I’m just old enough to remember finding Pappy Van Winkle on the liquor store shelfs. I can still remember the last bottle I found in the wild. I was in Effingham, right when the Van Winkle boom was kicking up, and there was a bottle of Pappy 12 for $80. I snagged it. I drank it, not realizing at the time what was about to happen to the whiskey industry.

The last time I drank Pappy 23 was the day I started my new job nearly three years ago. We were in Chicago for my training and we found a bar that had it. My boss bought me that pour, and it meant a lot to me. By then, the markup was steep. But, it was a special occasion.

So when I saw Wright Thompson, an incredible sportswriter, had a book on Pappy, I was thrilled. Finally, a book on an iconic bourbon.

But, I quickly learned Always Fine Bourbon would just be a side character in Thompson’s Pappyland. Early on, Wright let’s us know this book will be in first person, because it was as much about him as it was whiskey or Julian Van Winkle III.

Oh. Okay. But that isn’t what I signed up for.

Turns out, I should have trusted Wright Thompson. He turned this “whiskey book” into an introspective deep dive into heritage, legacy, relationships, what we inherit, what we leave behind, the moments in between that make us who we are and why that all matters. The moments that call for an Always Fine Bourbon. My wedding ring was made with whiskey barrel wood. If that doesn’t scream incorporating whiskey into special occasions, what does?

Wright weaves his story in with Julian’s. And yes, I fill comfortable using both first names after spending the past couple of weeks with them in my ear. It is that kind of personal. Wright’s burgeoning fatherhood, Julian’s chasing a memory (nostalgia is undefeated). It all mixes well, like a Vanhattan.

The history of Van Winkle whiskey is in there, from the famed Stitzel-Weller to the modern Bourbon Trace. But the heart of this book is in two men dealing with their pasts and wondering about what lies ahead for their families.

I went from skeptical, to crying in a Mach 1 parking lot at one point. I’m not going to say which part, because that is something for me. But, this book triggered some thought processes for me. The people in my life who helped shape me, the impact I would like to have on this world and the fear I’m likely falling short of that goal. The special moments I have had and the ones I’ll likely never have. And really, those are the best books. Books of whimsical fantasy are fun, books of personal development are useful, but the books that make you ponder your own life are the ones that resonate. Pappyland did that for me.

I don’t re-read too many books. This one will make the short list, circling back around every few years; not because I need to remember the story, but because I need to check in on my emotional state.