Back when I first discovered torrent downloading, I downloaded pretty much everything. Any song or movie I wanted was on my 750 GB external hard drive, which I was pretty proud of back then. I had an N64 emulator too. I used to work at the front desk in the dorms in college...though really all I did was play Harvest Moon 64. Good times...

Now that I can afford to buy games, music, and movies I'm interested in, I don't pirate nearly as much as I used to. Probably the only thing I download illegally are rare songs or anime episodes that aren't on Crunchyroll. I'm a one service man.

I only ever pirated movies and songs. And even that was way back in the late 90's. Napster then KaZZa if anyone remembers those.

Only a couple Zelda games on emulators (A Link to the Past and Four Swords Adventures). The reason for that was because I wanted to play catch up on the series. I've been wanting to make up for that by buying the VC version of the former. Would be cool if there is a Wii U version of Four Swords Adventures as well.

I definitely remember Napster when it was the first incarnation. Downloaded matrix.avi.mp3 successfully off it :)

Of course, I'm playing right now Mother 3 on a friend's phone. Not exactly pirated, but still playing an unofficial and illegal version.

Aside from games though, I of course have seen many pirate movies, but I still have never bought one. 

Eddie Murphy's Delirious and Raw were my very first downloads. Good times.

Pirating? Pffft.... I've obviously never tried that! /s

Demo's. That's pretty much it.
Minecraft, Fallout New Vegas, and a few others from pirating sites. It was less about playing than it was about trying them out. Once I realized how much I liked both, I bought both.