Tuesday, September 08, 2026

Trailer Tuesday: Santa Fe Trail (1940)

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Directed by: Micheal Curtiz.
Written by: Robert Buckner.
Starring: Errol Flynn, Olivia de Havilland, Raymond Massey, Ronald Reagan, and Alan Hale.
Cinematographer: The Great Sol Polito.
Composer: The Great Max Steiner.




I love old Warner Brothers movies, and love the work of director Curtiz and his discovery Errol Flynn and his frequent co-star de Havilland (8 films together!) but had somehow never seen this movie until one night years ago when I caught it on late night TV with my dad. I think it might have fallen into public domain, which is why it was off radar. But why? Look at that cast! This film was compared to GONE WITH THE WIND (in Warners advertising) when it was released! It's a big epic western adventure story about a bunch of historical characters who would soon become famous... before anyone knew their names. And a huge event in history.

But SANTA FE TRAIL’s fall into obscurity was not so strange as the film goes on. The story starts with Flynn playing Confederate hero J.E.B. Stewart, and Ronald Reagan (?) playing George Armstrong Custer, and a pretty good cast of Warners guys playing other members of a graduating class at West Point - all of whom would become famous Civil War guys... but the film takes place *before* the Civil War when all of these guys are friends. It starts as kind of the military version of a college comedy with all of these guys joking around, once they graduate into the army, it’s kind of a buddy comedy with Flynn and Reagan... and DeHaviland as the gal they both love. But this buddy comedy gets oddly side-tracked when the plot is introduced...

The story is about John Brown, played amazingly by Raymond Massey, who is a strange figure in American history. He was anti-slavery... to the extreme. A religious zealot who believed slavery was un-Christian. That The Lord made us all equal. Before the Civil War, he waged his own war - coming to the western territory of Kansas after receiving mail from one of his numerous sons that Kansas may become a slave state. Brown and his army raided farms and freed slaves... and killed the slave owners. In cold blood. Often rounding them up and executing them. Then arming the freed slaves and making them part of his army. So we have a guy doing terrible things for a good cause. Not easy for a popcorn audience to see him as an evil villain - because his reason for doing all of these terrible things is on the right side of history, and he's a very religious guy. This should have been one of those great Warner Brothers dramas like DR. ERLICH'S MAGIC BULLET (about syphillis!) or BLACK LEIGION (about the KKK in our time), but it ended up a big glossy Flynn/DeHavilland adventure comedy. Say what?




So joking Flynn and Reagan are the Army guys sent to stop John Brown from freeing slaves in Kansas.

Which makes our heroes kind of fighting *for* slavery.

And J.E.B.Stewart (Flynn) would later become a Confederate hero... along with some of the other joking supporting characters in the film. Flynn even has a little speech about how the South doesn’t appreciate the North butting into their business, and if given enough time and they will eventually taper off on the use of slaves. I wondered how much of this stuff was to placate the southern film audience and how much was trying to show how complicated the issue was at the time. Either way, the result is a movie that is not black and white (even though that’s the film stock used). Our heroes are guys trying to stop a guy from freeing slaves. I’m sure that’s why Warners "accidentally" let this film fall into public domain obscurity.... but the more I think about the film, the more I think about it... and how many breezy buddy comedy westerns provoke this much thought? The Stewart speech is all about the right way to do things and the wrong way - and using the violence of war to create social change. And the guy they are hunting, John Brown, is doing just that - he is a mini Civil War. It’s easy to disagree with his methods but agree with his goal. Nothing is simple in this film... There is no “right” side.

And that's an issue in a breezy comedy adventure film. But also one of the things that might make it interesting to a modern audience. It's a film that doesn't work because the issues at the core of the story are too complex for entertainment... but maybe that provokes a discussion about those issues? Trying to blend the peanut butter of Raymond Massey's great performance and interesting character with the chocolate of the Errol Flynn romantic adventure story just doesn't work as entertainment... but (dispite probably a million historical errors because this *is* a Hollywood movie, not a history lesson) maybe it works as education? Maybe people will watch this and look up the real characters and go down the rabbit hole of pre-Civil War history and John Brown?

Dead Reckoning There are lots of good battle scenes, and some goofy stuff with Alan Hale as comic relief, and the romantic triangle, and some great suspense stuff with Flynn behind enemy lines and some drama with Brown’s wounded son captured, and all of the scenes you’d expect in a lightweight buddy comedy western... except the Brown story and Massey’s great performance (he makes you believe in his cause, and that killing slave owners in cold blood might be necessary) are way out of place. Too serious for the Reagan-Flynn banter scenes. It's an interesting example of how chocolate and peanut butter might be great in a Reeces candy, but sometimes things just don't mix well. The subject matter is way too serious for a fun Errol Flynn movie. Something to think about in your screenplays and stories - does the tone of the story undercut the story itself? If the two are at odds, you are going to end up with a film that just doesn't work... and might end up falling off the edge of copyright into public domain and show up on late night TV for insomniac screenwriters to watch.

The film leads up to the siege at Harper’s Ferry Armory, which is the big action set piece at the end. It stays pretty close to the facts (except the real Armory isn’t some boxy Hollywood sound stage set and on film the siege lasts a couple of hours instead of, I think, four days) - to the point of having Flynn’s character *not* be the guy in charge of the forces. The battle could be part of the buddy comedy film... but after that we go back to the serious Raymond Massey film about John Brown - as he’s captured and sentenced to hang and gives a passionate speech before the quick drop and short stop.

You could say this film has the most confused politics of any film ever made - but maybe that was the point? Maybe the idea was to show just how complicated the events leading to the Civil War really were. The result is a film that seems like oil and water when you watch it... but you end up wrestling with the issues long after you’ve watched it.

So maybe worth a watch on the late late show if you find yourself unable to sleep. Despite the confiused politics, it's a good example of bantering buddy comedy adventures... but I prefer Curtiz and Flynn and DeHavilland in CAPTAIN BLOOD.


- Bill

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