Funny / Railroad Tycoon

• In "Island of Hope" in Tycoon 2's Second Century campaign, as in other maps the identities of train robbers is reflective of the map and the storyline. In this case, your trains will be robbed by "starving mob", since in the story food is very scarce. This leads to the Black Comedy of papers triumphantly declaring "Starving Mob Captured!" and celebrating it means no more train robberies.
• The game over message in the "Hell and High Water" mission, where the map is flooding. "So, how long can you tread water?"
• Certain maps in Tycoon 2 do not allow any track to be built that is not connected to the rest of a company's network. On a map like China, this can lead to the Epic Fail of an AI player starting their company in a place like Taiwan, which does have two viable cities on the map but which is separated from the mainland by a sizable stretch of open ocean.^note In the expansion Gold and Platinum Editions, you can build a bridge spanning ocean tiles to get to or from an island; the AI generally never does this, probably owing to the Shockingly Expensive Bill, or the inability to process water tiles as being valid for rail placement.
• The randomly-generated naming system for depots and secondary stations around a city can lead to some amusing instances of Department of Redundancy Department, like from the Western USA scenario in the original game, potentially things like "Grand Junction Junction" or "La Crosse Crossing". There can also be the visual irony of a place like "Rapid City" being only a square or two of village that is not going to grow at any such pace.