1. Holiday Inn (1942, starring Bing Crosby, Fred Astaire)
This musical features the best selling hit song White Christmas, and it was for this film that it was it was originally penned. Jim Hardy (Crosby) wants to get out of show business and have a relaxing life on a farm. His fiancee Lila (Virginia Dale), doesn't feel the same way and instead parters up with his friend Ted Hanover (Astaire). Things continue to go downhill for Jim in his new life until he decides to turn his farmhouse into the Holiday Inn, open for performances on holidays only, and meets Linda (Marjorie Reynolds). Forever chasing the good things Jim has, Ted show up at the Inn and attempts to steal Linda away. Backfiring double crosses and great musical numbers climax with a moving sentimental reunion of lovers and a happy ending.
2. Christmas In Connecticut (1945, Barbara Stanwyck, Sydney Greenstreet)
Barbara Stanwyck brings oodles of charm to this story of charades and shenanigans. A very successful writer, Elizabeth Lane works for a publisher who insists on his writers writing the absolute truth; unfortunately, Lane has painted herself as a wonderful chef, wife and mother with an amazing country life and has infact, no relation to any of those things. Employing the help of her many friends when her Christmas dinner-hungry boss invites himself over for the holidays, Lane finds herself trapped in an increasingly complicated facade, which includes a marriage proposal she has relentlessly tried to reject and pining for a handsome surprise guest.
3. The Man Who Came to Dinner (1945, Monty Woolley, Bette Davis, Ann Sheridan)
Acerbic dialogue fills this 1945 screen adaptation of the play. Radio personality Sheridan Whiteside's name is synonymous with Christmas, and when he slips on the steps of a family's home he becomes confined to their house under the assumption his leg is broken. Rumors abound that "Christmas may be postponed this year." He is either blithely worshipped or contemptuously loathed by all as he immediately assumes control of the entire house and its staff. His secretary Maggie (Davis) is the only one who seems to be a match for Whiteside, and the blows get a little out of hand when she falls in love with the local newspaperman, Burt Jefferson (Richard Travis).
4. Planes, Trains and Automobiles (1987, Steve Martin, John Candy)
One of the few successful modern holiday tales, this film is full of humor, both visual gags and biting lines. It showcases the best of John and Candy and Steve Martin. Nothing can go right for Neil Page (Martin) from the moment he tries to beat New York rush hour to get to the airport for a flight home to Chicago for Thanksgiving. At every turn, Neil finds himself with Del Griffith (Candy) by his side. Unwilling at first but eventually resigned to their paired traveling, things still continue to go awry, from a robbing to a broken down train to driving the wrong way down the highway. It's not just that everything that goes wrong does--it will do it in the worst way imaginable. A very poignant ending ties together the film; throughout, it's full of truly painful moments (unlike most comedies today that ring hollow and forced) and genuine sentiment.
5. The Lemon Drop Kid (1951, Bob Hope, Marilyn Maxwell)
Sidney Melbourne (Hope) is the Lemon Drop Kid, a well-known charming scam artist. Despite his reputation and penchant for being in trouble, a large number of his schemes seem to work. One day at the horse races, however, the Kid makes the fatal mistake of pulling one over on someone who works for Moose Moran, one of the biggest gangsters in town. He finds himself with having to replace the winnings or waking up Christmas morning "to find his head in his stocking." With the help of his friends and his gorgeous girl Brainy Baxter (Maxwell), the Kid attempts to pull off a scheme that would save his own neck but leave all his friends out in the cold. The movie has hilarious gags and a heartwarming ending and is the film responsible for bringing us "Silver Bells."
