Portland’s a great whiskey town: It fits the weather and my general mood (even improves it sometimes). On the positive side of things, I do legitimately think that Sinatra Select stands out enough from other, more standard Jack Daniel’s offerings by how it tastes. This exposes the whiskey to extra layers of oak which imparts a rich amber color, bold character and a pleasant smokiness, followed by an incredibly smooth vanilla finish. But if you are an enthusiast who has lots of experience with various whiskies, this is one you can confidently skip.

What’s interesting is I am picking up on this “ashy” scent that I am sure comes from the residual wood that was carved out when the inside was grooved. It’s bold and flavorful, yet mellow enough to sip neat, and italso shines in classic cocktails like Old Fashioneds or Manhattans.

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One of the more interesting tidbits was how they asked the TTB if they could modify the barrel like this. What I immediately find to be interesting is that rather than it just smelling like banana bread the whole time, I find some lively, fruity aromas like citrus peel and a little bit of cherry. Does that mean that the power of a singer/crooner who died 25 years ago and whose last album came out 40 years ago really holds this much power? These factors make a huge difference in the final product, which is far superior to the current watered-down and unbalanced flagship Jack Daniel’s.It doesn’t come cheap, but Jack Daniel’s Sinatra Select Tennessee Whiskey is a fitting tribute to the star: bold, smooth, and excellent in its field. Jack Daniel’s pays tribute to Ol’ Blue Eyes through their Sinatra Select Bold Smooth Classic Tennessee Whiskey. The grooved barrels in which it’s aged put the liquid in contact with both charred and uncharred wood, giving it a richness and complexity lacking in standard Jack Daniel’s. We combined our widely praised Neat Glass with one of our 3oz Flight Bottles and housed them together in a custom EVA travel case.

I mean, of course you’re reading this review and have probably guessed it’s Sinatra Select and you’d be correct. It’s hard to imagine now, but when Frank Sinatra was allegedly first introduced to Jack Daniel’s by comedian Jackie Gleason at New York lounge Toots Shor’s, the company was small and relatively obscure—not quite the equivalent of today’s “craft” brands, but you get the idea.

It even manages to hold its own when served Sinatra-style, with three ice cubes (no more, no less) and a splash of water.

As usual, I sampled this neat in a glencairn but I don’t think Frank Sinatra would have ever drank it that way. Whether you think it’s worth the ring-a-ding-ding depends on how big a fan you are of Frank and/or Jack. According to Tales of the Cocktail, in 1955, Sinatra announced onstage, “Ladies and gentlemen, this is Jack Daniel’s, and it’s the nectar of the gods.The smooth, bold character of the whiskey embodies the smooth, bold character of the man himself, Frank Sinatra.