Jack Of Owls
Arcane
For me it was MicroProse's Conflict in Vietnam for the C64 oh so many years ago. I had been successfully completing with ease fairly adult and difficult games like Pool of Radiance and Dragon Wars previously, along with simulations like Red Storm Rising and Project Stealth Fighter, so I felt I was obviously a genius and no game was too difficult. "Bring on your best, hardcore computer sim world! I'm READY!" was my war cry. Then I played Conflict in Vietnam. I was brought to my knees like the lowly occidental dog I actually was. What about you? What was your first humbling experience in gaming when you realized your brain was half the size you originally thought?