Holiday Inn (not rated)
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This came out in 1942 (33 years before I was born). I first saw it on Christmas in 2016, after having intended to buy the DVD for the past few years or so. It's not... exactly... a Christmas movie, though the holiday does bookend the film. I'd also say it's not exactly a musical, since it always makes sense for people to sing the songs they do, when they do. So, whatever, I'll just list it under "classics"... and I guess "miscellaneous holidays."
There's this entertainment team consisting of a singer named Jim Hardy (Bing Crosby), a dancer named Ted Hanover (Fred Astaire), and a woman who both sings and dances named Lila Dixon (Virginia Dale). Lila is engaged to Jim, who wants to leave the act and become a farmer. However, Lila doesn't want to go with him. Instead, she stays with Ted, and breaks off her engagement to Jim. Over the course of the ensuing year, Jim realizes running a farm is a lot harder than he expected, and decides to turn his farmhouse into the "Holiday Inn," which would be open only on holidays... about 15 days a year. And he writes songs specifically for each holiday. When he returns to the city to see his old friends Ted and Lila, he meets an aspiring singer/dancer named Linda Mason (Marjorie Reynolds), who was sent to sit at Ted and Lila's table at the club where they're performing by Ted's agent, Danny Reed... who had also told her about Holiday Inn, and that Jim was holding auditions. However, when she first meets Jim at the club, she has no idea who he is.
Later, she shows up at the inn to audition, and Jim sings her the song he'd written for Christmas, "White Christmas" (which of course became very famous in the real world, after this movie, and even inspired another movie of the same name as the song, which also starred Bing Crosby). Anyway, she gets the job, and the two of them soon become close. And... I guess other people work at the inn, but the only ones we get to know are the cook, Mamie, and her two kids. The inn opens for the first time on New Year's Eve, when Ted learns that Lila has left him for another man. So he goes to the inn after getting drunk, and dances with Linda. The next day, he doesn't remember her, but Danny tells him about her, and Ted decides she has to be the one to replace Lila in his act. So he and Danny spend some time trying to find out who she is, while Jim, fearing Ted will steal Linda as he had done with Lila, tries to prevent them from discovering that she works there.
The next holiday is Lincoln's Birthday, so Ted and Danny return to the inn that night, hoping to find the mystery woman. Jim convinces Linda that they should wear blackface in their act, not revealing that he just wanted to ensure his rival wouldn't recognize her. (The musical number they do on that holiday is one of the most excruciating things I've ever had to watch. I'm sure they didn't intend it to be racist at all, but holy crap was it racist.) Ted and Danny show up again a couple days later, for Valentine's Day, at which time Ted does meet and dance with Linda (sober, this time). That scene was kind of painful to watch, in a different way, because of the irony of the song Jim was singing while Ted and Linda were dancing. The next holiday is Washington's Birthday, and that... was pretty hilarious, for a reason I won't spoil.
Well, another major turning point in the plot comes on Independence Day, and again on Christmas Eve. (And things get kind of meta, when Hollywood comes calling.) But I really don't want to spoil any of the major developments. I'll just say that for the most part, the movie is quite funny, and it has some good music and dancing. And... I guess the romantic complications were compelling enough, even if it was hard for me to consistently think of either guy really deserving Linda. Still, I liked the ending, and almost the whole movie was fun. (Just, seriously, if I ever watch this again, I will have to skip Lincoln's Birthday, because damn.)