Portland’s a great whiskey town: It fits the weather and my general mood (even improves it sometimes). 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. I do not personally believe that Sinatra Select is the best Jack has to offer but it’s also not the worst either.

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. Let’s get this out of the way – Jack Daniel’s Sinatra Select costs so much because of the special packaging and the name recognition of Frank Sinatra. Jack Daniel’s pays tribute to Ol’ Blue Eyes through their Sinatra Select Bold Smooth Classic Tennessee Whiskey. Special grooved “Sinatra barrels” allow the liquid to make contact with both charred and uncharred wood for a deeper and more complex flavor.Sinatra Select does not mention which floor the barrels were aged on, but I’m guessing it wasn’t the top. Even with 9 year old stuff like Coy Hill or the 10 and 12 year old versions, the oak is so non-descript it never speaks to its full maturity. The finish is better than the palate by a hair, leaving you with a positive feeling about what you just drank. What I mean by that is nobody that drinks Jack on a regular basis is going to be persuaded or dissuaded by what I have to say about Sinatra Select. Featuring a higher proof and longer aging process than JD’s flagship whiskey, Sinatra Select is one of the finest bottles in the brand’s portfolio, whether sipped neat or “Sinatra-style,” with three ice cubes and a splash of water.

Today, due in part to the Sinatra connection, Jack Daniel’s is the best-selling American whiskey in the world. As I would expect, a lot of the trademark Jack notes can still be detected like vanilla, caramel, honey and toasted wood.It’s achieved by first creating the barrel, then charring it, then removing the top metal hoops and head. The spice on the palate was slightly too much (strange of me to say for a 90 proof whiskey) but I’m reducing its score because of that. One of the more interesting tidbits was how they asked the TTB if they could modify the barrel like this. I added a couple of drops of water to it, which smoothed things a touch but also took away any nascent richness.