change! 

26. Beyond Tomorrow (1940)

Genre: Fantasy / Romance / Drama

Starring: Harry Carey, C. Aubrey Smith, Charles Winninger, Alex Melesh

Directed by: A. Edward Sutherland

Beyond Tomorrow is also one of the best classic Old Hollywood Christmas movies! In this fantasy film, three ghosts try to smooth the way for a young couple they knew during their lifetime. It’s a marvelous film! 

25. Scrooge (1935)

Genre: Fantasy / Drama

Starring: Seymour Hicks, Donald Calthrop, Robert Cochran, Mary Glynne

Directed by: Henry Edwards

You don’t want to sleep on 1935’s Scrooge. In this fantasy, we follow the iconic Ebenezer Scrooge as he is visited by various visions. And along the way, he learns the true meaning of Christmas! 

24. All Mine to Give (1957)

Genre: Romance / Drama

Starring: Glynis Johns, Cameron Mitchell, Rex Thompson, Patty McCormack

Directed by: Allen Reisner

Set in the 1850s, All Mine to Give follows a large family as they immigrate from Scotland to the American Midwest. However, when the parents of the family die, the children band together as they try to survive and better their lives. 

23. Sun Valley Serenade (1941)

Genre: Comedy

Starring: Sonja Henie, John Payne, Glenn Miller, Milton Berle

Directed by: H. Bruce Humberstone

In Sun Valley Serenade, a bandleader and his group decide to adopt a war refugee to gain some publicity. Instead of getting a child, they end up with a beautiful young woman! As the group heads to snowy Idaho for a gig, we get a lot of lovely numbers in the snowy weather! 

22. The Lemon Drop Kid (1951)

Genre: Music / Crime / Comedy

Starring: Bob Hope, Marilyn Maxwell, Lloyd Nolan, Jane Darwell

Directed by: Sidney Lanfield

The Lemon Drop Kid is also one of the best classic Old Hollywood Christmas movies! In this fun 1951 film, Bob Hope plays a bookie who has until Christmastime to pay back a gangster, as he owes him for a bad tip! 

21. Going My Way (1944)

Genre: Music / Comedy / Drama

Starring: Bing Crosby, Barry Fitzgerald, Frank McHugh, James Brown

Directed by: Leo McCarey

In Going My Way, we have the King of Christmas Music himself, Mr. Bing Crosby! That’s always a joy! As a result, Going My Way is often considered one of the best classic Old Hollywood Christmas movies of all time — and we can’t help but agree! 

In this film, Crosby plays a likable young priest who comes to a new parish. He ends up helping to revitalize the failing parish. He even gets the elder priest (Fitzgerald) who doesn’t like or trust him at first to come around! A lovely Christmas movie! 

Related — The Top 10 Best Bing Crosby Christmas Songs

20. The Holly and the Ivy (1952)

Genre: Drama

Starring: Ralph Richardson, Celia Johnson, Margaret Leighton, Denholm Elliott

Directed by: George More O’Ferrall

The Holly and the Ivy is an amazing, heartbreaking British Christmas classic. In this 1952 film, a family that was torn apart by World War II reunites for the Christmas holidays — and it is both riveting and heartbreaking to watch. 

19. I’ll Be Seeing You (1944)

Genre: Romance / Drama

Starring: Ginger Rogers, Joseph Cotten, Shirley Temple, Spring Byington

Directed by: William Dieterle

If you’d like a tragic romantic drama to watch this winter, check out I’ll Be Seeing You, which is definitely one of the best classic Old Hollywood Christmas movies! In this 1944 drama, Rogers and Cotten play two people who meet on a train and have a mutual attraction for each other. 

However, they both also have their own secrets. He’s a wounded war vet, while she’s on leave from prison for the Christmas holidays. How can a romance bloom when they are both hiding so much? A must-watch! 

