13 classic holiday films to watch with their modern Christmas counterparts
It’s the most wonderful time of the year — the time when you try to squeeze as many holiday movies into 25 days as is humanly possible.
Perhaps you have some festive viewing traditions, movies without which it’s not really Christmas. But maybe you’re also looking for something new? You’ve watched all the modern classics more times than you can count, and you’re looking for something that will satisfy your holiday thirst like a tall glass of eggnog.
The answer, of course, is to find yourself a Christmas throwback. If you’ve exhausted all the modern holiday movies, it’s time to turn back the clock to find something as cheerful and sentimental as your all-time favorites. To help you discern what to watch, we’ve compiled a list of 13 ideas for you: Find your favorite modern Christmas film, and we’ll suggest a perfect classic pairing. These movies go together better than Santa’s milk and cookies.
If you like Christmas With the Kranks (2004), watch Christmas in Connecticut (1945)
At first glance, these two films might not seem to have a lot in common, but ultimately they’re both Christmas farces that are all about celebrating the power of community. Both movies are predicated on passing off a lie to preserve the Christmas spirit. Christmas With the Kranks stars Jamie Lee Curtis and Tim Allen as Luther and Nora Krank. When the Kranks decide to skip Christmas with their daughter away, it invites the wrath of their community — until their daughter unexpectedly announces her arrival and they have to scramble to throw their annual Christmas party as if nothing ever happened. Similarly, in Christmas in Connecticut, Barbara Stanwyck portrays Elizabeth Lane, a wildly popular domestic columnist who actually knows nothing about homemaking despite the ruse that she lives in a Connecticut farmhouse with a loving husband and 8-month-old baby. Ordered by her PR team to host a wounded sailor for Christmas, Elizabeth has to come up with a Connecticut farmhouse good enough to fool the sailor and her unwitting publisher. Things get sticky as she tried to conceal her ineptitude and begins to develop feelings for the visiting sailor. Both films have plenty of holiday cheer, united in farcical attempts to decorate the house for Christmas. The image of Stanwyck decorating the tree while costar Dennis Morgan plays the piano is a lushly romantic and festive image that is the cherry on top of this hilarious holiday comedy.
If you like Home Alone (1990), watch We’re No Angels (1955)
Prefer your holidays with a side of home invasion? Have we got the double feature for you. The bumbling burglars of Home Alone, Harry (Joe Pesci) and Marv (Daniel Stern), have got nothing on the whimsical trio of Joseph (Humphrey Bogart), Albert (Aldo Ray), and Jules (Peter Ustinov), three escaped convicts who plan to murder a shopkeeper and his family and rob the place blind before being converted by the Christmas spirit. Both films toe the line between dark comedy and a real sense of the power of the holiday season to turn us all into kinder, more sentimental humans. Joseph, Albert, and Jules are less ridiculous and more menacing than Harry and Marv, but they equally humorous moments as they take this family under the wing and even make Christmas dinner. Pair the high jinks of Home Alone with the slightly more subtle humor of We’re No Angels.
If you like Love Actually (2003), watch Holiday Affair (1949)
Are you a fan of holiday films with a heavy side of romance and just a hint of melancholy? There’s probably no more beloved (or polarizing) modern holiday romance than Love Actually, and it pairs beautifully with this underrated gem about a war widow caught in a love triangle between a pragmatic lawyer and a rakish department store clerk. Janet Leigh is Connie, the widow who has turned her little boy into a sort of substitute husband in her grief. When she accidentally gets Steve (Robert Mitchum) fired from his holiday job, an unexpected romance strikes up between them. Leigh and Mitchum have buckets of chemistry, as much as any of the pairings in Love Actually. The added factor of her grief and the adorable concerns of her son, Timmy (Gordon Gebert), give it the necessary heft to tap into the more downbeat aspects of the holiday season that Love Actually tackles so brilliantly. The romance feels both as outsized and homespun as many of the Love Actually vignettes, veering from department stores to Connie’s modest apartment to a lunch date in front of the Central Park seals. And yes, it’s got a last-ditch effort grand gesture too — one to prove that love, actually, is all around.
