Time for a silly old movie about time travel! A Connecticut Yankee in King Arthur’s Court (1949) is based on a Mark Twain story, which already had two earlier film versions and would go on to be adapted and interpreted many more times. In this one, Bing Crosby stars as 1910s American mechanic Hank Martin who gets bumped on the head and wakes up in 600s England. He’s taken to court by Sir Sagramore (William Bendix), where Hank falls in love (at first sight, mutually) with King Arthur’s niece Alisande la Carteloise (Rhonda Fleming).
This is far more of a rom-com than a swashbuckler and features four songs (three by Crosby, one by Fleming). Their relationship moves the flimsy plot along, fluttering like her gossamer sleeves and fluffy red hair. There’s a framing story where Hank visits Pendragon Castle and annoys the tour guide by inserting his personal recollections, like how he knows this lady in the painting:

So Hank is taken to see Lord Pendragon (Cedric Hardwicke) where he shows the pendant that matches the one in the painting and tells the story in flashback.

At the court of King Arthur (also played by Cedric Hardwicke), Alisande sings and dances wearing this pink satin fantasy medieval princess dress that 10-year-old me would have killed for. Mary Kay Dodson is credited as the costume designer, but Edith Head is listed and uncredited, so no idea who came up with this one.

Later, when Hank and “Sandy” (as he calls her) get romantic, she wears this flowy blue-ish gown. While her outfits skew very fantasy, Hank’s one costume has a slightly more medieval maybe 13th/14th-century vibe. The gold-on-red print is excellent, along with the hanging sleeves. I scoff at his almost a pork-pie hat — yeah, it’s actually related to historical shapes but I know they’re trying to let him look like “Bing Crosby.”
Fleming’s costume has survived, but it’s faded quite a bit.

There’s also a gratuitous scene where Hank rescues Sandy, who’s chained up, hair flowing free, legs exposed.
The whole court is a mishmash of lurex and bedazzled medieval clichés.
Morgan Le Fay (Virginia Field) is supposed to be a villain, but she isn’t given enough scenes to really play that out. I like her red outfit though.
The framing story ends, and Lord Pendragon tells Hank to go chat with his niece — who coincidentally looks just like Alisande!

Have you seen A Connecticut Yankee in King Arthur’s Court?
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I’m not the only one getting stronger ‘Cute Couple’ vibes from the red-on-red Morgan/Our Hero photograph, am I?
Also, if I had to offer a suitably cartoonish explanation for that very non-Medieval portrait of a Dark Ages princess-type, I’d claim it was a fairly recent attempt to capture the likeness of a historic person using a distantly-related modern person who just coincidentally happens to be the spitting image of her Great Great Great Something Something (Not least because this would provide an excellent pretext for some “Of course she probably didn’t looking anything like that” “ACTUALLY…” jokes, as well as some foreshadowing for the reveal of Miss 1910).
If you’re going to do old movies, may I suggest 1939’s “The Old Maid”?
Okay, I was not familiar with this story, though the familiarity of the plot gives me a good chuckle. If you told me that “a 1910s American mechanic hits his head and wakes up in King Arthur’s era” was the plot for some modern day isekai-anime, I’d probably believe you. Heh, the more things change, the more they stay the same… Either way, that 1910s gown looks very lovely
I remember seeing it decades ago on Dialing for Dollars! I watched it because 1) der Bingle was in it, 2) there wasn’t much else to watch on a weekday afternoon. I remember I enjoyed the movie. and later I enjoyed the book by Twain even more. other than that, I haven’t seen this version in a VERY long time. I know Whoopie Goldberg did a version of it.