Trail of Robin Hood (1950)
Actually, I'll field that last one now: you shouldn't. While this is sort of interesting as a cultural artifact, it doesn't hold up 71 years after its creation. In fact, I'd call it a stretch to refer to this as a movie at all. Which brings us back to who Rogers was and why his "movies" are somewhat distinct.
I doubt anyone will be shocked to learn that Roy Rogers was a stage name, but if (like me) you've never subjected yourself to any of his movies, you might not realize Rogers is also the main character in the majority of them. You could look at this as an actor playing a fictionalized version of himself, but I honestly don't think that captures the spirit. I think it's more accurate to say an actor named Leonard Slye was playing Roy Rogers both on- and off-screen to give the impression that the fictional pioneer Roy Rogers was starring in movies about himself.
All of this was tongue-in-cheek, of course - these movies were intended for kids. And that also means they were made fast and cheap. Trail of Robin Hood was one of six movies Rogers was credited in from 1950 alone. Coupled with the fact this had a runtime of just over an hour, it looked and felt much more like an episode of a television show than most movies I've seen from that era.
Keep in mind, that's an observation, not a complaint. This was made just before televisions become common in American homes, so kids wanting a regular fix of their genre of choice had to rely on the big screen. This was filling a niche - nothing wrong with that.
Now that we've gotten all that out of the way, let's talk about the utterly bizarre western, Trail of Robin Hood. First of all, it's important to note the term "western" is being used in the traditional sense, in that it's set in the west. I don't think I'm alone in forgetting that the genre isn't technically defined by the era, but rather by tropes associated with that era. This seems to simultaneously take place in (for lack of a better term) an "Old West" pioneer town and the year 1950.
The story centers around two competing Christmas tree farmers. One, a big city tycoon, is trying to drive up profits, while the other is an aging movie star playing himself who wants to sell his trees at or below cost to ensure everyone can afford one. The movie star's name, of course, is Jack Holt.
Weren't expecting that, were you?
Roy Rogers plays a conservation agent named Roy Rogers trying to keep the peace when the rival tree farmer's lackey starts committing felonies to win. These quickly escalate to murder, kidnapping, and arson, the latter of which leaves Holt in bad shape. A young girl calls all his old friends from his acting days to enlist their help, which they happily do by [checking notes] threatening to crush a man to death to compel him to provide information. The movie ends with the western movie stars driving Holt's trees across a burning bridge before it collapses, and with Rogers battling a villain until he inevitably falls off a cliff.
Actually, it's kind of a running theme for the bad guys to either get themselves killed or to murder each other. Anything to keep the hero from having to get his hands dirty. At any rate, the tycoon winds up partnering with Holt, because God forbid this was seen as anti-capitalist or something.
It occurs to me that in speeding through the synopsis, I may have inadvertently made this thing sound fun. Please understand this wasn't my intent: even at its short runtime, this dragged.
I assume the presence of a dozen or so big-name western stars playing themselves was thrilling to fans in 1950. Not to take anything away from the concept - it's objectively a fun meta plot point in a series that's already somewhat meta around its lead, but the decades render the point moot. I got the idea from context, but I had a best a vague recollection of the names being uttered as cameo after cameo showed up.
Also, it's somewhat difficult to square the alternate dimensions at play here. If Roy Rogers is a character, how can he interact with real-life actors? We're pretending Rogers is his character, but the others aren't (at least not completely - they're all presented as real-life heroes and expert marksmen). I know this was all meant as a joke, and it probably worked well enough when it was made. But that's of course academic to someone watching this today.
What ages a little better is the humor around the character Sis, a young girl who's played for laughs despite being comically good at virtually everything she sets out to accomplish. I'm not saying this makes the movie worth watching, but the gag works better than I'd have expected.
Likewise, some of the stunts are well executed, particularly when fire is involved. There's nothing exceptional, but I feel like I need to acknowledge there are moments the production values improve.
The title seems to reference Holt's philosophy, though that would have worked better if his rival hadn't switched sides at the end. It is interesting to note that it's Holt's character, rather than Rogers, who seems to be the thematic core of the movie (though Rogers gets virtually all the action scenes). Holt is also the moral center of the story - overall, this feels like a tribute to the aging actor. I suppose they timed it well - he passed away just a year later.
This definitely isn't something I'd recommend unless you're an especially forgiving fan of westerns from this era. That said, I can't bring myself to rate it too harshly, either. This wasn't made to compete with movies from that era that endured. This is an episodic story built around a sort of meta-character and intended for fans. And in that context, Roy Rogers succeeded well enough to produce a massive number of these things (and go on to star in his own TV show a few years later).