My FBI file was for hacking into my school district's AS/400 that handled my school's attendance and grading system. Somehow using a public IP address with no access restrictions allowed a clear telnet path in from home. Compounding username and passwords that were all the same for every employee. I didn't change a thing, just LOLed and told someone. Bad mistake. This was the late 90s. Oh well, 2 week suspension and…
At my university in the early 90s I went the white hat route and had tons of fun. I managed to convince the computing center folks to give me a student job in the Unix group, and then spent the next three years hacking their systems and getting a pat on the back when I did it.