You know Home Alone and Miracle on 34th Street and Love Actually and White Christmas, Elf and A Christmas Story and Die Hard and Christmas Vacation. But do you recall the most underrated holiday films of all? Okay, so saying they’re “the most underrated” might be a bit of an exaggeration. But the following eight titles are almost certainly not the first ones that come to mind for many people when the holidays roll around. For me, though, Christmastime isn’t complete until I cozy up with these little-known, little-discussed classics, so if you’re looking to expand your own holiday watchlist or you’re just in the mood for something heartwarming, silly, or both, this list is definitely for you.
Quick note: I tried to strike a balance of pre-1970 films and more modern ones, but as a classic film obsessive, my list, which by no means is complete, does skew a certain way. (And, to be frank, 97% of the modern holiday films I watch I wouldn’t consider underrated and I have a feeling you’d agree.) Hopefully this doesn’t deter you — after all, a good movie is a good movie!
Christmas in Connecticut (1945)
Over the past 10 years or so, I’ve been thrilled to witness the resurgence of Christmas in Connecticut in the classic film community. (It’s even been placed in AMC’s annual rotation alongside more familiar fare like Christmas Vacation.) A thoroughly delightful romantic comedy, Christmas in Connecticut is, to me, perfect. Touted as the world’s greatest cook and homemaker, Elizabeth Lane (Barbara Stanwyck) writes a column for Smart Housekeeping, one of many publications owned by Alexander Yardley (a guffawing Sydney Greenstreet). When Yardley asks Elizabeth to host war hero Jefferson Jones (Dennis Morgan) at her idyllic Connecticut farm for Christmas, there is just one problem: Elizabeth is not who she says she is.
There is a lot that makes this film special, including my favorite character actor, S.Z. “Cuddles” Sakall, but what really makes Christmas in Connecticut magical is Barbara Stanwyck’s hilarious performance and the way Elizabeth Lane subverts traditional gender roles. Instead of being the perfect housewife her column makes her out to be, Elizabeth is a single careerwoman who knows zilch about domestic matters and we love her for it. Her cluelessness is refreshingly modern, as is her obvious lust for Jefferson Jones. From the moment their characters lock eyes, Stanwyck and Dennis Morgan’s chemistry takes Christmas in Connecticut to another level, making it all the more enjoyable to revisit year after year.
Available on DVD, cable (TCM and AMC), and for rent on various streaming platforms like Amazon Prime Video and YouTube
I’ll Be Seeing You (1944)
A shellshocked soldier who is on leave from a hospital to try and adjust to daily life, Sgt. Zach Morgan (Joseph Cotten) is charmed when he meets Mary Marshall (Ginger Rogers) on a train that is taking her to her aunt and uncle’s for the holidays. What Zach doesn’t know, though, is that Mary is on furlough from a women’s prison where she must serve three more years for a manslaughter charge that really should’ve been seen as self-defense.
I’ll Be Seeing You is a melancholic film, and a fascinating critique on the brutality of war, but it is also about rediscovering hope and the strength you can find from love both familial and romantic. Rogers and Cotten’s exquisite performances let you feel their characters’ yearning for a “normal” existence, making their struggles all the more real and the happiness they’re reaching for all the more profound. Director William Dieterle was a brilliant craftsman, especially when it came to hauntingly beautiful dramas like his other two films with Cotten, Portrait of Jennie and Love Letters, and I’ll Be Seeing You is just another example of what a gifted artist he was.
Available on DVD and for rent on streaming platforms like Amazon Prime Video and YouTube
Is this film a masterpiece? No. Do I still grin like an idiot every time I watch it? You bet. To borrow a phrase from David Carter, Serendipity is a lost three-star gem of the early 2000s, one that will either charm or irritate you. Maybe I’m lowering your expectations too much, but I think that’s what helped me fall for this movie when I first saw it.
Kate Beckinsale and John Cusack play characters who meet one day while trying to buy the same pair of gloves at Bloomingdale’s during the Christmas rush. Although they are both in relationships, they wind up spending the evening together walking around New York City. Beckinsale is a firm believer in fate, but Cusack has his doubts. Their perspectives are tested when they go their separate ways only to realize a few years later, as both have become engaged to other people, that they still haven’t forgotten each other.
While the plot is pure, delicious cheese, Serendipity benefits from a pleasantly sweet script and a star-studded cast, including Molly Shannon as Beckinsale’s best friend, John Corbett as her fiancé, Bridget Moynahan as Cusack’s bride-to-be, and, my personal favorite, Eugene Levy as an oddball Bloomingdale’s clerk.
Available on DVD and to rent from various streaming platforms like Amazon Prime Video and YouTube
In the Good Old Summertime (1949)
While most people love to watch Meet Me in St. Louis this time of year, I prefer this other Judy Garland musical. A remake of Ernst Lubitsch’s masterpiece The Shop Around the Corner, which was also adapted as the Broadway show She Loves Me and Nora Ephron’s 1998 classic You’ve Got Mail, In the Good Old Summertime is probably the least well-remembered out of these many versions. On the one hand, it’s understandable. The songs are, for the most part, not super memorable, and the story is softened to help homogenize the film as one of MGM’s signature family-friendly flicks.
