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.
I found a website that showed my how to use RSS feeds to automatically download TV shows. Having my favorite shows download automatically overnight was very convenient. There was no streaming services for TV shows back then and even if there was, my internet was way too slow for that. I had a portable media player with a massive 80GB hard drive that I could load my pirated TV shows and ripped DVDs on when I was away from home.