Heads, Hearts and

Whiskey Tales

Sharing stories of good whiskey, good friends, and good memories

I don’t know Jack,

and That’s Okay

July 2020

We were on the plane towards Eastern Europe when my friend Jay says he’s going to get some Jack Daniel’s to put him to sleep. “Put you to sleep,” I say, “that would just make me air sick!” He protested and said, “Jack is awesome.” I’ve tried to bring him into the ways of good whiskey before but he just won’t have it. He’s too A.D.D to take more than 5 seconds to pay attention and taste what he’s drinking. He just gets his Jack Daniel’s and makes fun of me for spending time and money on good booze.

After a long boring flight, we ended up on a layover in Finland and found the airport bar. It was a whiskey bar called The Oak Barrel. It had a full sized mock-up of a copper pot still inside and was appointed with a decent selection of single malts. Jay got a beer, I got a Lagavulin. I was conversing with the bartenders about the whiskeys. One bartender was a local and the other was an ex-pat from the U.S.  In the midst of the conversation the American bartender makes reference to “The best whiskey in the world” and holds up a bottle of Jack Daniel’s. I thought he was joking but he was quite serious. Jay elbowed me and said, “See that, must be pretty good stuff”.

After the flight into Estonia, we found the hotel and decide to go out into the old part of Tallin for some food and drink. Wandering down century old alleyways, we found a bar called Nimeta Baar, or No Name Bar. It had three large front windows that were hand painted. Two of the windows were painted with the name of the bar. The other was painted with a Jack Daniel’s bottle label. Jay nodded towards the window as we walked in and said, “See that, must be pretty good stuff”.

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As we were sipping our drinks and taking it all in, I glanced around and then looked up. Above the bar was a line of empty bottles of Jack Daniel’s. They circled around the top of the bar and the rest of the room on a small shelf near the ceiling like a freight train stalled on the tracks.


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As I was staring, almost straight up at this, mouth half open, I came to my senses and snapped my head down to level. Too late, Jay saw me and looked up to see what I was looking at. Seeing all the empty bottles displayed like trophy heads he elbowed me and said once again with a gleeful grin, “See that, must be pretty good stuff.” He was delighted that so many in this land agreed with him on his high opinion of Jack Daniel’s. 

I looked at him frustrated, “You know what?” I said, “I’m going to drink some Jack Daniel’s. I’ve been talking down about it but I haven’t drank it in years, and everybody on this side of the earth seems to think it’s some kind of imported nectar of the gods. So, before I leave this country I’m going to taste some Jack Daniel’s. And I mean really give it a fair tasting like I would any high-priced bottle.” “Really?” Jay says excitedly. “You want to do some shots right now?” “Hell no!”, I retort, “I’m going to have to get myself mentally prepared for that.” But if I can’t find any redeeming attributes in Jack Daniel’s after that, you have to agree to try drinking better whiskey.  

A week went by and it seemed as if every bar or restaurant we passed or went into had a sign advertising that they served the esteemed Jack Daniel’s Whiskey. It really was considered top shelf over there, and my swill-drinking colleague would not let me live it down.

So finally, an evening alone provided the opportunity. I ascended to the Horisont Bar at the top floor of the Swiss Hotel in Tallinn. It was pretty dead, but it was still early. There were a few customers here and there and the bartender was mixing a drink. I bellied up to the bar and asked for a glass of Jack Daniel’s neat in a snifter, a double. At first the type of glass was lost in translation; the bartender presented a small double-glass. I repeated “Snifter” and pantomimed the shape of the glass with my hands. He reached up and found the right vessel and reflected the smile on my face when I saw it and nodded.

I could tell he was intrigued that I was planning to taste something special. But when I repeated my request for Jack Daniels, a double, he kind of crinkled one eye, raised an eyebrow and tilted his head as if to say, “All right, I guess, if that’s what you want?”  He measured a pour into the glass and repeated the procedure. He slid over the specimen as I dug for a pen and a piece of hotel note paper that I had brought for the occasion.

I gave the glass a good deep smell. Nose prickle! Didn’t expect that from an 80-proof whiskey but then it was my first sip of the night. Okay, so maybe I just need a few sniffs to settle into this one. I take another sniff, still hot. No problem, I’ll bring it down with some water, like I would with a cask strength. I add a little water and take another sniff. I can tell a few of the other guests in the bar are trying to figure out what I’m doing.

The bartender asked in broken English “Trying to guess what is in it?” I try to explain that I’m giving Jack Daniel’s a fair test. He was not as optimistic as I would have expected based on the enthusiasm towards this whiskey by the rest of his countrymen. But then he has a little better whiskey selection to draw from at his back than most other bars around here. The shelf behind him had the Johnnies, Black through Blue, Royal Salute, The Livets, Fiddich, some Glenmorangies, Talisker, Laphroaig, The Macallans 12, 18, 21, 25… and Jack Daniel’s.

Despite my selection he had figured out that I’m really into whiskey as I raised the glass to observe the dark color and thick, strong legs easing down the inside of the snifter. I finally took the first sip. Sweet… then burn. At first it was smooth in the throat as a peppery burn sets into my palate. Slowly the burn descended down into my throat and then it was hot from lips to gullet. I retired from the barstool to move to a cocktail table off to the side of the room.

I continued to sip. After a while I got past the alcohol and could start to taste vanilla and some honey. There was a slight desirable bitter taste in there. The bar was filling up with people dressed to the nines. This was a classy, cool place overlooking the Baltic Sea from hundreds of feet above the street. 

