Over the past century, the Van Winkle name has firmly established itself as one of the most coveted in the whiskey world. Alongside icons like Macallan, Dalmore, Yamazaki, Dom Pérignon and Rémy Martin, Van Winkle represents more than just a high price—it is a guarantee of exceptional quality and craftsmanship. But how did a brand, named after a mythical figure who drinks whiskey and slumbers for twenty years, rise to become the most coveted bourbon in the world?
An important note before diving further into this historic brand is the difference between “Old Rip Van Winkle” and “Pappy Van Winkle”. Whilst both share the Van Winkle name, Old Rip Van Winkle was registered in 1895. The name is inspired by the story “Rip Van Winkle” by Washington Irving which follows a Dutch-American villager in colonial America who meets mysterious Dutchmen, imbibes their strong liquor and falls deeply asleep in the Catskill Mountain for 20 years. “Pappy Van Winkle” on the other hand was launched in 1994 by Julian Van Winkle III, Pappy’s grandson.
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This is one such example of the 1994-1999 green glass Pappy’s.
The earliest known examples of Old Rip Van Winkle are our three featured prohibition era medicinal pints. These were produced at RD#24, the Glenmore Distilling Company. This distillery was built in 1869 by Richard Monarch in Owensboro Kentucky. James Thompson purchased the Glenmore distillery in 1890 and operated the site until prohibition. Thompson was one of the few distillery owners to be granted a license to bottle whiskey. Based on historic mashbills from the United Distiller archive, these Old Rip Van Winkle bottlings were reportedly crafted from a four grain mashbill that included oats.
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These 1916 and 1917 vintage releases of Old Rip Van Winkle were bottled at a Missouri bonded warehouse operated by the Sunny Brook Distillery Co., a company later absorbed into The Whiskey Trust—better known in its subsequent form as National Distillers. It appears that the Van Winkle brand was owned by Glenmore, which likely contracted bottling operations to National Distillers’ Missouri facility. With the firm’s primary focus on Kentucky Tavern and Glenmore bourbons, Old Rip Van Winkle seems to have been a secondary priority.
Bottle design for prohibition era pints were usually a secondary concern, but the bottler for this batch of Old Rip Van Winkles truly went all out. The silver seal cap conceals a cork beneath, while the richly colored label showcases the iconic Old Rip character. Yet the most captivating feature is the intricate glasswork: Old Rip’s flowing beard extends from the back of the bottle to the front, creating a truly remarkable visual effect. These appear to be the only known Old Rip Van Winkle releases from this era, and such attention to detail in the glass suggests they were intended as a particularly special offering.
After Prohibition, the label fell silent. No Old Rip Van Winkle releases after this 1934 medicinal pint have been documented, and the brand would vanish for nearly four decades. It wasn’t until 1971 that the Stitzel-Weller distillery revived the icon, releasing a 7-year-old expression of Old Fitzgerald bourbon in a decanter shaped like Old Rip. It is unclear when the Old Rip Van Winkle brand shifted to Stitzel-Weller, but by 1971 it was being utilised for their wheated bourbons.
In 1972, Stitzel-Weller was sold to the corporate liquor firm Norton Simon. The distillery had struggled to remain profitable following Pappy Van Winkle’s death in 1965, with his son Julian II stepping in during one of the most challenging bourbon markets since Prohibition. After the sale, Julian fully revived the Old Rip Van Winkle label, sourcing wheated bourbon from his family distillery and releasing it in distinctive ceramic decanters. He would spend the following decade bottling these decanters before passing in 1981. Julian III, the grandson of Pappy, took over and moved operations to the Hoffman/Old Commonwealth distillery in 1983.
In the early 1980s, Kentucky liquor store owner Gordy Hue approached Julian III. Hue had previously worked with Julian II to source bottles and whiskey from Stitzel-Weller and envisioned creating a premium bourbon brand at a time when distilleries were closing across the nation. By the mid-1980s, he had designed a label and cognac-style bottle, which he presented to Julian III—marking the birth of the Van Winkle line of whiskies.
Over the next two decades, Hue and Julian III collaborated closely, launching the Van Winkle Family Reserve, A.H. Hirsch, and Pappy Van Winkle lines. Meanwhile, Julian III continued to produce Old Rip Van Winkle, offering everything from 4-year-old bourbon at 86 proof to 10-year-old bourbon at 107 proof. In 2003, Julian closed the Lawrenceburg site and partnered with Buffalo Trace, which began bottling his remaining barrels and supplying new wheated bourbon for his brands.
Today, Old Rip Van Winkle graces the 10-year-old expression in the annual Van Winkle releases. These bourbons are a collaboration between Julian Van Winkle III and Buffalo Trace, with all the whiskey produced at BT using their wheated mashbill. Julian and his son Preston personally select the barrels, ensuring consistent quality. By the 2010s, the Van Winkle name had entered the mainstream—everyone wanted a bottle of Pappy, or at least a Van Winkle. What began as a brand inspired by a whimsical “lazy Dutchman” has since become a symbol of the pinnacle of craftsmanship in the bourbon world.
