I've fond memories of jailbreaking (TIFF exploit at jailbreakme.com) moments after the exploit was published on IRC. Used Installer to install apps because Apple said they would never allow third-party native apps and that WebClips were the way of the future.
The same bug was also used to jailbreak the PSP and other random devices. For a few years I would occasionally get mail from people thanking me for helping them jailbreak their DVD player or smart appliance.
I've never actually owned an iPhone, I wrote an exploit for Linux/x86, then someone else (cmw) ported it to iPhone and made the jailbreakme website!
That is delightful and brightened my day! Thanks for sharing :)
My memory may be hazy, but I don't believe the iPod Touch was ever released publicly with iPhone OS 1.0. Arrived at my front door a few days before release in store and was running iPhone OS 1.1. Had encryption enabled where as iPhone OS 1.0 shipped to the iPhone 2G (that's cellular 2G) without it enabled for some reason. Whatever the reason that was a big help to the early jailbreaking community.