In my high school days, if I could I would have pirated N64 games. I spent so much money on N64 games ($59.99, with tax it was ironically $64.64).
Don't get me wrong though, N64 housed some of the best games I've ever played and enjoyed. Goldeneye (before the hype), Super Mario 64, Perfect Dark, WWF No Mercy/Wrestlemania, Legend of Zelda OoT / Majora's Mask, Rogue Squadron, etc. I also had a Playstation and a couple of years later I bought an add-on to let me play burnt games.
But now I'm in college and actually have money to spend on video games. But in reality, if I was able to buy games in high school, everyone else should be able to (by getting a job!). You're paying for entertainment. 60 hours of entertainment out of a video game (ala Fall Out / Elder Scrolls) justifies a purchase. I bought some crap games too full price in the past (i'm looking at you SNES!)
In the end, I mainly buy the games worth purchasing (team fortress 2). The problem is that China has mass produced ways for playing pirated games for the DS. When I get my new iphone, I don't plan on jailbreaking it as I want to fully support the devs on that platform. Some devs don't even recuperate the development costs when their games become pirated