However, once you accept all that, In the Good Old Summertime is just as lovely as its more famous counterparts. Judy Garland is, as always, exceptional, and she is matched every step of the way by Van Johnson. The scene where Johnson seductively nuzzles against Garland as they confess their feelings for each other in hushed tones never fails to turn me into a pile of mush. The rest of the cast is great, too. Buster Keaton does wonders with a small supporting role; he additionally choreographed the film’s physical gags, including Garland and Johnson’s slapstick meet-cute. This movie is also the screen debut of a three-year-old Liza Minnelli!
Available on DVD, cable (TCM), and for rent on various streaming platforms like Amazon Prime Video and YouTube
Simon and Laura (1955)
When a BBC producer comes up with a TV show that follows the home life of a celebrity couple, he decides there is one perfect choice: Simon and Laura Foster (Peter Finch and Kay Kendall). What he doesn’t know, though, is that the Fosters have been at each other’s throats for years, their marriage rife with jealousy and insults. Desperate for the spotlight (and the income), Simon and Laura agree to the show and find new fame as reality TV stars. But just how long can they keep up the charade?
Directed by Muriel Box, who has been called Britain’s most prolific female director, Simon and Laura is brimming with delicious, biting dialogue, candy-colored hues, and amusing characters. It also offers a surprisingly still-relevant behind-the-scenes look at television, particularly the phoniness of reality shows. While only a holiday film peripherally — there is just one part, an epically disastrous taping of the Fosters’ program, that takes place on Christmas — Simon and Laura is ideal for those who like their holiday content to be a little more naughty than nice.
Available on DVD
While You Were Sleeping (1995)
Proof that every Christmas movie should have a dreamy, flannel-wearing Bill Pullman, While You Were Sleeping is quintessential holiday viewing. Sandra Bullock plays Lucy, a lonely transit worker who is smitten with Peter Callaghan (Peter Gallagher), a dashing stranger she has seen at her token booth for the past few months. After Peter is pushed onto the subway tracks and knocked unconscious, Lucy saves him from an oncoming train and is assumed to be his fiancée at the hospital where he has fallen into a coma. When his family — which includes Peter Boyle and the terrific Glynis Johns — welcomes her with open arms, Lucy is mortified but, as a woman who has felt crushingly alone following both of her parents’ deaths, she finds comfort in the Callaghans’ adorable bickering and genuine warmth. The charade gets more complicated, though, when Peter’s brother, Jack (Pullman), enters the picture.
While You Were Sleeping is probably the coziest movie on this list, and it’s not just because of the myriad of big, comfy sweaters everyone wears. The love Lucy begins to feel for the Callaghans is poignant in an authentic way, and the relationship that grows between her and Jack similarly radiates a sweetness that will make you smile until your face hurts. It’s easy to see why this was the film that made Sandra Bullock into a romantic-comedy star. Her performance is endearing and emotional without ever being cloying, allowing us to fully buy into the story as well as Lucy’s reluctance to tell the Callaghans the truth.
Available on DVD, Disney+, and for rent on various streaming platforms like Amazon Prime Video and YouTube
Dick Van Dyke is Fitzwilly, a devoted butler who secretly leads his fellow servants in larceny to support the philanthropy of their beloved elderly employer, Miss Vicki (Edith Evans). When Barbara Feldon shows up as Miss Vicki’s new secretary, she begins to suspect that something isn’t quite right… Can Van Dyke distract her from what’s really going on? And will the servants be able to pull off their last big heist?
This charming ’60s romp is a big favorite of mine. The premise is fun; Feldon’s fashion choices make me drool; the score is by a young John Williams; every single character is interesting and distinctive, and they’re all played by such wonderful actors as Norman Fell, Sam Waterston, John McGiver, and Cecil Kellaway. The film does a fine job of balancing its sentimentality and cynicism, and watching Feldon match wits with Van Dyke is pure joy.
Available on Amazon Prime Video, DVD, and cable (TCM)
Happy Holidays with Bing and Frank (1957)
Alright, this is actually a TV special. And it’s not exactly a great one. Directed by Frank Sinatra, this 26-minute show features Ol’ Blue Eyes and his two-time co-star Bing Crosby crooning one yuletide classic after another. Although the script is filled with corny dialogue, the atmosphere is a touch too rigid, and Sinatra’s performance feels especially awkward when placed next to Crosby’s easy, breezy demeanor — as Tom Santopietro wrote in Sinatra in Hollywood, “It’s as if Sinatra’s impatience with the medium, an impatience that at its worst translated as contempt, came through more clearly on the small screen than in any of his singing or movie roles” — this imperfect slice of ’50s live television has become a staple of my holiday line-up. In fact, I think I love it more because of its flaws. It’s fun seeing Crosby bust Sinatra up during a duet of “Jingle Bells” and watching Sinatra’s real-time reaction when he is singing “Mistletoe and Holly” (a fantastic song he co-wrote) while decorating a tree and he accidentally drops an ornament. And yes, I do love that terrible banter.
Available on DVD and in full on Vimeo
I’ll be gushing about another underrated holiday favorite as part of this month’s Monthly Movie Round-Up, which will be presented LIVE as a virtual event on December 15. Register now to join me and rest of the blogging team for what’s sure to be a fun conversation!
Michaela Owens is thrilled to be the editor of A Place for Film, in addition to being IU Cinema’s Publications Editor. An IU graduate with a BA in Communication and Culture and an MA in Cinema and Media Studies, she has also been a volunteer usher at IU Cinema since 2016. She never stops thinking about classic Hollywood, thanks to her mother’s introduction to it, and she likes to believe she is an expert on Katharine Hepburn and Esther Williams.