If you like The Family Stone (2005), watch Remember the Night (1940)
A fish-out-of-water tale for the holidays is a source of endless delight, particularly when it ends in unexpected romance. Both The Family Stone and Remember the Night walk the line between drama and comedy and offer up a portrait of the challenges of navigating family dynamics around the holidays and finding love where you least expect it. Just as Meredith (Sarah Jessica Parker) finds herself thrust into the middle of the Stone family Christmas, so too does Barbara Stanwyck’s Lee get an unanticipated invitation to John Sargent’s (Fred MacMurray) home for the holidays. Lee is a shoplifter who’s been arrested and John is her prosecutor, but when he sees the unwelcome environment awaiting her at home, he takes her to his own much warmer house for the holidays. Both movies portray a formerly uptight or lost woman finding happiness in a messy, more idealized family. Lee gets to have the fantasy version of Christmas she’s always dreamed of, all the while falling in love with John, the man whose job it is to put her in prison. It’s perhaps even more inconvenient than Meredith falling for a different brother than the one she came home with in The Family Stone. If family dynamics at the holidays and a dose of genuinely heavy emotional moments all capped off with some moments of Christmas cheer is what you crave, this is a great double bill.
If you like The Santa Clause (1994), watch Miracle on 34th St. (1947)
Yes, we know there’s a modern remake of Miracle on 34th Street, but the original 1947 version is not only superior, it shares perhaps just as much of its DNA with another holiday original, 1994’s The Santa Clause. Both films are about parents and children of divorce trying to find their way back to the meaning of Christmas with the help of St. Nick. Both Charlie (Eric Lloyd) and Susan (Natalie Wood) are urged by their mothers to approach life, and Christmas, with a more grown-up view of reality — hence, a Christmas where there is no such thing as Santa Claus. In both cases, the real man in red, Kris Kringle (Edmund Gwenn) in Miracle and Charlie’s own dad, Scott (Tim Allen), in The Santa Clause, swoop in to restore some much-needed Christmas spirit (and avoid an insanity charge by those in their lives who also don’t believe in Santa). They both have one crucial lesson to offer: Besides Christmas spirit, family is what makes the holidays the most precious time of year. It’s silly, but we believe.
If you like Last Christmas (2019), watch The Bishop’s Wife (1947)
Need a little spiritual help for the holidays? Those who know Paul Feig’s love of Cary Grant perhaps could’ve guessed the central twist of Last Christmas — that Henry Golding’s Tom is not alive, but a spectral presence who gave his heart to Emilia Clarke’s Kate and has appeared to her as spirit to help her sort out her disaster of a life. Grant is an angel sent to Earth with the same purpose in The Bishop’s Wife. When a bishop, Henry (David Niven), loses sight of what matters, Dudley (Grant) enters his life to help get him back on track and fix his fractured marriage. The only trouble is that as Dudley spends more time with Julia (Loretta Young), the titular bishop’s wife, the two can’t help but develop a romantic tenderness for each other — just as Kate and Tom fall for each other in Last Christmas. The Bishop’s Wife, which was also remade as The Preacher’s Wife with Whitney Houston and Denzel Washington, is a beautiful ode to our need for little kindnesses in our life and how crucial it is to nurture those we love. Dudley makes all those he encounters feel valued and seen, an act especially crucial at Christmas, when the vulnerable can feel lonelier or more passed over than ever. If you’re in need of a beautiful love story that’s more about helping people find their way than it is about a passionate romance, The Bishop’s Wife will give you some angelic Christmas magic.
