Pappy Van Winkle Bourbon Breakdown: Every Bottle Explained

Ask any bourbon drinker to list off a handful of bucket-list spirits they’re itching to taste, odds are Pappy Van Winkle will be included in the lot. This is true not only because of its rumored quality but due to a certain mysticism surrounding the brand name. That is to say, we’ve all heard of Pappy Van Winkle, but few of us have actually had the opportunity to try the famed bourbon – let alone get our hands on a bottle.

Boiled down, the story of Pappy Van Winkle, sold by Old Rip Van Winkle Distillery, culminated in a demand that exceeded supply by a longshot thus sending the value of each bottle into the stratosphere. Don’t get us wrong though, this isn’t over-hype, simply the mainstream market recognizing what bourbon collectors have known all along – that Pappy can very well be one of the best bourbons ever distilled. So where does it all start, and what’s the difference between the three heavily sought-after variants out there? The answers to these pressing inquiries can be found below.

Tasting Notes: What to Expect

Part of the reason Pappy draws such attention from the bourbon community is its exquisite taste. This partially stems from the inclusion of wheat over barley or rye in the mashbill – combined with the over-the-top aging process. It’s also worth noting that in order to attain this ideal profile, you have to take into account the angel’s share (whiskey that evaporates throughout the aging process) and the devil’s cut (bottom-barrel whiskey that’s left behind) resulting in only a fraction of usable whiskey per batch, which continues to get smaller the more it’s aged.

It’s this process that allows Old Rip Van Winkle distillery – a distillery that doesn’t actually produce its own whiskey – to have initially taken donor batches from Stitzel-Weller and now from Buffalo Trace – and produce a fine bourbon each and every time.

Old Rip Van Winkle 10 Year

Although it only retails for $70, this 10-year-old Old Rip Van Winkle bourbon will still put you out about a grand if you want to try it out. Featuring a rifled wizard on the label, this whiskey is tied with the 15-Year Special Reserve for the brand’s highest-ABV expression at 107 proof –– nearly cask strength if it weren’t for the touch of water added to bring out the flavors more (NOTE: the 15-Year’s 107-proof is cask strength). If you’re looking to minimize your spending while still claiming a bottle of Pappy’s on your shelf, this is the way to go. And you won’t be sorry; tasting notes are still exceptional with dried fruit, toasted nuts, and a finish of peppery spices and floral honey.

Van Winkle Special Reserve 12 Year

At just 90 proof, this 12-year-old bourbon is a lot easier to drink. If you were ballsy enough to throw a shot of Pappy’s into an old fashioned (and skilled enough to do it right), this would be the one to do it with. With less of the oak tannins and spice that come with a higher ABV, it’s easy to drink and typically more accessible than its younger, 10-year-old brother. However, aged for a couple of extra years, this bourbon is still fantastic, which is why it pulls in around $1,000 on the secondary market.

Pappy Van Winkle Family Reserve 15 Year

The youngest of the Family Reserve lineup, this 15-year option still boasts one of the smoothest mouthfeels around and tied with the 10-year for the highest proof (clocking in at barrel proof of 107). Each batch is aged in charred oak barrels for 15 years, undisturbed, before they’re bottled and released to the public. Expect smooth notes of cooked sugar, dried fruit, spices and oak tannins with each sip – complemented by the caramel flavors that remain present from beginning to end.

Pappy Van Winkle Family Reserve 20 Year

Earning a miraculous 99/100 score by the Beverage Testing Institute back in 1996 (the highest rating they’ve ever given) this 20-year-old bourbon is certainly a one-of-a-kind spirit held in high regard by celebrities and bourbon collectors the world over. Arguably more popular than its older 23-year counterpart, it’s both sweet and complex – brushing aside the notion that a two-decade-old bourbon can be overly woody and unbalanced. Instead, it’s rumored this fine spirit boasts an almost cognac-like flavor and silky smooth mouthfeel featuring notes of dried fruit and honeyed oak.

Pappy Van Winkle Family Reserve 23 Year

The rarest of the rare, the 23-year variant is one that’s heavily sought after and is most likely the bottle your local collector covets the most. Most certainly a bucket-list bourbon, the price point of these bottles absolutely skyrockets from its MSRP due to very limited supply and astronomical demand. However, if you’re lucky enough to get your hand on a bottle, you’ll find a prominence of dark fruits, dark spices, coffee notes and browned butter, charred oak and even star anise present in its dark and dynamic profile. Our suggestion? Drink it neat or don’t drink it at all.

Van Winkle Family Reserve Rye

Many people don’t realize that Pappy has a rye whiskey counterpart to its wheated bourbons, even though it’s just as popular amongst rye aficionados. If you’ve ever tasted rye, you’ll notice a more spice-forward, less earthy profile compared to high-wheat expressions. Aged for 13 years, which is very high for a rye whiskey since the grain doesn’t typically require as much aging, this Van Winkle Family Reserve bottle uses at least 51% rye in its mash (which is the legal minimum) and soars with a profile featuring honey, tobacco, and caramel.

History: Pappy’s Persistence

We can trace the humble beginnings of Pappy Van Winkle back to 1893 when Julian “Pappy” Van Winkle, Sr. (the bourbon’s obvious namesake) was first hired into a sales position for the W.L. Weller & Sons wholesale liquor distributors. After 15 years of employment and knowledge gained through his tenure there, he and Alex Farnsley (another Weller salesman) purchased the firm and in 1910 acquired the A. Ph. Stitzel Distillery in Louisville, Kentucky that had been around since 1872.

