Jack Daniel’s Sinatra Select, Reviewed Just In Time For The Holidays

There are a fair few bottles of Jack Daniel’s on the shelf these days. Master Distiller Chris Fletcher and Assistant Distiller Lexie Phillips are taking the iconic brand to new heights by engaging with the brand’s heritage while also diving deep into their vast warehouses to find new gems. Today, we’re covering one of Jack Daniel’s most beloved expressions and a holiday favorite, Jack Daniel’s Sinatra Select.

I’m on the record as being a long-time Jack Daniel’s fan and advocate for all things Tennessee whiskey. Their Bottled-in-Bond is something that I actually pour and mix with day-to-day. Their Sinatra Select is a bit more of a special occasion bottle for me. I hadn’t tried for a fair bit (it’s been a year or so) until cracking a bottle open for this review.

Upon re-trying the special release this week, I knew I had to write a full review, especially with the holidays upon us. This is special whiskey that deserves all the accolades and love it gets. It’d also make a killer gift bottle if you’re stuck for a last-minute gift. Let’s get into it.

Jack Daniel’s Sinatra Select

Jack Daniel

ABV: 45%

Average Price: $172 (1-liter bottle)

The Whiskey:

Frank Sinatra was one of Jack’s biggest fans. So much so that the crooner was buried with a bottle. The actual juice in this expression is a throwback to how Jack was made in Sinatra’s day. They use special “Sinatra Barrels” that have concentric grooves carved into the newly charred oak, giving the whiskey more surface area to do its thing. Once that’s aged, it’s blended with traditional Old No. 7 and proofed at 45 percent, as it also would have been back in Sinatra’s heydays.

Tasting Notes:

Peach cobbler, apple pie with a buttery crust and caramel drizzle, vanilla pods, old leather, and a hint of cherry tobacco inside an old wooden box build on the nose. The sip leans into the fruit next to woody spice and soft leather that mellows dramatically towards a soft vanilla cream along with a very distant echo of cherry tobacco chewiness. The mild spice (think nutmeg) arrives late and is tied to a cherry syrup vibe that just touches on dry wicker, faint almonds, and a touch more of that tobacco. Ultimately, the leather returns and builds towards a silken finish with just the right balance of woody apple, cherry tobacco, and oaky spice — all touched by the softest note of vanilla bean.

The Bottle:

This bottle is grand. There’s a heavy bottom with about an inch of extra glass. The stopper is bespoke with a fedora carved into the plastic over the cork. It’s also big. You feel like you’re getting more than the average bottle (and you are).

The whole thing comes in a very hefty box that helps it feel like the perfect gift box. Inside, you’ll find a little booklet that describes the whiskey and the whole vibe of Sinatra-era of Jack Daniel’s and Tennessee whiskey.

Bottom Line:

This is one of the best of the best of the Jack Daniel’s line. It’s incredibly easy to drink while delivering an incredible flavor profile. It’s a great sipper that only needs a rock or drop of water to help the deeper flavors and textures bloom in the glass.

The Ranking:

98/100 — This is a tremendous whiskey experience and very close to perfection.