If you like The Best Man Holiday (2013), watch Meet Me in St. Louis (1944)
Looking for a holiday movie that uses Christmas as a backdrop but isn’t really all that related to the holiday? The Best Man Holiday and Meet Me in St. Louis both use the holiday as a crucial setting in places, but they’re ultimately more about togetherness than any one festive season. Both films are about family, the ones you’re born into and the ones you find for yourself. In The Best Man Holiday, a sequel to 1999’s The Best Man, a group of old friends gather for the holidays, exposing old wounds and new secrets as some relationships crumble and others spark. Similarly, the family unit is tested in Meet Me in St. Louis, when the Smith family patriarch declares he’s uprooting them all and moving to New York. Starring Judy Garland as Esther amid an ensemble cast as the rest of the Smith family and their various beaus, the movie was a perfect wartime parable for the struggle to keep the family unit together in difficult times. The Best Man Holiday delves into similar themes, while also using a similar lens to examine friendship. Not to mention, they both feature musical numbers: Meet Me in St. Louis throughout and The Best Man Holiday with an eye-catching lip-sync-and-dance session to “Can You Stand the Rain.” Both movies give you the chance to have yourself a merry little Christmas with plenty of drama and heart along the way.
If you like The Holiday (2006), watch It Happened on Fifth Avenue (1947)
House-swapping for the holidays can result in romantic bliss in both these holiday films. While the exchange between Iris (Kate Winslet) and Amanda (Cameron Diaz) in The Holiday is planned, the one in It Happened on Fifth Avenue is a bit more stealthy. Every Christmas, Aloysius T. McKeever (Victor Moore), a homeless man, moves into vacated Fifth Avenue mansions, emptied by rich snowbirds gone south for the winter. Only this time around, he’s joined by a recently evicted army veteran Jim (Don DeFore) and a whole host of other guests, such as Jim’s army buddies and the actual family that owns the house, including runaway heiress Trudy (Gale Storm) and her father in disguise as average folk. The film tackles everything from wealth disparity to budding romance to restoring relationships gone sour. In the end, it’s about how humanity’s greatest riches come in the form of friends and family, not untold wealth. Similarly, The Holiday uses the film’s two central romances, precipitated by the main characters deciding to shake up their lives, to interrogate their assumptions about love, family, and all the things that matter to them. If the uplifting holiday messages don’t win you over, the architecture porn will. Move in to a dream house for the holidays.
If you like Elf (2003), watch White Christmas (1954)
If you really, really, really love everything about Christmas — the lights, the cheer, the movies, the music, Santa Claus — this is an explosively festive double feature. White Christmas and Elf are both unapologetically earnest odes to the holiday season, celebrating everything that makes Christmas a special time of year. White Christmas does it with musical numbers, eye-catching in their Technicolor glory and bonkers production value. Elf does it with Will Ferrell’s infectiously joyous performance and sequences like decorating an entire department store DIY-style and getting an NYC crowd to sing Christmas carols. White Christmas follows Bob (Bing Crosby) and Phil (Danny Kaye), who, initially on a romantic mission alongside the Haynes sisters, Betty (Rosemary Clooney) and Judy (Vera-Ellen), end up at their old army commander’s Vermont inn. They resolve to put on a show to help bring money into the floundering inn and surprise the general to remind him how much his service meant to his men. In a way, it’s all about getting one old man to remember the value of the Christmas spirit and the love of those around him. And though Elf is a riotously funny tale of a man who believes himself an elf, it’s also about Buddy (Ferrell) trying to remind his father, Walter (James Caan), of much the same thing. In both cases, you walk away with the reminder that the best way to spread Christmas cheer is singing loud for all to hear (and that the best things also happen while you’re dancing).
If you like Carol (2015), watch All That Heaven Allows (1955)
Neither of these films are, in strictest terms, Christmas movies, but the holiday is crucial to their setting and the domestic drama/scandalous romance that makes up the heart of each film. They’re a natural pairing since Carol director Todd Haynes directly cites All That Heaven Allows and the work of director Douglas Sirk as a heavy influence on much of his filmmaking. The 1950s setting and themes of sexual repression and forbidden love run heavy through both pictures, and Carol’s boorish husband is played by Kyle Chandler, who even bears a striking resemblance to Sirk favorite Rock Hudson. Wealthy widow Cary Scott (Jane Wyman) falls for her much younger gardener, Ron Kirby (Hudson), much to the dismay of her children and officious neighbors. Both Heaven and Carol are tales of a taboo relationship that fights to beat the odds of societal disapproval (and even whispers of depravity and perversion). Sirk’s films always play as a metaphor for LGTBQ repression, and All That Heaven Allows even makes a few winking nods to Hudson’s own closeted sexuality. Carol simply brings that coded romance out in the open, using Patricia Highsmith’s The Price of Salt to craft a lesbian romance of the highest order. If you need some romantic longing and a good cry to go with your Christmas tree, this melodramatic double feature is for you. We like your hat.