Now, with both production and distribution under one roof, Stitzel-Weller introduced, among others, the Old Rip Van Winkle brand just before Prohibition effectively put a temporary hold on the market. It was then in 1935, coinciding with the Kentucky Derby, that Stitzel-Weller Distillery opened just outside of Louisville, Kentucky and became known for their “wheated” bourbon recipes. For reference, these bourbons utilize the wheat grain instead of rye in the mash rendering a smoother and softer taste.

“We make fine bourbon. At a profit, if we can. At a loss, if we must. But always fine bourbon.”

– Julian “Pappy” Van Winkle

With a successful business in place, Pappy – the first of four generations of Van Winkle bourbon distilling – remained involved with his distillery until his passing in 1965 at the age of 91. Afterwards, Pappy’s son, Julien Jr. ran the day-to-day operations at Stitzel-Weller up through 1972 when it was effectively sold off. However, not before he could effectively resurrect the Old Rip Van Winkle brand in 1971. Using old whiskey stocks, Julian Jr. was able to breathe new life into the pre-Prohibition brand up until his death in 1981.

From here, Julian Van Winkle III took over the Old Rip Van Winkle brand and purchased the Hoffman Distillery in Lawrenceburg to store and bottle Van Winkle whiskey. A wrench was thrown into this equation, however, when in 1992 Stitzel-Weller – one of Julian III’s primary suppliers – shut down for good. So, what later resulted was a partnership with Buffalo Trace in 2002. Following this merger, a point of contention for some bourbon collectors arose out of worry that a different donor whiskey could have an adverse effect on the final product down the road. This, of course, has yet to be proven true.

Nevertheless, such speculation and uncertainty into the future of Pappy no doubt adds to the bourbon’s allure to this day – inevitably enhancing the secondary resale value of each available bottle.

The Bottles: The Old Rip Van Winkle Distillery

As far as the bottles are concerned, Old Rip Van Winkle Distillery offers five different bourbons and one rye for the market. These are categorized as 10, 12, 15, 20, and 23-year-old bourbons and one 13-year-old rye. From here, the oldest three (that is the 15, 20, and 23-year-old options) are all categorized under the Pappy Van Winkle Family Reserve name and for this post’s sake, referred to as “Pappy” from a branding standpoint. That being said, whenever you hear someone referring to “Pappy Van Winkle bourbon” they’re referencing one of these three bottles. All of which bears an image of Julian “Pappy” Van Winkle smoking a stogie on the bottle.

So what do these bourbons have in common? Well, thanks to earlier established recipes by Pappy himself, everything sold by the Old Van Winkle distillery are wheat-stye bourbons. In case you’re wondering what makes a ebourbon wheat-style, consider the mash, which by law must contain at least 51 percent corn and the rest some combination of rye and barley. Here, though, wheat replaces the rye in the grain build, which results in a smoother product overall.

A Sudden Spike In Interest

As you can see, interest began its impressive upward trajectory around 2011. And with a limit of only 7,000-8,000 cases a year (for reference Jim Beam produces upwards of 8 million cases a year), this demand forces the value of Pappy on the secondary market to skyrocket.

As for the high demand, there are few high-end bourbons out there that are as revered as Pappy. But why? The demand is quite remarkable actually, with bottles selling on the secondary market for as high as 1,000% of the retail price thanks to limited quantities and soaring interest. Interestingly enough, this wasn’t always the case. For instance, a rudimentary search on Google Trends shows the search volume of Pappy Van Winkle taking off around 2006, increasing practically every year since – which happens to be coordinated somewhat with the growing interest in bourbon overall during that time frame.

It also doesn’t hurt Pappy’s reputation that the bourbon has enjoyed a significant amount of press, testimonials (from the likes of Anthony Bourdain and David Chang), and a myriad of awards from various competitions around the globe. It’s also very rare to find wheated (or any) bourbons aged 15 years or more which truly sets Pappy in a league of its own.

How To Actually Shop for Pappy’s

You may notice the wide discrepancy between the suggested retail prices and the market value and wonder why it’s so difficult to secure the former. Over the years, hunting for Pappy’s has become an actual sport. However, if you don’t have good connections with a distributor or liquor store owner, you’ll have to settle for paying significantly higher prices than the suggested retail (re:it’ll be expensive). Liquor stores get a limited amount of bottles for each year’s releases and often hold a raffle so their customers have a fair chance of being able to purchase their own for a reasonable price.

That said, there are some tricks of the trade. For one, shops in larger, more populated cities will usually secure more bottles than ones that get less foot traffic. Likewise, it doesn’t hurt to be loyal to your favorite shop. If you shop there frequently and get in good with the owners and managers, they may give you the first crack at new shipments that come in. Also know that new Pappy’s tend to come in every year around October or November, so mark your calendars and stay informed from Buffalo Trace.

It’s also important to note that not every seller is an honest one. Fake Pappy’s do exist, which is why you should stick to shops and websites that you trust and have a good reputation.

The Best Wheated Bourbons

It’s understandable if Pappy’s is way too pricey for your bank account. That’s why we’ve compiled a guide to the best wheated bourbons that serve as a Pappy’s alternative.