My first 1/6 was the SDCC "Sith" Anakin. I had actually just quit my job and was in employed but my girlfriend at the time got it for me and it like many it started my high end collecting that has sprawled into Hot Toys and other prop replicas.
My cousin had that one when we were growing up. And I remember some kid had brought in their Kenner Han and Luke 12" to school and I was insanely jealous. But I was heavily into the 3 3/4" figures at the time (late 70s-early 80s). When Hasbro started making the 12" figures in the 90s-00s I was interested but never really liked how they looked. I thought they all looked way too "puffy" in their outfits. But I did end up getting a Jango 12" that had a sculpted body and removable helmet that I found on super clearance in KB Toys.
Finally in early 2008 I saw a web ad for Sideshow's Indy and discovered their website! It took me a while of debating but my wife ended up ordering it for me as a future birthday present since it wouldn't get released til the end of that year. Then of course I saw all their SW offerings and went ahead and ordered Smuggler Han which was due out that summer. So SS's Smuggler Han is the first high-end 1/6 SW figure and I haven't stopped since!