For bourbon enthusiasts, Pappy Van Winkle is a name that represents both excellence and rarity. This renowned brand crafts exquisite whiskey, and any obtained bottle is instantly cherished. If your goal is to acquire such a bottle, this is your ideal guide. In this article, I’ll evaluate and rank the six bottles presently produced by Old Rip Van Winkle to determine the best one. We will also examine the elements that evolved it into a highly esteemed whiskey brand.

These bourbons carry a luxury price tag, particularly in secondary markets. Hence, they will be judged solely based on taste. Individual preferences will be considered, including why a particular whiskey might rank higher on somebody else’s list. Having had the opportunity to savour most of these bottles, along with numerous other whiskeys, equips me to provide a balanced, experience-based ranking. All you have to do now is to join me on this excursion through some of the world’s finest whiskeys.

Learn more: The 27 Best Bourbon Brands, Ranked

The exploration of this superb brand begins with the Van Winkle Special Reserve, affectionately known as the 12-year or “Lot B.” The label Lot B originated when Julian Van Winkle III differentiated the 12-year-old barrels back in 1991. The limited supply of Lot A was rapidly depleted, whereas the higher quantity of Lot B bottles took longer to sell. Owing to the nostalgia now associated, all subsequent bottles were marketed under the Lot B name. It’s essential to note that no whiskey here is substandard. The ratings range from good to fantastic, hence, even though the Van Winkle Special Reserve ranks last, it remains an admirable whiskey.

This 12-year-old bourbon is plenty complex. Despite its extended aging, there’s just a whiff of oak, accompanied by a plethora of orchard fruits and cherries. These fruits are also present on the palate, enhancing the high level of sweetness. The bourbon is not very warm, due to its low proof of 90.4. However, it’s a deliciously smooth concoction finished off with rich caramel, making the tasting an unforgettable experience. The fruity notes carry to the finish and meld with a slight nutty flavor. The tasting notes are slightly lighter than other varieties and lack the same strength, hence the lower ranking. Yet it remains a fantastic bourbon. Get lucky picking it up from your local Costco.

In the whiskey world, age is usually equated to quality. Whilst this holds some truth, the actual scenario is more complex. Unlike Scotch, Bourbon ages in new oak casks, impacting flavor faster. Thus, a 23-year old bourbon will have a more significant oak influence than a similar-aged Scotch. Consequently, the Family Reserve 23 Year expression often divides opinion. If strong wood flavors are not in your tastes, it’s wise to explore other Pappy bottles. This is the reason I didn’t rank it higher.

I have a preference for earthy tastes, but this particular bottle takes it overboard. The expression is instantly recognizable due to its deep amber color that suggests internal complexity. The aroma is not overwhelmingly woodsy, and you can savor cherries amongst other sweet notes. Initially, oak dominates the palate, but as you continue to taste, many other flavors like a strong hint of vanilla crop up. As the tasting progresses, cherry and chocolate flavors come to the forefront. The finish is pleasantly sweet and expectedly long-lasting. While not everyone may enjoy its extreme oakiness, I believe it’s a well-balanced bourbon.

Age is not the ultimate measure of a good bourbon, and this delicious 10-year-old variety is a must-have. The cost does not influence these rankings, but it’s a bonus that this expression has the lowest suggested retail price among all Old Rip Van Winkle bottles. Despite being the youngest on the list, it retains the sophistication and quality synonymous with the Van Winkle brand. This stunning copper-colored bourbon exudes a straightforward yet delightful aroma. Tasting this bourbon is a butterscotch journey, with traces of caramel and a ginger-like spiciness adding intrigue to its aroma.

The palate offers more warmth than the nose suggests. The spice notes evolve, revealing hints of cinnamon and nutmeg. Other earthy flavors like tobacco and nuts are also present. A rich sweetness overlays this foundation, with the caramel tasting especially delightful. Although it doesn’t boast a depth of flavor to rank higher on our list, it emphasizes the familiar bourbon flavors very effectively. This 107 proof bourbon offers a bold character while maintaining the well-loved smoothness of Pappy. It’s an excellent choice if you’re seeking your first bottle of Old Rip Van Winkle. It is generally the most affordable and obtainable bottle, yet remains a delightful pour.

