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The Shop Around the Corner (1940)
You'll probably recognize the plot of The Shop Around the Corner, because this Ernst Lubitsch film about warring shopworkers who are secret pen pals served as the inspiration for Nora Ephron's You've Got Mail. It culminates on Christmas Eve.
White Christmas (1954)
It's a perfect cinematic pairing when performing sisters (Rosemary Clooney and Vera-Ellen) team up with war buddies (Bing Crosby and Danny Kaye) for a grand show at a Vermont resort. Clooney's Betty and Crosby's Bob are resistant to coupling up, but their voices sound so good together, it only makes sense.
The Apartment (1960)
Billy Wilder's classic sets the standard for wild office holiday parties. C.C. Baxter (Jack Lemmon) hopelessly tries to flirt with Fran Kubelik (Shirley Maclaine) during the festivities. Unbeknownst to him, she's having an affair with Baxter's boss (Fred MacMurray), who has been using Baxter's apartment for rendezvous. Just wait until New Year's, C.C., then the tides will turn for you.
Rocky (Sylvester Stallone) and Adrian (Talia Shire) go on their ice skating date on Thanksgiving. It's awkward in the sweetest way. Their blooming love carries on throughout the holiday season.
Falling in Love (1984)
The central couple, played by Robert De Niro and Meryl Streep, meet while shopping in New York on Christmas Eve. The problem? They both happen to be married. A lovely, understated movie for grown-ups — the kind they just don't seem to make anymore.