In June 2011, Wright Thompson, a writer for the now-defunct Grantland, cold-called liquor stores in three U.S. cities to see if he could score a same-day purchase of Pappy Van Winkle, the wildly popular Bourbon. He struck out and was laughed at for his chutzpah.

“There’s a cult,” says Thompson. By the time he’d embarked on his experiment, Pappy Van Winkle wasn’t just a spirit. It was a sensation, a single-monikered icon (“Pappy”). These days, it’s capable of raising $10,000 at charity auctions.

How did this happen, exactly? When did Pappy Van Winkle become “Pappy”?

Maybe Pappy Van Winkle became a household name when Anthony Bourdain first drank it in a 2012 episode of The Layover. He proclaimed, “If God made Bourbon, this is what he’d make.”

Chef Sean Brock may have stoked the flames when he touted the Bourbon at his acclaimed restaurant, Husk, in Charleston, South Carolina. Chef David Chang did likewise at his Momofuku spots in New York City.

The fact of the matter is, there wasn’t just one thing that turned Pappy Van Winkle into an impossible-to-find unicorn. As more people started to talk about it, Pappy became famous for being famous. You might not have known quite what it was, but you knew you needed to have it.

What is Pappy Van Winkle?

When we refer to “Pappy,” we are talking about anywhere from three to seven whiskeys. It depends on how lax your classification system is and how much you want the prestige of Pappy’s name.

There’s Pappy Van Winkle’s Family Reserve 15 Year, 20 Year and 23 Year. There’s also Old Rip Van Winkle 10 Year and Van Winkle Special Reserve, which some people call “Pappy 10” and “Pappy 12.” There’s also the Van Winkle Family Reserve Rye (“Pappy rye”) and a one-off called Old Rip Van Winkle 25 Year Old that debuted in 2017.

All range from good to great in quality, and from expensive to incredibly expensive in price.

Of course, it wasn’t always this way. There was a time when Pappy Van Winkle was just. . . Bourbon.

It’s a relatively new label, after all, not some century-old brand like Old Overholt or Old Grand-Dad. It’s not even Wild Turkey or Maker’s Mark, which have been around since 1940 and 1954, respectively.

Pappy Van Winkle whiskey debuted on liquor shelves in 1994, when the 20 Year was first released. The 23 Year came along in 1998, and the now standard-bearer 15 Year Old bottle launched in 2004.

During this time, bottles of Pappy Van Winkle were readily available at liquor stores for far less than $100. Today, of course, Bottle Blue Book, an online price guide, lists new bottles of the 15 Year for around $1,000.

The “Pappy” origin story begins well before 1994, though. It starts with a man who was, yes, named Pappy.

Who is Pappy Van Winkle?

Born to a family of lawyers and educators in Louisville in 1874, Julian Van Winkle was only 18 when he left Centre College to begin his career as a traveling liquor salesman for the Louisville-based W.L. Weller & Sons. The company sold whiskey and produced “cologne” spirits, which amounted to high-proof swill with added color and flavoring.

By all measure, he was great at his job. In 1915, when the company’s namesake patriarch, William Larue Weller, died, Van Winkle and another top salesman, Alex Farnsley, bought the operation. They had already begun to produce their own whiskey in conjunction with another company, A. Ph. Stitzel.

The Stitzels were sticklers about quality whiskey—no coloring, no flavoring, no rectifying—and that fit Van Winkle’s ethos just fine.

These Bourbons speak to iconoclasm in a distinctly American accent.

Eventually, Julian became president of Stitzel and, in 1933, the merged Stitzel-Weller company was formed. Luckily, they already had some well-aged Bourbon stock, as Stitzel had been one of only six U.S. distilleries allowed to produce “medicinal” whiskey during Prohibition.

Van Winkle’s first distillery opened on the day of the Kentucky Derby in 1935. It was unique in that it only produced a wheated Bourbon because, well, that’s what the Stitzel family had always made.

