Julian P. “Pappy” Van Winkle was a travelling salesman for W.L. Weller and Sons. He created the Stitzel-Weller distillery by merging the A. Ph. Stitzel and Weller distilleries. His recipe for wheated bourbon—where wheat replaces rye as the second grain—was a massive hit. His son Julian Van Winkle II later revived the Old Rip Van Winkle brand using stocks from the distillery, which was sold in 1972 and closed by United Distillers 20 years later. Julian Van Winkle III turned to Buffalo Trace to continue production, first using the last casks of Stitzel-Weller, then Buffalo Trace's casks. Pappy Van Winkle is considered the best bourbon to have ever existed due to its recipe, quality and high age. The range includes bourbons aged from 10 to 25 years, and 13 year old and vintage rye whiskeys.

First released in 1998, Pappy Van Winkle 20 Year Old Family Reserve is one of the oldest and rarest expressions in the range. Named after Julian “Pappy” Van Winkle, the first in the family to turn his hand to producing spirits, it is one of the most prestigious bourbons in the world. The 20 Year Old became even more famous when 65 cases containing three bottles each were stolen from the distillery in 2013.