“The Apartment” (1959)
Unrequited office crushes are the worst, especially when she is the mistress of the toxic boss to whom you sold out for an office on the 27th floor. Billy Wilder’s Best Picture winner starring Jack Lemmon and Shirley MacLaine has everything you didn’t know you wanted in a Christmas film: office politics, adultery and attempted suicide. But in this cold and cynical world of the takers vs. the taken, two lonely people find each other, and that’s an uplifting holiday message. Available on TCM’s app, Watch TCM. Also available for rent multiple places.
“Bell, Book & Candle” (1958)
The holidays are a swell time to fall in love. James Stewart is bewitched by Kim Novak, which stands to reason as she is a witch. What’s heartening about this holiday-set romantic comedy is the revelation that witches celebrate Christmas, too. Available on Criterion Channel.
“Comfort & Joy” (1984)
I take back what I said before: Holiday breakups are the worst. Glasgow radio DJ Dickie Bird (Bill Paterson) is devastated when his free-spirited girlfriend walks out, but he gets a new lease on life when he insinuates himself in the middle a rivalry between two ice cream companies. Bill Forsyth’s follow-up to his beloved “Local Hero” has that film’s off-center charms with a heartwarming Christmas message. It is unavailable to stream and out of print on home video, but you can find it on YouTube.
“The Lemon Drop Kid” (1951)
Bob Hope stars as the titular racetrack tout who has just 23 days until Christmas to come up with the $10,000 he owes mobster Moose Moran by hook or by crooked. Based on the Damon Runyan tale, one of Hope’s best comedies introduced the holiday standard, “Silver Bells.” If you can watch dry-eyed as block after block of Manhattan pedestrians sing along, you are made of sterner stuff than I am. Available for rent on Prime Video.
“The Man Who Came to Dinner” (1942)
‘Twas weeks before Christmas, and Sheridan Whiteside, world-renowned radio wit, is making life miserable for the unfortunate Ohio family in front of whose house he injured himself. Wheelchair-bound, he insults, thunders and makes impossible demands until finally, his unnerved nurse declares that she is quitting to find work in a munitions factory. “From now on,” she declares, “anything I can do to help exterminate the human race will fill me with the greatest of pleasure.” George Kaufman and Moss Hart’s classic comedy gets a rollicking screen adaptation with Monty Wooly recreating his iconic stage role (inspired by critic Alexander Wolcott), with Bette Davis as his long-suffering secretary, and Jimmy Durante as his Marxist (as in Harpo) prankster buddy. Available on HBO Max.