Awesome / Railroad Tycoon

• Any time you can simultaneously buy out a rival player's company AND leave them so deeply in debt that they cannot recover.
• Successfully completing some of the hardest campaign scenarios — India in "Croissants or Crumpets" and Africa in "Cape to Cairo" from Railroad Tycoon 2 come to mind — especially on higher levels of difficulty.
  • The narration of the ending cinematic after completing "Cape to Cairo" is particularly grand, with the narrator recounting that you began by pounding in spikes in Baltimore, and by this time you've wrapped the entire world up in a "big iron bow".
• Or in general, building and successfully running a rail network that spans an entire continent.