It's hard to figure out where your American whiskey is coming from. There are a handful of bottles I like, and strangely enough, they all happen to be "brands" managed by a company called Kentucky Bourbon Distillers[0] who only recently got into distilling their own stuff.
On the one hand, if you find a product you like, who cares about the story behind it?
On the other hand, when some brands are charging an arm and a leg (like Pappy Van Winkle) as other, less expensive, brands made by the same people with the same equipment (like Buffalo Trace), then it might be worth it see what the difference is between the "high end" and "lower end" brands.
I did a blind taste test and found I liked the mid range whiskey the best.
A related issue is that there are still stocks of aged whiskey from distilleries that have closed long ago - and they get sold to independent bottlers and existing distillers alike.
Side-by-side comparisons are often misleading in hedonic sensory evaluation. Even trained individuals have a tendency to select the sweeter and stronger flavored (intense) product.
Bitter and woody notes are important balances in higher quality bourbons, but are often perceived as negatives when doing comparative evaluation.
This is likely from your description, as the higher end bourbons tend to be wheated and lighter, but with a more prominent woody body from their longer barrel ageing.
Adding to JasonCEC's comment, a semi-famous example of this phenomenon appeared in the blind taste-test challenge Pepsi marketed vs Coke.
Pepsi, being slightly sweeter, was preferred when participants took a single small sip for a taste test. However, when drinking an entire can, people were more likely to prefer the less-sweet Coke.
I've never understood this one. To me Pepsi always tasted like a diet product. Sure it is sweeter, but never the right kind of sweet. And I can't comprehend the people who can't tell the difference between Pepsi and Coke.
I think the canned varieties of both taste pretty metallic, but especially Pepsi.
I've taken to opting for the glass-bottle varieties of both; whether it's the lack of aluminium traces in the soda, the use of sugar instead of high-fructose corn syrup, or me having opportunities to collect bottle caps as if I'm trying to make a living in a post-apocalyptic nuclear wasteland, I've found that to be much more enjoyable for whatever reason.
That all said, RC Cola is the superior beverage. ;)
On the one hand, if you find a product you like, who cares about the story behind it?
On the other hand, when some brands are charging an arm and a leg (like Pappy Van Winkle) as other, less expensive, brands made by the same people with the same equipment (like Buffalo Trace), then it might be worth it see what the difference is between the "high end" and "lower end" brands.
I did a blind taste test and found I liked the mid range whiskey the best.
0 - http://en.wikipedia.org/wiki/Kentucky_Bourbon_Distillers