If you like National Lampoon’s Christmas Vacation (1989), watch The Man Who Came to Dinner (1942)
Is there anything worse than unexpected house guests at the holidays? That’s the premise of both Christmas Vacation and The Man Who Came to Dinner, two films that inundate unsuspecting Midwestern families, the Griswolds and the Stanleys, with unwelcome visitors for the holiday season. The Griswolds have to face their own bickering parents and ignorant cousins. In The Man Who Came to Dinner, the Stanleys are beset by Sheridan Whiteside (Monty Woolley), an acerbic critic and radio personality who invites over a host of eccentric friends, including glamorous actress Lorraine Sheldon (Ann Sheridan), and installs his private secretary, Maggie (Bette Davis), as the head of the household. Havoc ensues as Maggie plans to leave her domineering boss’ employ for love and he plots to keep her in her position. It’s a holiday farce based on a Broadway play, one that hilariously captures much of the stress and emotional strain of the holidays, just like Christmas Vacation. It’s quite the lineup of Warner Bros. stars of the era, including Davis, Sheridan, and comic Jimmy Durante. If you like your holiday movies a little more harried and cynical, but still arriving at a celebration of the season, these two make a fine pair.
If you like I’ll Be Home for Christmas (1998), watch I’ll Be Seeing You (1944)
Who doesn’t love a Christmas road trip with a romantic element? I’ll Be Home for Christmas offers an epic and funny one as Jake (Jonathan Taylor Thomas) tries to make his way across the country to get home by Christmas Eve, so he can receive his father’s promised vintage Porsche. Along the way, he tries to win back his hometown girlfriend, Allie (Jessica Biel). I’ll Be Seeing You is a more somber but equally touching take on the journey. Mary (Ginger Rogers) and Zachary (Joseph Cotten) meet en route to the same town for Christmas, both carrying traumatic secrets. He’s a combat veteran being treated for PTSD, and she’s on leave from a prison sentence for manslaughter. While traveling together and over the course of the holiday season in the same town, they end up falling for one another. The film deals honestly with their vulnerabilities, crafting a sensitive romance that looks at their wounds with grace. Shirley Temple also costars as Mary’s niece in her first “grown-up” role (she was 16 while filming). It may seem like an odd pairing with the more tongue-in-cheek tale of a reformed cad that is I’ll Be Home for Christmas, but Jake is also recovering from emotional duress. The real reason he doesn’t want to go home for Christmas is because he hasn’t really spent much time at home since his mother died and his father remarried. Both these movies use the framework of returning home for the holidays as a way to explore some of the harder challenges of the season, while also leaving space for a touching romance.
If you like Die Hard (1988), watch 3 Godfathers (1948)
Prefer your Christmas movies with some heavy-duty action? Die Hard is the clear modern favorite for that, but the choices are more limited looking at the classics. 3 Godfathers comes closest, in some ways a traditional Western tale of outlaws on the run. John Wayne stars as Robert Marmaduke/Sangster Hightower, one of three bank robbers (Harry Carey Jr. and Pedro Armendariz are the other two) in this lesser-known John Ford title. The three rob a bank just days before Christmas, sending them on the run into the desert, but everything changes when they encounter a dying woman giving birth. They promise to see the child to safety in the town of New Jerusalem, guided there by a star. It is, of course, a metaphor, for the Biblical tale of the Three Wise Men. Besides the fact that they center on the top action heroes of their era, Willis and Wayne, the two films also share the common DNA of men trying to do the right thing in a dangerous situation at Christmastime against all odds. Die Hard even makes use of the myth of the American cowboy, with Willis’ John McClane earning comparisons to John Wayne from terrorist Hans Gruber (Alan Rickman). To this pairing, we say, “Yippee-ki-yay” — well, you know.
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