Related — Joseph Cotten: 13 Essential 1940s Movies

18. March of the Wooden Soldiers (1934)

Genre: Fantasy / Comedy

Starring: Stan Laurel, Oliver Hardy, Virginia Karns, Charlotte Henry

Directed by: Gus Meins, Charley Rogers 

March of the Wooden Soldiers, also called Babes in Toyland, follows two employees of a toymaker who try to find and borrow money. They need money to help Mother Peep pay the mortgage of her shoe! A great, classic film that’s so fun to watch! 

17. Holiday Affair (1949)

Genre: Comedy / Drama

Starring: Robert Mitchum, Janet Leigh, Wendell Corey, Gordon Gebert

Directed by: Don Hartman

Alright, folks. Now we’re getting to THE classics. Holiday Affair is definitely one of the best classic Old Hollywood Christmas movies of all time. Its place here, somewhat low on this list, even surprised us, as it’s excellent! But that just goes to show you how many other great classic Christmas films there are! 

In Holiday Affair, a seasonal sales clerk (Mitchum) catches a woman (Leigh) shoplifting during the Christmas shopping rush. However, he lets her go — and is subsequently fired on the spot. The two end up getting to know each other, and when he learns that she’s a mother and a war widow, he begins to see her in a different light. However, she is engaged to marry another… so, this film has a lot of fun Christmas drama! 

16. The Bells of St. Mary’s (1945)

Genre: Drama

Starring: Bing Crosby, Ingrid Bergman, Henry Travers, William Gargan

Directed by: Leo McCarey

We’ve got another Bing Crosby movie! This time, he’s paired with the iconic Ingrid Bergman. In The Bells of St. Mary’s, a liberal priest (Crosby) is transferred to an inner city school where he immediately butts heads with the strict headmistress (Bergman). However, eventually, the two see eye to eye and learn how to work together! 

Related — The Top 10 Best Ingrid Bergman Movies of All Time

15. Remember the Night (1940)

Genre: Romance / Comedy / Drama

Starring: Barbara Stanwyck, Fred MacMurray, Beulah Bondi, Elizabeth Patterson

Directed by: Mitchell Leisen

Goodness, do we love Remember the Night here at Retro Gazing. Definitely one of the best classic Old Hollywood Christmas movies of all time! And, it’s the first Barbara Stanwyck film we have here on this list. Don’t worry, we’ll have plenty more later! 

Remember the Night follows a district attorney (MacMurray) who, in the Christmas spirit, lets a shoplifter (Stanwyck) out for the holidays. The two end up riding home to Indiana together — and subsequently falling in love, even though they know they can never be. A wonderful film! 

Related — Barbara Stanwyck and Fred MacMurray Movie Collaborations, Ranked

14. Holiday Inn (1942)

Genre: Music / Comedy / Drama

Starring: Bing Crosby, Fred Astaire, Marjorie Reynolds, Virginia Dale

Directed by: Mark Sandrich, Robert Allen 

Aaaand we’ve got another Bing Crosby Christmas classic! This time, he’s paired with Fred Astaire… need we say more? Instant classic! 

In Holiday Inn, Crosby plays a song and dance man who, after facing heartbreak, retires and opens a country inn — an inn that has a holidays-only live entertainment venue! However, when his old friend — and foe — shows up and possibly causes romantic turmoil, chaos ensues. And boy, is it fun to watch! 

13. It Happened on Fifth Avenue (1947)

Genre: Music / Romance / Comedy

Starring: Don DeFore, Ann Harding, Charles Ruggles, Victor Moore

Directed by: Roy Del Ruth

It Happened on Fifth Avenue is also one of the best classic Old Hollywood Christmas movies! It’s such a delight. It Happened on Fifth Avenue follows two drifters who squat in a rich man’s home while he’s vacationing in the South. However, when the rich man’s daughter arrives, she falls in love with one of them! 

12. We’re No Angels (1955)

Genre: Crime / Romance / Comedy

Starring: Humphrey Bogart, Peter Ustinov, Aldo Ray, Joan Bennett

Directed by: Michael Curtiz

This Christmas, why not put on a Humphrey Bogart film? In We’re No Angels, Bogart and his two cohorts escape from prison and hide out in a shop run by a kindhearted family. Though the criminals at first plan to steal from them and then run, they change their minds once they eat a Christmas dinner with them. 

