Wright Thompson, senior writer for ESPN, was asked if he remembered the first time he'd tasted it: "I do," he said. "It didn't taste thin and gasoline-y – I don't have the official words. But it felt like if I poured it over a spoon, it would coat the spoon."
Thompson thought the lore of the elusive Pappy, like the sports heroes he usually writes about, was worth a book: "Pappyland: A Story of Family, Fine Bourbon, and the Things That Last" (Penguin).
"You get the sense that the bourbon is almost an accidental by-product of these people just living their lives," Thompson said. "And maybe that's why people go so crazy for it."
The current keeper of the Van Winkle secret is Julian Van Winkle III. "I think you think you know yourself pretty well, 'til someone else starts writing about you," he laughed.
His son, Preston, has spent nearly a lifetime as his dad's able apprentice: "I was younger than the whisky I was selling when I started working for my dad," he said.
At the distillery there are barrels that won't see the light of day again for two decades or more. Bourbon is almost generational in that sense.
Julian started young, fixing leaky barrels for his dad, who had learned the craft from his dad, Pappy himself.
Pappy is so storied, he has his own exhibit at the Frazier History Museum in Louisville. "He was a great old guy," said Julian. "He was very dapper with his little vest on and smoking his cigars. He was a very unique individual, a real salesman."
Pappy used wheat instead of rye in his bourbon recipe, which gave it a smoother, sweeter taste.
His vow is still bolted to the distillery he co-founded on Derby Day in 1935: "We make fine bourbon, at a profit if we can, at a loss if we must, but always fine bourbon."
"It's what my father and grandfather were always doing, was selling aged bourbon whiskey – really good aged bourbon whiskey," Julian said.
But by the 1960s, even the finest bourbons had gone out of favor. They were dinosaurs with a cork.
"It was like an 'old man's drink' – you know, 'My grandfather used to drink bourbon, but we sure don't drink that stuff anymore.' It's one of those kind of a deals," Julian said.
Wright Thompson said, "Yeah, I mean, if the last time you had bourbon was Kentucky Tavern in college, like, you know, the difference between this and that is like a hood ornament and a racehorse!"
What today is as rare as an ice cube in the Sahara was, back then, gathering dust – and Julian's dad was forced to sell the family distillery in 1972.
Cowan asked, "Do you think he ever got over selling the distillery?"
"No, I don't think so," Julian replied. "No, that pretty much did him in, I think, in the end. It was just, it was his life. I mean, he brought it home every night, so it was a tough deal."
He died of prostate cancer just a few years later.
Cowan asked, "Did you feel a pressure to carry on the business? Or was it a desire, really?"
"It was the only thing I knew how to do to earn a living, basically," Julian replied.
So, he started over – from scratch, really. With a beat-up truck and a forlorn distillery he bought in 1981, he set about honoring something old, even though the beverage world had moved onto something new.
"Did you ever think about giving up?" Cowan asked.
"Nope," Julian replied.
Julian's daughters – Carrie, Chenault and Louise – confirmed that.
"We didn't realize what was happening all that time," said Chenault.
"And he didn't either, honestly," added Carrie. "He just knew how to work hard."
"He was always fixing stuff, and rolling barrels," said Louise. "He would come home with a bleeding head or a sprained ankle."
No one paid Pappy much mind, until 1997, when the Beverage Testing Institute in Chicago got its hands on some Pappy. It gave it a 99 out of 100 – the highest rating ever given to a whiskey.
The suggested retail price for a bottle hovers around a few hundred bucks, but you'll never find it for that. On the secondary market a single bottle usually goes for thousands.
It's so rare that it's a news event when the few bottles of Pappy are released. "I feel like I got the 'Golden Ticket'!" said one smiling customer in Alabama.
Some stores have even resorted to using a lottery to decide who gets to buy even one bottle. Customer Nate Hill said of the Pappy Van Winkle bottles, "People call them unicorns. Supposedly they're out there, but most people don't see 'em!"
Cowan asked, "Did you always intend to make less you could sell?"
"Not a good, smart move!" Julian said. "It would be nice to have more. And we're making more. But the demand keeps going up. So, I don't think we'll ever get there."
No one knows when bourbon goes into a barrel if it will make the trip – if angels will drink more than their fair share, as it evaporates over the decades. "Every now and again you'll see the word 'empty' [on a barrel], and that's just a gut punch," said Preston.
But what is left isn't just a family's loved-and-cared-for whiskey. What Wright Thompson discovered in writing his new book was that the real spirit in a bottle of Pappy isn't its rarity, or its price, or frankly even its taste. A bottle of Pappy is all about those who have gone before us.
"When you get it now, what you get is a son and a grandson's memories at work," Thompson said. "I find that really powerful and moving."
Cowan asked, "For you, this really isn't a book about bourbon at all, is it?"
"It's barely a book about bourbon," he said. "It's a lot about what we owe our families, and how we can pass the best of them along."