Michael Hack wrote:... there are those that might just grab the EW off the shelf thinking its JD

There's a woman, the wife of a familiar contributor to this forum, who's husband once did exactly that, quickly and furtively buying two bottles of what he mistook for old 90-proof JD at a tiny backwoods liquor store, only to find his error upon unbagging them at home. Unfortunately, the woman's name is Linda (the "L" part of "L and J dot com").

Michael Hack wrote: Wouldnt EW be better off developing a sleeker, cooler bottle
As Chuck pointed out, EW (and Ezra Brooks, Virgin, Kentucky Rain, & probably Beam Black as well) were knockoffs of the very successful JD image. But your point is a good one: the whiskey has long outlived the need for user-confusion and could certainly stand on its own; why continue the copy-cat packaging?
Well, why'd you try it? There are other whiskeys out there that DON'T look like they might be half-price substitutes for JD, but you chose EW. So did I, long before I became a bourbon enthusiast. And like you, I made EW my normal whiskey mainly 'cause I liked it better (Beam white label and JD being the only other brands I knew then), with the price being frosting on the cake. But that label, with the paid-for-by-BrownForman advertising to support it, was a big factor in my trying it in the first place.
Actually, Heaven Hill is doing what you suggest already. It's just that it's their premium bottling of EW, the 9 to 10 year old "vintage dated" single barrel, that they're focusing their attention on. To good effect, too, as EWSB packs a pretty good marketing wallop on its own. Maybe it's better for us if they leave EW7black alone (and cheap)
