Well my beginnings are fairly recent still, so I've got a good recollection if them.
I was having cheap blends quite regularly (albeit on the rocks), not thinking it was worth my money to buy "premium", and one birthday my wife gave me a bottle of Glenmorangie 10.
In hindsight, she probably regrets ever doing so, and she sure wishes I hadn't found this site.
A short time thereafter her father bought me my first Dalwhinnie 15, and that just sealed the deal for me. I gave up the ice and started buying different malts in that pice range, and I'm now looking at taking another step up as I learn to appreciate them more.