By chance I stumbled across the adventures of ARROWHEAD in the pages of Atlas's early 1950s comic THE BLACK RIDER. I've only read two of them and don't have an overview as yet. The format was that Arrowhead was a renegade perpetually on the run from the law like the familiar Kid Colt, and just as perpetually got mixed up in other people's troubles. Both stories I saw were signed by Joe Sinnott.
In some ways the post-apocalyptic world of Gold Key's MIGHTY SAMSON is pretty typical. However, one has to appreciate that when Samson and his buddies encounter a series of monsters controlled by Oggar-- who's the "Mister Hyde" to a human "Doctor Jekyll"-- each monster gets a well-defined cognomen.
In ADVENTURE COMICS #155 (1950), long before it was routine for heroes to "meet and instantly fight," The Shining Knight got to contend with the Greek hero Bellerophon, whose flying horse Pegasus was the model for the Knight's own mount. It's a nice little yarn, apart from the distinction of Frank Frazetta's evocative pencil work.
One of the lesser aspects of Howard Hughes' notorious 1943 THE OUTLAW is its status as a crossover, spinning a fictional story about the encounter of two western legends, Billy the Kid and Doc Holiday. In real history the two men were contemporaries but there's no record that they ever met, much less quarreled over a horse and a woman (in that same order of importance.) A fictional version of Sheriff Pat Garrett appears in the movie as well, but I consider him ancillary to the legend of William Bonney.
In keeping with my idea that time-travelers meeting with "legendary" historical figures *may* count as icon-crossovers, one possible source of same is the long running JUMBO COMICS backup feature STUART TAYLOR. I've never paid it much attention because it's very dull. But the title-less story I call "Ghost of Sleepy Hollow" from JUMBO #35 departs from the usual routine of time-traveler Stuart Taylor showing up in historical periods to mess with people from the past. In "Ghost," Taylor believes for some reason that the purely fictional characters of Irving's "Legend of Sleepy Hollow" are historically real, so he and his girlfriend travel to the past to meet Ichabod Crane and Brom Bones. Taylor champions Ichabod by exposing Brom's pose as the Headless Horseman. The girlfriend does nothing but sneer at Ichabod for being a wimp.
The 2003 LOONEY TUNES BACK IN ACTION flick, reviewed here, includes a sojourn to Area 52, where the government stores such alien monsters as the Robot Monster, a Trifid (maybe), the Man from Planet X, the Metalunan Mutant and a couple of Daleks. Not seen in the shot below is another captive, The Fiend Without a Face.
The Legion of Monsters concept, given a one-shot appearance in 1976, got upgraded to a limited series in 2011. Review here.
