whiskey comparison

Jack Daniel's Sinatra Select vs Gentleman Jack

Jack Daniel’s Sinatra Select and Gentleman Jack evoke thoughts of maturity, class, and smoothness, well at least the brand names do. Ever since I reviewed these two Tennessee Whiskey, albeit quite far apart, I’ve always wondered how similar they might be and if Sinatra Select could remotely justify being 4+ times more expensive than Gentleman Jack. If you’ve been wondering as well, then wait no more.


To the best of my knowledge, the main differences between the whiskeys, besides proof, are that Sinatra Select is aged in special grooved barrels for extra oak contact while Gentleman Jack is charcoal filtered a second time (the standard Old No. 7 is filtered only once). I wouldn’t be surprised if there were age differences, but Jack Daniel’s does not provide any detail. Still, at face value none of these seems like compelling reasons for the price difference. Maybe there’s some other special sauce in there to justify the price, so let’s find out in this Jack Daniel’s Sinatra Select vs Gentleman Jack whiskey comparison.


The below table outlines key facts and figures for each whiskey.

Sinatra select vs Gentleman Jack comparison table SITE

How do they Compare?

Sinatra select vs Gentleman Jack radar
Sinatra select vs Gentleman Jack traits table SITE

And the winner is...

Sinatra select vs Gentleman Jack winner compressed

Sinatra Select is so much better than Gentleman Jack. That’s not necessarily saying much though because Gentleman Jack is mediocre, inoffensive, and boring. Getting into the scents and flavors, Sinatra Select has many of the same caramel, banana, vanilla, and nut traits as Gentleman Jack, but with a lot more low-end darkness and overall richness to every trait. The difference is so great that after sipping Sinatra Select first, Gentleman Jack loses all its flavor and tastes like new make spirit. Sinatra Select is a fuller and rounder Gentleman Jack, but it’s still a decent whiskey at best.


Now that I know that Sinatra Select is the superior whiskey, I still don’t understand how it costs so much more than Gentleman Jack. Yes, there’s branding, marketing, and those special barrels, but solely from smell and taste, Sinatra Select isn’t anything special, probably good for $40. I initially thought that Gentleman Jack would be a decent substitute for Sinatra Select, but I no longer believe that. Old Forester 86 Proof Bourbon may be more appropriate, but more to come on that.  

Maker's Mark Cask Strength Comparison