> I want to say that it was on the gumdrop shapes macs but I know the school got some of the first iMacs around that time as well.

The "gumdrop shaped macs" were the first iMacs and were released in 1998 (I remember this well because that was around the time I worked for a publishing company so had to deal with MacOS 8 and 9 a lot as well as wiring a gigabit Apple Talk network (at the time that was very futuristic).

I had similar tails of exploiting my school network. Though it was Windows 3 and I way playing Wolf3D loaded via a program called something like "Object Manager" that allowed you to embed data into winword (might have been related to OLE?). Those machines were null terminals so the game was installed into my user area. Unsurprisingly I got caught but thankfully deleted the executable just moments before hand so I only had to make an excuse for the WAD files.

At college I upped my game and write a RAT which I installed on every PC on the network. I actually managed to get away with that one, albeit there were a couple of near misses. One time I got caught because some mates sat next to me were playing games. When questioned what I was doing I confessed to the lesser crime of also playing games because writing malware would surely have seen me suspended (or worse) rather than having my IT privileges revoked for 24 hours! That college did eventually find the RAT on the network but only after I left, but assumed it was someone else. It wasn't until my brother got a job at the college IT department ~5 years later when they realised it was me who installed the software.