So, you want to spend more than $100 on a bourbon. Great! This is your right. (If you haven’t tried the army of great bourbons for less than $50 or $25, you should probably start there first.) There are loads of “high-end” bourbons to choose from. Since the bourbon boom in the early 2000s, a whole marketplace of very expensive bourbons has exploded, despite dismay from thrifty collectors, incredulity from the old guard and downright legal actions against the burgeoning black market.
Here’s what you need to know: at this price point, buying bourbon becomes a lot more like buying collectible Air Jordans: it’s a lot more about supply and demand than it is quality and value for your dollar. But fear not. These are the ones we’d give an arm and a leg for, if we decided to splurge.
The Pappys

Distillery: Buffalo Trace
Proof: varies
Price: $250 – $2,000+
The Legends: The “Pappy Suite” is the most recognizable name in expensive bourbon. It was first sold by its namesake’s son and grandson in the 1980s, who had bought up sweet barrels from shuttered distilleries like Stitzel-Weller; in the early 2000s, just after its hype train really started rolling, the Van Winkles turned over its production and bottling to Buffalo Trace. Today they sell five consistently (plus a well-loved rye): the 10- and 12-year olds, which are technically not “Pappy” but are still pretty great, and the 15, 20, and 23 year old versions. Good luck finding those last three for under a grand.