The Dream of the Fisherman’s Wife: the same guy who did The Wave also painted this in 1814.

The Flying Train (1902): this is amazing footage and such an inspiring view of alternative modes of transportation from the past. {via}

[UPDATE: Someone colorized and 60fps’d the footage and it adds in some missing realism.]

Landing on the Melbourne Citadel in Microsoft Flight Simulator: the backstory on this is someone mistakenly entered “212” into OpenStreetMap instead of “2” for the number of stories that a building in Melbourne, Australia had. Apparently, the information in OSM is used to generate maps and landmarks in Microsoft Flight Simulator, which just released a new version, and the monstrosity in this video was the result.

[UPDATE (8/21/2020): And the Washington Monument looks less accurate. Found an article with more examples.]