The first Gentleman Jack generation

On this page I will show you the other whiskey that the Jack Daniel's distillery is making besides the regular Black and Green label. The Gentleman Jack whiskey. A Jack Daniel's whiskey mellowed twice. It got a very smooth tast and is a bit "softer" than the Black Label Jack Daniel's. Gentleman Jack's smooth character is a result of Mr. Jack's dedication to the old-time charcoal-mellowing method. Gentleman Jack is charcoal-mellowed twice - once before it's aged in those charred white oak barrels, and once again four years later before it's bottled.

The first generation Gentleman Jack was only sold in the US in 1988 till 1989 and available in three sizes:

  • 50 ml
  • 375 ml
  • 750 ml

The first Gentleman Jack folder + introduction 1988

This letter was mailed to members of the Tennessee Squire Association back in 1988. Along with the letter came this newspaper artical and a black and white picture of the first bottle. Click on images for a (printable) close up.

Click on images for a (printable) close up.

50 ml size miniature Gentleman Jack

This is the first generation miniature bottle. It had a plastic cap. The one on the left has a label that is all the way around the bottle. Both of the labels got the barcodes. The bottle on the left is very rare and as far as I could find out it's from the first run of these miniatures!

The tin is a pretty rare item and has a estimate value of over $ 150.00 easy... I have put another second bottle inside of the tin to show you the difference between the 1st and the 2nd generation.

The original 50ml bottles were shipped in small cardboard boxes containing 12 bottles, not the pretty little boxes used today, within the larger master carton. the box was pretty bland, with just some wording and a printed GJ horse and rider logo. The carton was very similar to the standard cardboard boxes used today for the larger 375, 750, 1L, and 1.75 bottles.

One cool item from the first Generation of the Gentleman Jack miniature bottles is this cardboard box with two bottles. The label goes all around the bottle!

The tin is sold only with 1st generation bottles.

Gentleman Jack 375 ml 1st Generation

On the pictures below you will see the 1st, the hybrid (the "in between" generation) and the 2nd generation 375 ml bottles


(On the picture from left to right; 1st Generation, the Hynrid and 2nd Generation)

Gentleman Jack 750 ml 1st Generation

On the pictures below you will see the 1st, the hybrid (the "in between" generation) and the 2nd generation 750 ml bottles


(On the picture from left to right; 1st Generation, the Hynrid and 2nd Generation)

The first 750 ml size bottle was sold in a nice cardboard box and wrapped in paper like this one:

750 ml

Gentleman Jack 1st Generation cap

Top cap of the 1st Gen.

The Gentleman Jack Taste Test bottle

This is a very rare 750 ml Gentleman Jack taste testing Bottle. Not for sale off course in liqour stores.
White colored whiskey before Charcoal mellowing. The only thing that's surpriced me was the Tax seal...??? There should not be a tax seal on this kind of bottles because it isn't for sale purposes...??? The cap is sealed.... Strange...

We are talking about a very rare bottle dated 1988.

Gentleman Jack 1st Gen. Package deals

The package deal below is one of the first I bought. I still got the bottle and the book but trow away the box...

Click for close up >
(This bottle and box are a part of the D. Alexander collection © )

Gentleman Jack Extra item

This a Gentleman Jack sniffer glass.

The 750 ml size bottle was sold in the US with this great leather bag. The bottle has a screw top instead of the "old cork" like on the first generation bottles.


(this bottle and leather bag are a part of the D. Alexander collection © )