Holiday Inn (1942): Bing stars with Fred Astaire as former song and dance partners who have a nasty habit of chasing the same women. After Bing moves to Connecticut to open a themed boutique hotel which is only open on national holidays, a.k.a. "Holiday Inn," the two men reluctantly reunite. Though it takes place over the course of a year, with a musical number for each holiday, Holiday Inn really feels like a Christmas movie because it introduced the now-classic carol "White Christmas" by Irving Berlin.
White Christmas (1954): Bing and Danny Kaye play Army buddies turned successful entertainers who follow a sister act (Rosemary Clooney and Vera Ellen) to Vermont during an unseasonably warm winter. Vera Ellen is one of my favorite dancing ladies and when she teams with Danny Kaye for "The Best Things Happen While You're Dancing," it is pure joy.
And speaking of that song...it's interesting to see how differently "White Christmas" is treated in Holiday Inn and this film which shares its title. In Holiday Inn, the song is melancholy, sung by a man who is lonely at Christmas. Twelve years later, the song has become a standard. When it is performed by Bing and the rest of the cast (at the beginnning and at the finale) it's no longer a lament, but an expression of nostalgia.
Going My Way (1944) and The Bells of St. Mary's (1945): Bing portrays Father O'Malley, the newly arrived priest who shakes things up at a failing parish. The delightful Barry Fitzgerald plays an old-fashioned elder priest. In 1944, Going My Way was awarded Oscars for Best Picture, Best Director (Leo McCarey), Best Actor (Bing Crosby), Best Supporting Actor (Barry Fitzgerald), Best Song ("Swingin' on a Star"), as well as two other awards.
This film was so popular it warranted a sequel the next year, The Bells of St. Mary's. This time, liberal Father O'Malley finds himself butting heads with strict nun Ingrid Bergman (also an Oscar winner in 1944 for Gaslight) over how best to run the St. Mary's school.
Again, these films do not take place exclusively during the holidays; however, the "holiday spirit" is at the core of each one. The stories may seem corny to "modern" audiences, but I contend that if you can't enjoy these two sweet films then you have no heart.
AMC is showing Holiday Inn during December (check listings on http://www.amctv.com/) and a White Christmas marathon on Christmas Eve. Unfortunately, I couldn't find any scheduled showings of Going My Way or The Bells of St. Mary's this month. However, all four of these films are available on DVD.
Happy Holidays!
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