Then, the three decide to help the family out and possibly do a few good deeds — especially when they learn about the financial trouble the family is in. A great classic to watch! 

Related — The Top 10 Best Humphrey Bogart Movies of All Time

11. Christmas in Connecticut (1945)

Genre: Romance / Comedy

Starring: Barbara Stanwyck, Dennis Morgan, Sydney Greenstreet, Reginald Gardiner

Directed by: Peter Godfrey

Here’s another Stanwyck pick! This list of the best classic Old Hollywood Christmas movies wouldn’t be complete without Christmas in Connecticut, would it? 

This movie is wonderful! Stanwyck plays a homemaking specialist who, in reality, can’t even boil water. She’s not married, nor does she have a child — nor does she live on a farm. However, she writes that she does! 

When a war hero is recovering in a hospital, he grows fond of her column, and his nurse arranges with the publisher to allow him to spend the holidays with Stanwyck’s fake homemaker. So, the publisher works to set up this sham lifestyle… though who knew love would blossom between the columnist and the war hero? An instant classic! 

Related — The 11 Best Barbara Stanwyck Movies From the 1940s

10. The Man Who Came to Dinner (1942)

Genre: Romance / Comedy

Starring: Bette Davis, Ann Sheridan, Monty Woolley, Richard Travis

Directed by: William Keighley

And now, for those who always feel they need a little bit of Bette Davis in their lives. The Man Who Came to Dinner is also one of the best classic Old Hollywood Christmas movies of all time! How could it not be?

In this great comedy, an opinionated radio personality (Woolley) falls and injures himself while on a speaking tour in Ohio, forcing him to shack up with a prominent family in two for the winter. Of course, this doesn’t exactly go over well, and he causes chaos all around him! 

Related — The Top 10 Best Bette Davis Movies of All Time

9. A Christmas Carol (1938)

Genre: Fantasy / Drama

Starring: Reginald Owen, Gene Lockhart, Kathleen Lockhart, Terry Kilburn

Directed by: Edwin L. Marin

A Christmas Carol has been done a few times before, as you can see by this list. However, 1938’s really is something special — and is, therefore, one of the best classic Old Hollywood Christmas movies to watch during the winter holidays! 

This fantasy movie follows the classic story of Ebenezer Scrooge that we all know and love. In this Charles Dickens story, Scrooge is visited by ghosts and apparitions during the Christmas holidays, showing him what real holiday spirit looks like — and helping him change his grouchy, rude ways! 

8. Meet Me in St. Louis (1944)

Genre: Musical / Comedy / Drama

Starring: Judy Garland, Margaret O’Brien, Mary Astor, Lucille Bremer

Directed by: Vincente Minnelli

Meet Me in St. Louis actually takes place covering a whole year of four sisters in St. Louis as they await the 1904 St. Louis World’s Fair. Christmas is a big part of this film — but not the entire part. Regardless, so many people consider this one of the best Old Hollywood Christmas movies, and we cannot help but agree! 

Related — The Top 10 Best Judy Garland Movies of All Time

7. White Christmas (1954)

Genre: Musical / Romance / Comedy

Starring: Bing Crosby, Danny Kaye, Rosemary Clooney, Vera-Ellen

Directed by: Michael Curtiz

We’ve got another Bing Crosby film! It’s hard not to love this musical. White Christmas follows two musical stars (Crosby and Kaye) who team up with a sister act (Clooney and Vera-Ellen) to set up a show to help out the men’s former military commander who has fallen into financial difficulties. A great film! 

6. Meet John Doe (1941)

Genre: Romance / Comedy / Drama

Starring: Gary Cooper, Barbara Stanwyck, Edward Arnold, Walter Brennan

Directed by: Frank Capra

Meet John Doe’s entire movie leads up to Christmas — and it’s definitely one of the best classic Old Hollywood Christmas movies to watch! Frank Capra can do no wrong, in our eyes. 