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I finished my glass. I was struggling to enjoy this spirit but decide to stay strong in my commitment to give it a fair tasting. I ordered a second Jack Daniel’s double in a snifter. I took a sniff…ouch, nose prickle again! Okay, now I know it’s not me, this is a strong alcohol smelling whiskey.

I was adding some water for my next sip when the bartender loomed in with a shadow and presented a new snifter of whiskey onto my table. I looked up puzzled and he said, “Tell me what is this,” and walked away. He was challenging me! Okay, I thought, be cool, I can do this. I took a sniff and got a smooth smell of malt. I knew it was a scotch, and a nice one. My immediate association was Glenmorangie but a sip or two later the maltiness got more pronounced. I then began to think maybe Macallan. I decided not to try to guess the distillery but first rather try to narrow down the region and approximate the age.

It smelled and tasted like a Speyside to me, and a nice one. It was viscous and malty and pleasant to sip, but then after a glass of Jack Daniel’s that wasn’t too hard to achieve. At first I was thinking a 12-year old Speyside. I start to look at the choices behind the bar and my mind started to wonder what he would give me. I no longer thought it was Glenmorangie, maybe Macallan, (not a Speyside but a Speyside at heart, as they say). It didn’t have those chocolate notes I get from the 12-Year and it’s definitely not the 21 Select Oak.

I took another sip and was really enjoying it. I knew it couldn’t be the Mac-25 as it didn’t have that deep sherry-oakiness, and also because I knew he wasn’t giving away free shots of that. I was beginning to think maybe the Macallan 18-Year Fine Oak. I reached back in my memories. I used to always have a bottle of it on my shelf at home but haven’t for a while. I searched back, I took a sip and closed my eyes, I imagined that I was back at home in my whiskey study sipping Macallan-18 Fine Oak. I wasn’t confident but decided to commit. 

The bartender walked over to my cocktail table. I was still unsure, but I proclaimed - Definitely a single malt scotch, 18 years old, The Macallan. He said with his accent “You got type of whiskey right and year right but wrong distillery. Is Glenlivet-18”.

Failure! But I think I still impressed him if only by his watching my calibrated process, wrong as it was. I coughed up that the Jack Daniel’s had numbed my taste. I really think it did. But that was just an excuse.


I sipped the rest of my Glenlivet and enjoy it and smiled at the fun I had with the challenge. I looked at the deep snifter of Jack Daniel’s still sitting there on my table staring back at me, waiting, and I made a face. I can’t do it, I thought. I tried, I really did, I gave it a good try but I just don’t like Jack Daniel’s.

I walked over and set the full snifter of Jack on the bar and announced, “I can’t drink this shit.” 

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The bartender laughed and said, “That is called up-selling.” I furrowed my brow and told him to give me a Macallan-18. I introduced myself. His name was Henno. I could tell he really felt good about himself as he dumped the Jack down the drain and poured me a glass of the expensive stuff.

A sniff, a sip, I was in my memories again. I took my glass across the room into the cigar lounge as Henno followed. He suggested an aged Montecristo, Open Regata. He lit my cigar with perfect protocol and returned to the bar. I was in the cigar lounge alone for the moment. It was dark and dramatic with black leather and ebony hardwood. The aroma of my cigar was perfect, suede and coffee. A lady entered the room for a cigarette and the aroma of her perfume blended with the moment.

My cigar was burning into the apex of flavor when Henno returned, eager to hear my critic of his suggested smoke. We talked a little, he was busy, but I could tell he would have loved to sit and talk about whiskey and cigars. He was a pro and it showed. I could tell that even before he poured my first drink, when I first walked in and saw him mixing that cocktail. I always judge a bartender by the way they handle the mixer, Henno had the over the shoulder technique down. And to watch him present, cut, light, and re-present my cigar was a delight. Henno returned to the fray of the filling barroom as a few others enter though the smoke into the cigar lounge. I enjoyed the scene with the smell of tobacco, leather, and sweet perfume. Sounds of foreign tongue and smooth jazz. The ladies were dressed to kill.

I finished my Macallan which I truly enjoyed and decided to pair the rest of my cigar with a Balvenie Doublewood. Henno brought it and it did not disappoint. 

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After the Montecristo I returned to the bar. The room was now filled to capacity except for my empty table. As I walked over I noticed a small plastic sign on the table that read “Reserved”. Henno caught my eye from across the room and gave me a nod and I knew he put that sign there for me.

I finished my Balvenie and progressed on to a Talisker-18 for last-call. I scaned through the window out across the cold, dark Baltic sea and the view coupled with the flavors of my smoky sip - I scanned across the room and the view of classy ladies paired with the sweetness in my glass. I was taking in the atmosphere and contemplating how I had started this evening and my quest to disprove my friend’s opinion of his favorite libation. 

Tomorrow night I’ll be drinking with Jay again and he’ll certainly ask me how my experiment with Jack Daniel’s went. I thought about my ridiculous quest to make him like the whiskies that I like. I reflected on how the flavors in my glass are only a small portion of the enjoyment of drinking it. That the smells and sounds around me, and sights and interactions with others is what truly make the moment. Tomorrow night I’ll order my whiskey and then I will buy him a double shot of Jack Daniel’s. Although I may not appreciate the flavors of his favorite spirit, I do appreciate the fun we have hanging out drinking whiskey together. And when he holds up his glass and says, “See, this is good stuff!” I’ll look around the room, take it all in and reply, Yes Jay, this is good stuff. 

Cheers, TW