I started with c64 but stuck there with basic ( extension port was broken unfortunately could not dive into assembly there )
Then I got from someone an old 286, ( hdd was not working ) spent most of my time on "debug" command. Then I got a book for x86 assembly and DOS (interrupts etc). ( Which was kind of hard on non-english speaking country ) I still somehow recall some pages from memory :)
Dived into cracking/cheats, made even money on password recovery. How long those x86 knowledge carried me was unbelievable when I look back.