Remember when JPGs took multiple seconds to download? When your digital camera served up horrid pixel slop? When you actually scanned things? That was mental millennia ago, but there are probably traces sitting on your hard drive. What's the oldest?
Now it's possible that you're a ruthless eraser, importing the minimum from your old system when you upgrade to a new computer. But you might also be a somewhat sentimental hoarder, keeping copies of everything for posterity (or nostalgia). If so, crack open those folders and tell us what you can find.
As for myself, I'm afraid the above crushingly nerdy picture of Super Monkey Ball toys I bought in 2004 is as ancient as it gets. Ugh.
Share a link to your oldest photo in the comments and the Aussie editors will import the best back into this article. So let's see what you've got -- especially if it's more embarrassing than mine!