Yeah, I remember watching "Freedom Downtime" as a teenager and thinking how ludicrous it was that he was sentenced to prison for computer hacking, but now that I think about it as an adult of course he should have been. Sure solitary confinment, the specifics of his sentence, etc. may have been extreme and I'd like to think that the court system has progressed in their knowledge of computer security since then, but what he did was still a breach of corporate security. He knew at the time it was illegal, and he just thought he was too smart to get caught.
That idea that we had at the time that it was a "victimless crime" or something was very immature.