Legally, then and now, all Bourbon must be made from at least 51% corn, plus typically 5–10% malted barley. When the rest of the mash bill is occupied with wheat, it makes a sweeter, smoother and more accessible Bourbon.

For a long while, Stitzel-Weller was the only major Bourbon distillery that used wheat, which was a big hit in its Cabin Still, Weller and Old Fitzgerald whiskeys.

American Craft

To modern whiskey connoisseurs, Stitzel-Weller Bourbon is still some of the very best whiskey ever made.

“As far as Stitzel-Weller goes, it’s of course going to get a big boost from the Pappy halo effect,” says Kris Peterson, a spirits archivist who sells plenty of vintage Stitzel-Weller at his Chicago bar, Hush Money. A two-ounce pour from a 1960s Cabin Still decanter goes for $135, or you can pay $600 for two ounces of Very Old Fitzgerald 12 Year distilled in 1963.

Unlike some other historic brands, these whiskeys are consistently good. The flavor profile tends to be balanced, Peterson says, and the rich mouthfeel keeps the high proof in check.

“If someone is going to drop that kind of money to drink, they usually want to make sure it has the highest possible success rate,” says Peterson.

One reason that these whiskeys hold up is because the distillery used what today we would call “craft” or “artisanal” production methods, like jug yeast produced on-site, open fermentation vessels and use of spring water instead of municipal water.

While it’s easy to think of self-proclaimed “premium” spirits as a modern advertising invention, Van Winkle understood the yearning for them nearly a century ago.

“There are 10-cent cigarettes, 15-cent cigarettes and 20-cent cigarettes on the market, but the 15-cent and 20-cent cigarettes do not consider [that] they are in competition with 10-cent cigarettes,” Van Winkle explained in a 1949 speech to his distributors. By now, he had taken the nickname “Pappy” in his old age.

“We do not like the phrase, ‘We must meet the competition,’ unless you mean the competition of the very best and highest-priced brands on the American market,” he said.

This self-determined spirit is a major part of the appeal of Stitzel-Weller and, by extension, progeny like the Pappy Van Winkle label. These Bourbons speak to iconoclasm in a distinctly American accent.

“Stitzel-Weller is a slice of a vanished America where we made the best cars, did business with a handshake and liked richly flavored Bourbon,” writes spirits historian Joshua Feldman on his blog, The Coopered Tot.

Modern Family

Julian “Pappy” Van Winkle died in 1965. Seven years later, Stitzel-Weller and its brands were sold off. This was a “glut” era for Bourbon. Clear spirits like vodka dominated American palates, while plenty of great whiskey gathered dust on store shelves and sat in barrels in Kentucky warehouses.

In 1972, Pappy’s son, Julian Van Winkle Jr., started the Old Rip Van Winkle brand. During the sale of Stitzel-Weller, he secured the right to purchase their barrels to bottle as his own product, usually at seven and eight years old. Mainly, though, he made money by putting whiskey in gimmicky decanters.

When he died, in 1981, his son, Julian Van Winkle III, took over Old Rip Van Winkle Distillery. He was 32 years old with four young kids, and he needed to make money in an unfriendly Bourbon marketplace.

He continued to contract with the Stitzel-Weller Distillery, now owned by United Distillers, to produce Bourbon using his grandfather’s original wheated formula. He began to increase the age and proof of Old Rip Van Winkle, to 10 years and 107 proof, respectively.

By the early 1990s, he had acquired old enough stock to sell 12- and 15-year Old Rip Van Winkles. He was essentially a one-man show, but he was doing a solid job to revive the family name. He pounded the pavement around the country, just like his grandfather had done decades earlier.

Then came his breakthrough. In 1994, he had the gumption to release the world’s first 20-year-old Bourbon. With a stogie-smoking photo of his grandfather on the label, Pappy Van Winkle’s Family Reserve 20 Year was born.

“Julian the third is a true master of whiskey,” wrote Bourbon historian Michael Veach in 2016. That said, Julian III played a different game than every other brand, Veach says. He followed Pappy’s belief to always bottle less than you could sell.

