My early ventures into Tennessee whiskey were in my youth, where the goal was simply to get drunk, and involved foul tasting cheap stuff. There was one unfortunate episode with a bottle of Cutty Sark that was rapidly passed back and forth between 3 of us until it was empty. And of course in those days there was lots of beer. Lots and lots of beer.
Then, in my early 30's, I stopped drinking completely for about 20 years. By then, I had tapered off to having a beer occasionally, and there just wasn't enough money in the budget for beer anymore.
The journey into better taste actually began in my mid 40's with custom roasted coffee, and the realization of how much better that was than the mass market coffee I typically consumed. That lead to trying micro brewed beer and imported ales, to see if the flavor was an improvement over the mass marketed stuff. To me, the difference was profound.
The beer search ultimately lead to trying good whisky just a few months ago. After trying a decent bourbon (Woodford Reserve), I decided to give a bottle of Macallan 12 a go, and was instantly hooked on Scotch. I've only tried about 10 so far, each with its own unique flavors. I'm 56 now, and have discovered a simple pleasure later in life. Sitting back with a glass of Scotch is a (somewhat) affordable luxury that I enjoy immensely.