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.
TLDR; It started as a young teen who just wanted to get games for free; It continues because companies don't give two flying hoots about me.
Currently, I pirate because I can't rightfully give any money to these anti-consumer companies that will only victimize me. I can't own anything anymore, and this absolutely frustrates me. If I could own the media I purchase, I wouldn't pirate anymore. (by this I mean I wouldn't pirate the media I consume. I'd still data hoard because it's a literal addiction, please help!!)
I don't pirate games anymore; or better said, I rarely pirate games, and when I do they're ran in a VM with VFIO because I really don't like the idea of running arbitrary code on my system; even though we have reputable, vetted, and trustworthy groups. (As a general rule, I don't trust what I can't verify.) I buy all my games on Steam for convenience, and I opt to use Goldberg's Steam Emulator (which is open source!!) to store backups of my games, and this setup works wonderfully! I stay away from games with invasive DRM like Denuvo (I play these in a VM), and I've long stopped buying EA and Ubisoft games. The only forms of media I pirate nowadays are movies, and music (and the occasional game).