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RobertMG

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That's rather easy to do. To have seen it in the last ~30 years or so you pretty much had to have:

Had parents who were a fan and made a point to tape it off late-night airings and/or purchased the DVD
or
Been born before ~1960. After ~1970 it pretty much got relegated to late-night airings (along with many other pre 70s Christmas films).

Once White Christmas came out, and was pushed hard in the 60s, Holiday Inn pretty much fell by the wayside. White Christmas has most of the songs from Holiday Inn (it was intended as a partial remake of the earlier film) and enough of a plot change to make it feel familiar yet still be new. I still remember the first time I saw White Christmas. I kept wondering where certain songs, that I knew were in the film, were. The farmhouse set is almost identical to that in Holiday Inn and many of the trappings are identical/similar enough that I truly thought I was watching Holiday Inn almost until the end of the film. I first saw White Christmas on a BW TV so there was no color to tip me off. So... if you've seen White Christmas you'll have several deja' vu moments when watching Holiday Inn.

One warning.

If you're PC sensitive there's a particular song section dealing with Abraham's Birthday (once a stand alone Holiday, now combined with Washington's and others to make "President's Day") with Crosby in blackface that now comes across as a bit racist. That same song has a section with the maid and her kids singing a particular line with a now verboten word once used to describe blacks (no, not the "N" word), but the term used was not at all uncommon during the slave years, which the song somewhat depicts. I do find that little bit with the maid and her kids somewhat charming (the kids are terribly cute) and am not bothered by the word (it's an archaic term and was when I was growing up, but it's appeared in hundreds of books and films). I've heard complaints about the way the maid talks. I think those are unfounded. I grew up in the South and knew lots of black folks who spoke in just that manner. It's dialect - something every race has, good and bad. The song is rather catchy, but I've never liked the blackface bit (I've never liked any of them and always wondered why they just didn't get black folks for such parts).

PC stuff aside, this is one of my absolute favorite Christmas/Holiday films.
Here in NYC White Christmas was a staple on WABC's The 4:30 movie and it was broken up over 3 days. Then the film vanished, our impression was Irving Berlin or Bing did not want it out ay longer until Paramount released the videotape in the 1980's along with Christmas stockings! Holiday Inn got a huge boost one Sat night when NYC's channel 5 showed it on their old MOVIE CLUB show one early Dec night they even showed It's A Wonderful Life too!
 

RobertMG

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A product of its time yes. In addition, I am sure that Bing Crosby would never have intended a slight of African-Americans. To people of his generation and Al Jolson's, black face was just a style and indeed one that paid a compliment to black entertainers.

I don't particularly like the Abraham number.
Just check out Bings camaraderie with Louie Armstrong in High Society. Sadly as many have said it was a product of it's time and needs to be seen to show how far as a country we have come. Think about such talents as Nat King Cole having a TV show yet going to perform live and needing to stay in different hotels.
 

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