Jack Daniels Gentleman Jack 750ml Gen 1 First Edition 1988 Boxed Whiskey RARE US

Offered here is an exceptionally rare and highly sought-after Generation 1 First Edition Jack Daniels Gentleman Jack, originally released in 1988, complete with its original black and gold presentation display box.
This is the very first commercial release of Gentleman Jack, predating later redesigns and label updates. Early examples in this condition — with original box intact — are becoming increasingly difficult to source worldwide.
Gentleman Jack was revolutionary for Jack Daniel’s, being charcoal mellowed twice — once before aging and once again after aging — resulting in an exceptionally smooth and refined Tennessee whiskey. This early bottling represents the original vision and profile before later production changes.
⸻
•Brand: Jack Daniel’s
•Expression: Gentleman Jack Rare Tennessee Whiskey
•Generation: Gen 1 / First Edition
•Initial Release Year: 1988
•Bottle Size: 750ml
•ABV: 40% (80 Proof)
•Country: USA
•Distillery: Jack Daniel Distillery, Lynchburg, Tennessee
•Packaging: Original presentation display box included
This is not just Gentleman Jack —
this is where Gentleman Jack began.
A cornerstone bottle for Jack Daniel’s collectors, American whiskey historians, or premium display collections.