Five Brothers Bourbon

Every distillery has a story, but Heaven Hill’s is one of those rare ones that feels genuinely woven into the fabric of Kentucky bourbon. Five Brothers Bourbon leans into that heritage with a name that honors the Shapira brothers, the family who founded Heaven Hill back in 1935. The bottle itself doesn’t scream for attention — it doesn’t have to. What’s inside does the talking, and it speaks with the kind of easy confidence that only comes from decades of knowing exactly what you’re doing.

A Toast to Heaven Hill’s Roots

Heaven Hill’s story begins in 1935, just after the repeal of Prohibition, when the Shapira family partnered with distiller Joseph L. Beam to found what was then called Old Heavenhill Springs Distillery in Bardstown, Kentucky, named in honor of the farmer who owned the property – William Heavenhill. Unfortunately, when the government office recorded the name, they added a space and it became the Old Heaven Hill Springs Distillery. 

With no brands, no inventory, and no guarantees, the Shapiras opened their doors during one of the toughest economic periods in American history — yet their commitment to quality and family stewardship set the foundation for what would become one of the country’s most respected bourbon producers. Those early decades were defined by resilience, steady growth, and a dedication to crafting traditional Kentucky whiskey.

Over the years, Heaven Hill evolved from a modest post-Prohibition operation into the largest independent, family-owned spirits company in the United States, producing iconic brands like Elijah Craig, Evan Williams, and Larceny. Even after a devastating distillery fire in 1996, the company rebuilt, expanded, and continued aging whiskey in Bardstown while distilling at their Bernheim facility in Louisville. Today, Heaven Hill stands as a pillar of bourbon heritage — a family-run operation that has weathered nearly a century of change without losing sight of the craftsmanship and values that shaped its beginnings.

Tasting

Five Brothers is packaged in a short, rounded bottle and carries the iconic Heaven Hill mash bill of 78% corn, 10% rye, and 12% malted barley. The finished product is a blend of bourbons aged five, 6, 7, 8, and 9 years, representing each of the founding Shapira brothers. It is bottled at 90 proof reflecting early Heaven Hill releases.

Eye: In the glass, Five Brothers Bourbon shows off a reddish-copper hue that immediately catches the light. Give it a swirl and you’ll see evenly spaced medium legs slowly making their way down the sides of the Glencairn. It’s a promising start — rich color, steady structure, and a look that suggests both maturity and balance.

Nose: The nose opens with a classic Heaven Hill sweetness of vanilla and brown sugar. But it doesn’t stop there. A bright pop of citrus — think orange peel — lifts the aroma and keeps it from feeling too heavy. Then comes a cozy wave of apple fritter, warm and doughy, followed by a grounding note of toasted oak, like stepping into a rickhouse on a cool morning. It’s layered, inviting, and wonderfully aromatic.

Palate: The first sip is where Five Brothers really shines. It’s incredibly smooth, almost silky, with a creamy mouthfeel that coats the tongue in the best way. The flavors echo the nose — vanilla, spice, and oak — but they come together with a cohesion that feels effortless. This is very well-balanced and delightful.

Overall: This is super pleasing. Originally seen only at the Heaven Hill Distillery, I’ve started to see it on store shelves. Five Brothers Bourbon is a heartfelt tribute to Heaven Hill’s origins, but it’s also a genuinely enjoyable pour in its own right. It’s approachable without being simple, flavorful without being flashy, and smooth without sacrificing character. If you’re a fan of classic Kentucky profiles with a creamy texture and a warm, spiced finish, this bottle deserves a spot on your shelf.