“He had the advantage of purchasing only what he thought was good whiskey and passing on barrels below his standards,” says Veach.

Still, Julian III was scared to death that no one would buy this great Bourbon. At the time, no one had ever sold Bourbon this old. Ultimately, however, he had nothing to fear.

Pappy Van Winkle scored a then-unheard of 99 at the 1998 World Spirits Championships, and Julian III toured the country to host whiskey-paired dinners and win over chefs. Liquor stores and restaurants started to ask suppliers for Pappy Van Winkle’s Family Reserve by name, and other brands started to release older and pricier Bourbons in an attempt to compete.

Illustration by Eric DeFreitas

Millennial Reinvention

At the turn of the millennium, as Pappy Van Winkle’s success continued to grow, Julian III hit a snag. Stitzel-Weller, the source of the distillate upon which Pappy Van Winkle was based, ceased distilling operations in 1992. Soon, Julian III was going to be out of stock. He needed a new partner.

And so, in 2002, the distillation and aging of Pappy Van Winkle was taken over by Buffalo Trace in a joint partnership. Buffalo Trace would distill and age it to Julian’s specifications, and it would be bottled under the Pappy Van Winkle label.

Though the label says Old Rip Van Winkle Distillery, that’s merely branding. No physical Old Rip Van Winkle Distillery has ever existed. These new-breed Pappy Van Winkles started to hit shelves as early as 2011 in the case of Pappy 15, and as late as 2016 in the case of the 23 Year Old.

The taste was different from the Stitzel-Weller Pappy. It utilized different fermenters and stills, water sources, yeasts and aging locations. While some connoisseurs thought it wasn’t quite as good as it used to be, few thought it was inferior.

It hardly seemed to matter to the masses, however, who probably never knew who distilled Pappy in the first place. By this point, the chorus that sang the praises of Pappy Van Winkle had reached such a fever pitch, and prices had soared so high, that people could easily ignore that this wasn’t the same Bourbon that had won those awards.

It didn’t even matter that it wasn’t the same Bourbon that Pappy himself had once helped create and sell. It remained a big-ticket item. Countless fans were eager to procure a bottle, and any bottle with “Van Winkle” on it would do.

Arguably, that’s when Pappy fully transformed into “Pappy,” when the name on the bottle mattered far more than what was actually inside.

The rise of Facebook allowed strangers an unfettered grey market to sell Pappy for whatever the economics would bear. Though tens of thousands of new bottles are released each November, with the rather-reasonable price tag of $249 for the 23 Year, the secondary market continues to soar. That same 23 Year sells typically for closer to $2,000. Meanwhile, in 2017, a newly released Old Rip Van Winkle 25 Year Old sold for more than $16,000.

Mind you, the cognoscenti still seeks out Stitzel-Weller Pappy, which sells for quite a bit more than Buffalo Trace bottles.

As stores, bars and online sellers started to charge these inflated prices, shut-out consumers sought other Weller whiskeys. The economy brand uses the same wheat-based recipe, also distilled at Buffalo Trace, which puts the stench of Pappy on it. Pretty soon, even these lower- and mid-tier examples of “Poor Man’s Pappy” became tricky to find.

Now Pappy is clearly, most definitely, undeniably “Pappy.” That’s true whether it was distilled at Stitzel-Weller or Buffalo Trace, whether a Van Winkle oversaw its production or not, whether it actually even says “Pappy” on the label. (I’m done getting mad at people that call Van Winkle Special Reserve by that name).

If you want to own a bottle. you probably can’t, and if you want to try some, you probably won’t. But that’s only half the story.

Pappy remains exorbitantly expensive not simply because it’s perceived as rare, but because so many other, ethereal things have become attached to it. Pappy connects us to a sepia-toned image of American craftsmanship, when we expected to wait for the things we wanted. In a way, it’s a time machine back to an America that may or may not have ever existed: perfectly aged, beautifully packaged and nearly impossible to find.