The 21 Most Important Bourbons of All Time

Determining the most important bourbon of all time raises a plethora of questions around the meaning of significance itself. According to Merriam-Webster, it’s defined as “marked by or indicative of significant worth or consequence.” With this lens, it’s clear that worth doesn’t strictly equate to price. Surprisingly, many of the most impactful bourbons remain humble, often sitting on a bottom shelf for a mere $30.

This list celebrates bourbon bottles that hold historical importance, capturing expressions that have transformed the industry, set new standards, or altered its very landscape. While some of these bottles are rare or even lost to time, others remain available for purchase. What resonates across all entries is their undeniable influence on the bourbon world.

A selection of iconic bourbon bottles that shaped history.

21. Michter’s Toasted Barrel Bourbon

ABV: 45.7%
Average Price: $140
Why It Matters: Michter’s Master of Maturation, Andrea Wilson, revolutionized the industry with her innovation of “toasted barrel bourbon.” This process involves holding a barrel over a flame without charring it, thereby unlocking a unique range of wood sugars that enhance flavor complexity.

20. Angel’s Envy Bourbon

ABV: 43.3%
Average Price: $42
Why It Matters: While not the first to create finished bourbon, Angel’s Envy became the first brand to make an evergreen core expression of finished bourbon, effectively changing consumer expectations and industry standards.

19. A.H. Hirsch 16-Year Bourbon

ABV: 45.8%
Average Price: $5,000
Why It Matters: The Gold Foil edition of A.H. Hirsch 16-Year Bourbon is celebrated by whiskey aficionados for its unique quality, made famous by writer Chuck Cowdery, who penned a book devoted to its legacy.

18. Four Roses Single Barrel Bourbon “Goykh Smash”

ABV: 60.3%
Average Price: ??
Why It Matters: This bourbon is credited for introducing private label stickers, also referred to in the community as “tater stickers,” marking a significant moment in bourbon marketing.

17. Parker’s Heritage Collection 1st Edition Cask Strength

ABV: 63.7%
Average Price: $5,800
Why It Matters: Uniting bourbon with philanthropy, Parker’s Heritage Collection was crafted to honor Parker Beam’s enormous contributions, helping to reshape the continuing narrative of bourbon and charity.

16. Wild Turkey 12-Year 101 Bourbon “Cheesy Gold Foil”

ABV: 50.5%
Average Price: $1,800
Why It Matters: Wild Turkey 101 played a crucial role in sustaining the bourbon industry through difficult periods in the 70s and 80s, exemplifying resilience in a challenging market.

15. Willett Family Estate 28-Year-Old Bourbon Barrel #1056

ABV: 64.4%
Average Price: $11,875
Why It Matters: Renowned for their vault of incredibly aged whiskey, Willett Family Estate has cemented its status as a legendary name in bourbon.

14. Weller Special Reserve Wheated Bourbon

ABV: 45%
Average Price: $97
Why It Matters: Frequently cited as the first significant wheated bourbon on the market, Weller opened new avenues for consumers seeking softer, sweeter flavors in their whiskey.

13. Evan Williams Bourbon

ABV: 43%
Average Price: $28
Why It Matters: Coming from Kentucky’s first legally registered commercial distillery, Evan Williams Bourbon holds historical significance as a pioneer of the bourbon landscape.

12. Jim Beam Distiller’s Masterpiece (1999)

ABV: 49.5%
Average Price: $1,800
Why It Matters: This release marked a turning point as one of the first super-premium bourbons, establishing a new tier for bourbon quality and desirability.

11. Smooth Ambler Old Scout Single Barrel Bourbon

ABV: 55.9%
Average Price: $300
Why It Matters: The arrival of these sourced expressions from MGP set the bourbon market ablaze, paving the way for a new appreciation of sourced whiskies.

10. Old Crow Chessman

ABV: 43%
Average Price: $2,300
Why It Matters: The Chessman series from Old Crow symbolizes crucial industry developments and innovations that have occurred over the decades.

9. Eagle Rare 25

ABV: 50.5%
Average Price: $45,000
Why It Matters: Notable for being a hyper-aged bourbon, Eagle Rare 25 has garnered widespread acclaim among collectors and aficionados alike.

8. Blanton’s Single Barrel Bourbon

ABV: 46.5%
Average Price: $110
Why It Matters: Often hailed as the first single-barrel bourbon to gain widespread recognition, Blanton’s set a precedent for the future of bourbon offerings.

7. Old Forester President’s Choice

ABV: 60%
Average Price: $1,600
Why It Matters: Known as the world’s first single-barrel bourbon, Old Forester’s President’s Choice set new benchmarks for quality and individuality in the bourbon sector.

6. Pappy Van Winkle 20-Year Bourbon

ABV: 45.2%
Average Price: $3,000
Why It Matters: As the first release in the esteemed Pappy Van Winkle lineup, it commands respect and reverence in the world of bourbon.

5. Jack Daniel’s Tennessee Whiskey

ABV: 40%
Average Price: $27
Why It Matters: Popularizing the Lincoln County Process, Jack Daniel’s set essential standards for the Tennessee whiskey industry and beyond.

4. Very Very Old Fitzgerald Blackhawk Edition

ABV: 60.5%
Average Price: $80,100
Why It Matters: This limited release reached new heights in the auction world, becoming the highest-priced bourbon sold at auction in 2024.

3. Old Forester Bourbon

ABV: 43%
Average Price: $19
Why It Matters: As the first commercially available bourbon sold in glass bottles, Old Forester changed the way whiskey was sold and marketed forever.

2. Maker’s Mark Bourbon

ABV: 45%
Average Price: $30
Why It Matters: By emphasizing tourism and introducing its emblematic red wax seal, Maker’s Mark revolutionized the bourbon industry and the consumer experience.

1. Booker’s Bourbon

ABV: Varies by batch
Average Price: $120
Why It Matters: Lauded as the first commercially available cask-strength bourbon in 1988, Booker’s set a high bar for bourbon enthusiasts everywhere.

Each of these bourbons not only reflects a moment in time but also continues to shape the evolution of whiskey culture across the globe. As the bourbon landscape expands, the innovations and milestones of these bottles serve as a reminder of the craftsmanship and creativity that define this celebrated spirit.