In Meet John Doe, Stanwyck plays a journalist who, upon being fired, writes a column pretending to be John Doe, a man threatening to kill himself on Christmas because of the injustices and cruelties of the world. When everyone in town rushes to this fake man’s aid, she returns to work and hires a bum (Cooper) to pretend to be this man. 

However, things escalate out of control when John Doe starts a real movement for working-class people, as he begins to worry that he’s being controlled by a rich oil man. This movie really is amazing and we highly recommend it!  

Related – Barbara Stanwyck and Gary Cooper Movie Collaborations, Ranked

5. The Bishop’s Wife (1947)

Genre: Fantasy / Comedy / Drama

Starring: Cary Grant, Loretta Young, David Niven, Monty Woolley

Directed by: Henry Koster

The Bishop’s Wife is another great feel-good movie to watch during the winter holidays! Who doesn’t like seeing this all-star cast together on the screen? 

In The Bishop’s Wife, Cary Grant plays an angel who comes down to Earth to help a bishop (Niven) and his wife (Young) who are facing difficulties as they try to build a new cathedral in town. A wonderful Christmas classic that truly never gets old! 

Related — Cary Grant: Top 10 Best 1940s Movies

4. A Christmas Carol (1951)

Genre: Fantasy / Drama

Starring: Alastair Sim, Jack Warner, Kathleen Harrison, Mervyn Johns

Directed by: Brian Desmond Hurst

In our opinion, 1951’s A Christmas Carol is the best adaptation of Ebenezer Scrooge’s story around! It’s also one of the best classic Old Hollywood Christmas movies of all time! 

In A Christmas Carol, also called Scrooge, Ebenezer Scrooge is visited by a ghost and other apparitions on Christmas as they teach him to right his wrongs. A great version! 

3. The Shop Around the Corner (1940)

Genre: Romance / Comedy / Drama

Starring: Margaret Sullavan, James Stewart, Frank Morgan, Joseph Schildkraut

Directed by: Ernst Lubitsch

The Shop Around the Corner is also one of the best classic Old Hollywood Christmas movies of all time! If you’d like a lovely romance to watch this winter, put this movie on! 

In The Shop Around the Corner, Stewart and Sullavan play two feuding workers at a general store in Budapest around Christmastime. The two have fallen in love with their pen pals — and have no idea that they’re each other’s pen pals! They’ve unknowingly fallen in love with each other! 

Related — James Stewart and Margaret Sullavan Movie Collaborations, Ranked

2. Miracle on 34th Street (1947)

Genre: Comedy / Drama

Starring: Edmund Gwenn, Maureen O’Hara, John Payne, Gene Lockhart

Directed by: George Seaton

Miracle on 34th Street is SUCH a great film. Truly one of the best classic Old Hollywood Christmas movies of all time! If you’re looking for a movie to put you in the Christmas spirit, you really should watch this film. 

Miracle on 34th Street follows a man named Kris Kringle (Gwenn) who is a department store Santa. When he proclaims that he is the real Santa Claus, he faces disbelief — and questions of sanity — from all. A wonderful movie! 

1. It’s a Wonderful Life (1946)

Genre: Fantasy / Drama

Starring: James Stewart, Donna Reed, Lionel Barrymore, Thomas Mitchell

Directed by: Frank Capra

It’s a Wonderful Life is the best classic Old Hollywood Christmas movie of all time. It’s simply phenomenal. If you’ve never seen this feel-good classic, watch it as soon as you can! 

In It’s a Wonderful Life, Stewart plays George Bailey, a man who believes it would be better for everyone if he was never born. On Christmas, an angel comes down and shows him what life would’ve been like if he had never been born — and it’s not great. 

Truly a phenomenal film that should be watched by everyone! 

Related — The Top 10 Best James Stewart Movies of All Time

Comment below your own favorite classic movie to watch during the winter holidays! Do you agree with this list? Or would you change things up a bit? Hit the comments below with all your thoughts and opinions! I’d love to hear what you think! 

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