Rocks or neat?
Rocks. Fewer, larger cubes is the way to go. Or a single ice sphere. You’ll get the chilling effect without dilution.
Cocktails or straight?
That depends on the whiskey. If I’m drinking Gentleman Jack, I like a cocktail. If I’m drinking something more like a Single Barrel or a Sinatra blend, I’ll go straight. I do what the whiskey tells me.
So what’s a good whiskey for cocktails?
In the Jack Daniel’s range, I call Gentleman Jack our “cocktail whiskey,” because it’s gone through mellowing a second time. Your classic whiskey cocktails contain some form of bitters, so if your whiskey has a lot of oak, it’ll compete with that (because they hit the same tastebuds on your tongue). Gentleman Jack lets you keep the bitters light, but keep them prevalent. All of the worst whiskey cocktails I’ve had have the same thing in common: people had overdone the bitters in them.
What’s the best whiskey cocktail you’ve ever had?
I was in Berlin years ago for the bartender’s convention, and someone made me a single barrel old fashioned, and they kept it real simple. It was a brown sugar cube, an orange peel, they zested the glass a bit, and they bruised the orange peel and the brown sugar cube together. And then they just dropped single barrel and ice on top of it. I had to go up and shake the guy’s hand.