In terms of software I've pirated mostly older stuff. Like, I pirated the Legacy of Goku 2 because I wanted to play it again for some reason and finding a retail copy was difficult. Old NES games, SNES games, etc.
In general though, if a game is reasonably available, I'll purchase it legit. I even purchased games like Mario RPG which I already had on an emulator. I just enjoy it more on an actual system for some reason.
But I've pirated a ton of music. I think I've paid for one CD since Napster made it so easy. I also pirate wrestling events. I used to be a big WWF/E fan. Nowadays not so much, but I still pirate the odd event to check it out.
For me it comes down to how much I care about the thing. I like video games, and I want to support the industry, so I rarely pirate something that I could find legitimately. With music, I don't care as much, so I pirate it.