Every Old Rip Van Winkle Whiskey, Ranked

For any bourbon aficionado, the name Pappy Van Winkle is synonymous with quality and scarcity. The brand undoubtedly produces some amazing whiskey, and any bottle you're able to obtain becomes a prized possession immediately. If that's your aim, this is the perfect list for you. Here, I'll rank all six bottles currently produced by Old Rip Van Winkle to see which one comes out on top. Along the way, I'll also look at the factors that helped make it such a revered whiskey brand.

All of these bourbons come with a premium price, especially on secondary markets. Due to this, I will be ranking them purely on taste. With personal preference playing a part, I'll also consider why one whiskey may rank higher on someone else's list. I've had the pleasure of enjoying most of these bottles, along with countless other whiskeys. This allows me to create a balanced list and one that is backed by many years of experience. All you need to do now is join me on this journey through some of the best whiskeys in the world.

Our journey through this great brand starts with the Van Winkle Special Reserve, also known as the 12-year or "Lot B." The name Lot B comes from when Julian Van Winkle III separated the 12-year-old barrels back in 1991. The limited stock of Lot A sold out quickly, with the greater volume of Lot B bottles taking a few years to sell. With some nostalgia now attached, all subsequent bottles were sold under the Lot B name. Before we go on, it's important to understand there is no bad whiskey here. Ranking these bottles goes from good to great, so even though it's ranked last here, the Van Winkle Special Reserve is still a very impressive whiskey.

With 12 years of aging, this bourbon offers plenty of complexity. Considering that extended aging, there is only a hint of oak on the nose, complemented by plenty of orchard fruits and cherries. Those fruits unfold on the palate along with a high level of sweetness. There isn't much warmth here, partly due to its low proof of 90.4. It's a deliciously smooth bourbon, and its rich caramel completes an enjoyable tasting experience. Those fruits carry to the finish and are joined by a subtle nuttiness. The tasting notes are a bit lighter than others on this list and don't deliver the same power, hence the lower ranking. It's still a brilliant bourbon, and you might even be lucky enough to pick up a bottle at your local Costco.

There is a line of thinking with whiskey that age equals quality. While there is some truth, the reality is much more complicated. Bourbon is aged in new oak casks, unlike Scotch, which is aged in used barrels. This aging in fresh casks means the wood more quickly influences the flavor. Simply put, a 23-year-old bourbon will have a much more notable oak influence than a 23-year-old Scotch. It's that extending aging that means the Family Reserve 23 Year expression often splits opinion. If you don't like a notable wood influence on your bourbon, then it's worth checking out some of the other Pappy bottles instead. For this reason, I didn't think it deserved to be ranked any higher.

Personally, I enjoy earthy flavors, but this bottle takes it to the extreme. The first thing you'll probably notice about this expression is its stunningly deep amber color. It hints at the complexity inside, and it doesn't disappoint. The nose isn't overwhelmingly woody, and you'll enjoy cherries and a range of other sweet notes. Oak dominates the palate initially, but then you'll start to pick out many of its other flavors, including a big hit of vanilla. As the palate develops, cherry and chocolate come to the fore. The finish is quite sweet and unsurprisingly long. Is it over-oaked? I don't think so. It's a well-balanced bourbon but may not suit everyone's tastes.

To further prove that age isn't everything, this delicious 10-year bourbon is a must-have. Cost isn't considered in these rankings, but a plus point is that this expression has the lowest suggested retail price of all Old Rip Van Winkle bottles. Despite having the youngest age statement on the list, it still has the craftsmanship and quality you expect from the Van Winkle name. Another bottle with a stunning copper color, you'll enjoy a simple yet elegant aroma once poured. Butterscotch is present throughout the tasting experience, and on the nose, that smell is joined by some caramel and a subtle spiciness of ginger.

The palate has more warmth than is hinted at with the nose. The spice notes develop, as you can pick out some cinnamon and nutmeg. There are also some other earthy flavors of tobacco and nuts. A full-bodied sweetness is added atop that foundation, and the caramel is particularly delicious. It doesn't have the depth of flavor to rank higher in this list, but it showcases those common bourbon notes above extremely well. At 107 proof, it has a bold character while still having that famous Pappy smoothness. This is a great place to start if you're looking for your first bottle of Old Rip Van Winkle. It's usually the cheapest and most accessible bottle and, as we've seen here, is still an incredibly good pour.

Here, the focus switches from bourbon to rye whiskey. Most bourbons use rye in the mash bill, but Old Rip Van Winkle uses wheat instead. That means this is not only the brand's lone rye whiskey but the only bottle to contain any rye. The irony, however, is that it doesn't taste like most other rye whiskeys on the market. Rye is known for giving a spicy quality to whiskey, and while that is evident here, it's far from overwhelming and instead gives it a comforting warmth. Another with a deep amber color, clove, cinnamon, and pepper hit you on the nose and immediately warm your soul. Balancing those aromas is a wonderful interplay of honey, caramel, and vanilla.

All of those tasting notes can be found on the palate. This is the type of whiskey that immediately washes away anything that may be on your mind as you get a wave of bold flavor that delights the senses. The rye grain shines through, and there is immense depth here but without being overpowering. Along with everything I've mentioned, there are also stone fruits, a subtle smoke, and nuttiness on the palate. Despite its high proof and intense flavor, it remains smooth with a velvety mouthfeel. The only reason it doesn't make the top two is that it may not be to everyone's tastes, but if you enjoy a rye influence in your whiskey, you'll love it.

It was exceptionally difficult to split the top two. Ultimately, I decided the expression taking the top spot had slightly more depth. However, it's fair to say this bottle is a strong contender for the best bourbon in the world aged 15 years or younger. This bottle is revered by whiskey enthusiasts worldwide, which is no surprise. The aroma has an array of enticing notes, with many berries and cherries, giving it a fruity smell. Along with an elegant sweetness, you also get a nice cedar aroma. Once you sip this famous bourbon, you'll soon see how it opens up with its tasting notes sitting within a luxurious 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.