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Jack Daniel’s Sinatra Select vs Gentleman Jack: Which Wins?

Discover the differences between Jack Daniel’s Sinatra Select vs Gentleman Jack in this in-depth comparison and decide which Whiskey is better for You!

Jack Daniel’s Sinatra Select

NoseCharred oak, vanilla, baking spice
PalateCharred oak, banana, cinnamon
FinishMedium, cinnamon, vanilla, charred oak
Alcohol content90 proof (45% ABV)
How to drinkRocks
Similar toJack Daniel’s Single Barrel

Jack Daniel’s was Frank Sinatra’s favorite whiskey and this bottle tries to recreate the Jack Daniel’s of the good old days when it was bottled at 90 proof; it was later watered-down at 80 proof to extend availability.

Another important distinction is the use of charred American oak barrels with concentric grooves scored from top to bottom that expose the liquor to a greater surface area of both charred and virgin wood.

The nose hits with charred oak at first, followed by banana, vanilla, and a touch of baking spice.

On the palate, the Sinatra Select displays good body providing a pleasant mouthfeel. Flavor brings more oak char, followed by cinnamon, vanilla and a touch of caramel.

The finish is medium at best, with very little heat with more oak char which is constant from nose to finish, along vanilla and cinnamon.

I can understand why Blue Eyes liked this whiskey as it’s quite enjoyable, too much in common with the Old No. 7 just that better in every way as it feels robust, while missing the glue notes of the regular Jack Daniel’s.

Is it worth the lofty price tag? Yes if you are fond of listening to “My Way” if not go for the Woodford Reserve Double Oaked which has notes in common but way more affordable.

Gentleman Jack

NoseBanana, caramel, vanilla
PalateCorn, vanilla, caramel, oak char
FinishCorn, nutmeg, caramel, oak
Alcohol content80 proof (40% ABV)
How to drinkRocks
Similar toJD Single Barrel, Crown Royal

Gentleman Jack is the product of double-filtering the Jack Daniel’s No. 7 through handcrafted charcoal in a process that takes from 3 to 5 days before going through another round.

This double-filtering removes some of the weird and peppery notes of the traditional Jack Daniel’s making it easier to sip.

The nose brings the same plastic banana note present in every Jack Daniel’s release, along a hint of caramel and a touch of vanilla and a whiff of oak.

On the palate, Gentleman Jack feels thin lacking in texture. Flavor is high in corn up-front, followed by vanilla and caramel. There is some bitterness coming from an oak char note, but nothing too terrible.

The finish is short-lived, with more corn to it, a touch of nutmeg, caramel and oak.

If you have tried the classic Jack Daniel’s you are going to find the Gentleman Jack to be a refined and polished version.

Gentleman Jack is smooth, not too complex, but plain and watery. An improvement over the No. 7 which is not a major accomplishment as the latter is not that good, to be honest.

Overall, the Gentleman Jack is drinkable on the rocks but does not make a memorable whiskey; there are several good sippers at this price point that you should take in consideration before the GJ.

Sinatra Select vs Gentleman Jack: Price comparison

Prices are approximate and stated in USD:

Jack Daniel’s Sinatra Select$115
Gentleman Jack$26

Jack Daniel’s Sinatra Select vs Gentleman Jack: Which is better?

Sinatra Select tastes better

WhiskeySinatra SelectGentleman Jack
  • The Sinatra Select is quite nice and enjoyable making a good option for Frank Sinatra’s enthusiasts.
  • If you are not fond of Blue Eyes and his music then there are similar whiskeys like the Woodford Reserve Double Oaked that you should consider and save some good money.
  • The Gentleman Jack is a bit better than the regular Jack but it feels weak, watered-down and overy dull making me consider other alternatives at this price.

If you want to consider further options within this brand read my post: Discover the Best Jack Daniel’s Whiskey where I rank every release from worst to best!