Whiskey Advent Calendar Tasting: Gentleman Jack
This is part of my series on tasting notes from the 2021 Drinks By The Dram Bourbon Advent Calendar.
Whiskey for December 5th, 2021: Gentleman Jack
The distillery
You probably already know who Jack Daniel's is. They make Old No. 7, aka Black Label, aka "What you get when you order Jack Daniel's". They invented the Lincoln County Process, which filters distillate through charred sugar maple wood. You've almost certainly had a Jack and Coke at some point in your life, or at least heard of it.
Jack Daniel's has been around since 1866. They closed up shop for a bit in 1919 due to The Badness and reopened again in 1938, well after prohibition ended due to state level laws. They closed again in 1942 to 1946 due to World War 2. In 1956 they sold to Brown-Forman Corporation, a giant spirit and wine conglomerate.
They've branched out in recent years with their Single Barrel Select offering and a number of liqueurs built off a Jack Daniel's base. Old No. 7 / Jack Daniels Black Label is the best-selling whiskey in the world, selling 12.5 million cases in 2017.
In 2020 they got a new Master Distiller, Chris Fletcher, and we'll see if he shakes things up in the coming decades.
The whiskey

Introduced by Jack Daniel's in 1988, it is double filtered, which Jack Daniel's calls "double mellowed". Jack Daniel's offers their own video tasting guide for Gentleman Jack if you're interested. The quick breakdown is:
Nose: Sweet with Vanilla and Caramel.
Taste: Sweet and mellow with no oak. Tingly and warm.
I find it interesting that the taste has very little info about what it tastes like and video ends by saying it should be very palatable to a lot of people. I've had Gentleman Jack a number of times before, but I'll try to enter this like it was something new.
Look
Light coloring with red and gold tones. It swirls thinly and makes a few weak legs from the glycerine. Not too surprising on a filtered product. Gentleman Jack is clear and bright in the light.
Nose
Surprisingly fruity. I expected more caramel and brown sugar, but it's much more citrusy than expected. It's sweet to smell but not overly so. I actually don't get much vanilla either. Maybe when it opens up with water.
Taste
The body is thin, as expected, but sweet and surprisingly spicy. Reminiscent of a high rye bourbon. There's a lot of black pepper spice, but also leather and tobacco. It's not particularly complex or layered, but has a nice hit and a short finish with just the memory of the rye and alcohol burn hanging out in your mouth.
After water
A little water brings out the sweet sugar smells and mutes the citrus to leave a little cherry hanging out there. The water leave the taste mostly the same, with a big spicy punch that fizzles out. It might even leave just a hint of smoke hanging out in your mouth.
Summary
This isn't what I remember getting in the past, I recall gentleman jack as one dimensional and sweet, and I'm happy to be proven wrong with this sample. It's not something I'd go out of my way to track down, but it's sturdy and if you're in the mood for a whiskey that's a big spicy splash without a lot going on, you could do a lot worse.
It's interesting to see that it's come down in price to under 30 for a 750ml, so as far as everyday whiskeys go, this fits a niche you don't see very often from the budget boys.