Inspired by a post since deleted, I feel bad for probably coming off judgemental about the poster's taste in the movie that drove him to consider sailing.
The earliest desired media I can remember that drove me to figure out sailing was DC Talk, a Christian rock band. Pop music was not allowed in my house, so a Christian group was tantalizing and scandalous to a rebellious, young Vanth. Things escalated from there.
My dad got into Kazaa in the mid-00s, then Limewire, before discovering Mininova and TPB. Just kinda saw what he was doing and thought it was interesting. (We were often told not to touch the computer as it'd "knock off his download"...)
I seem to recall one of the first things I pirated was... er, Pirates of the Caribbean, which I watched with my friends huddled round my laptop. Quality times.