Moving on, we turn our attention from bourbon to rye whiskey. While most bourbons incorporate rye in the mash bill, Old Rip Van Winkle employs wheat instead. This results in the brand’s sole rye whiskey and the only bottle to contain any rye. However, it doesn’t taste like the majority of rye whiskeys in the market. Rye is reputed for lending a spicy kick to the whiskey, but here, it offers a comforting warmth instead. The deep amber coloration, coupled with the immediate hit of clove, cinnamon, and pepper fragrances warming your soul, are balanced by delightful notes of honey, caramel, and vanilla.

These flavors can all be identified on the palate. This whiskey type prompts a wave of robust flavor that enlivens the senses and washes away anything presently occupying your mind. The rye grain is pronounced, providing immense depth without being overbearing. Additional flavors like stone fruits, a subtle hint of smoke, and a nutty touch can be detected on the palate. Despite the high proof and flavor intensity, it remains smooth with a velvety mouthfeel. It falls short of the top two mainly due to its particular taste, which may not appeal universally. However, if you’re a fan of the rye influence in whiskey, you’re bound to adore it.

Deciding on the top two was exceptionally challenging. I eventually concluded that the top-placed expression offered marginally more depth. Yet, this bottle is undoubtedly a strong contender for the world’s best bourbon aged 15 years or less. This bottle enjoys wide reverence among whiskey connoisseurs worldwide. The aroma unveils a variety of enticing notes, predominantly berries and cherries, lending it a fruity essence. Alongside a tastefully sweet profile, you’re also treated to a pleasant cedar fragrance. Sipping this famed bourbon unearths diverse tasting notes within a luxuriant, buttery mouthfeel.

You first get a wave of caramel and vanilla sweetness, which gently ebbs away to unveil its layers of complexity. Flavors of dark chocolate, leather, and roasted nuts dance along your tongue before you get a spicy warmth of cinnamon. Despite its age, the oak influence is relatively subtle and allows this expression to be remarkably smooth. The finish is long, with the earthy wood and spice notes continuing to the end. It’s an excellent bourbon with impressive consistency from one batch to the next. If you can get your hands on a bottle, this whiskey will be cherished on those special occasions.

The immense depth and complexity of this 20-year-old means that it just about secures the top spot. I said above about how the 23-year had a heavy oak influence. This bottle does too, but in a much more subtle way, making it a sure-fire winner for any bourbon lover. Old Rip Van Winkle bottles can sometimes be overhyped but this is a masterpiece of whiskey craftsmanship. It has that stunningly rich color many of these bottles share and that color starts a sensory journey. The next step is the nose, which is intoxicatingly inviting. The vanilla and caramel give it a graceful aroma before you can pick out a rich tapestry of dried fruits, cherries, cinnamon, and oak.

The smell promises an indulgent tasting experience, and that’s exactly what you get. The mouthfeel is rich and refined, allowing you to unveil the layers of flavor gently. Along with the notes on the nose, we get some brown sugar, dark chocolate, and toasted wood. The 20 years of aging give it a depth that doesn’t end there, and you can also enjoy leather, tobacco, and baking spices. The oak provides a rock-solid foundation to the flavor instead of dominating it. This expression is a testament to the artistry of the Old Rip Van Winkle distillery. Whenever you get the chance to taste it, this is a bourbon to be savored and cherished.

With most whiskey ranking lists, I usually consider price and availability. I didn’t do that here, as all Old Rip Van Winkle bottles can be hard to find and difficult to buy at their suggested retail price. Due to this, I only considered the tasting notes of nose, palate, and finish to rank these bottles.

I’ve had the pleasure of tasting most of these expressions over my many years of enjoying bourbon, including tasting different yearly batches. I have also enhanced my knowledge and experience with a wide range of views from bourbon experts and enthusiasts, along with the opinions of friends who have tasted Old Rip Van Winkle. This was to produce a list that, while filled with my opinion and tasting notes, also offers a more rounded view of how good these bottles are.

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