I'm 24. My parents bought a computer in 1994 but I wasn't really allowed to do anything with it except look at it and type my school reports on it. With those restrictions in place I never did use it much. All that changed when my family finally got Internet access in ~1997. A year later I rounded up all the money I had from birthdays, Christmas, etc up 'til then. I went and bought one of the first sub-$1000 computers. It was a P166MMx with 32MB of EDO-RAM and a 2GB hard drive. (I still find it impressive that 10 years later I have faster hardware in the palm of my hand for less than half the price.)

Anyways, I got fed up with Windows less than 6 months after buying the computer. Windows 95 had constant issues with conflicts between my ISA-PNP soundcard and ISA-PNP modem that I just *couldn't* resolve. I didn't have a CD-RW drive so I ended up buying a RedHat 5.1 CD from someplace for like $2. It took me about a month of dual booting to get my modem working. It took me, maybe another month to get my sound card working. I remember the constant crashiness of Netscape 4.05 and the horrible Windows 95 look-n-feel that the RedHat 5.1 desktop aspired to. I remember the horror that was Gnome 0.54 and the pain of Redhat dependency hell (which I circumvented by compiling everything from source ). I ended up trying Debian, playing around with it for a couple weeks then going back to RedHat because I was used to it. I got so fed up with the RedHat dependency situation that I think I switched back to Debian inside a day and comfort-level be damned. In all the operating systems I've ever used since then (Linux, Unix, *BSD, Windows and Mac) I have never found a package management tool I liked better than apt on Debian/Ubuntu.
Also, fun thread. Good to see a nice off-topic thread that hasn't ended up in flames or rants.