Whiskey Review: Five Brothers Kentucky Straight Bourbon Whiskey

The second stop on my recent Bardstown whiskey tour was at Heaven Hill Distillery, which was another gleaming modern facility surrounded by rickhouses as far as the eye can see. Our tour was the “Magic of the Mashbill” experience, and it started with a short video covering the history of Heaven Hill and the process used to make whiskey. We were then ushered into tasting room for tasting of Five Brothers Straight Kentucky Bourbon Whiskey, Elijah Craig Toasted Barrel, Henry McKenna Bottled-in-Bond, Pikesville Straight Rye Whiskey, and Elijah Craig Barrel Proof. Considering the Five Brothers whiskey is a distillery exclusive bottle, I thought I would grab one and give it the Thirty One Whiskey evaluation.



Established in 1935, shortly after the end of prohibition, Old Heavenhill Springs Distillery was founded by a group of investors in Bardstown, Kentucky. They were gambling on the idea that alcohol production would be a booming business and invested heavily in being one of the first companies to stand up and service that market. One of those investors was well known distiller Joseph L. Beam (first cousin to Jim Beam) who would also become the first master distiller of the facility.

As the years went on, the five Shapira brothers bought out all of the other investors to become the sole owner of the business and changed the name to “Heaven Hill Distillery,” which was a typo on the paperwork from the original Heavenhill distillery.  Despite being bought out, the descendants of Joseph Beam remain the master distillers of the facility to this day.

Their primary distilling facility burned down in 1996, destroying 90,000 barrels of whiskey and lighting the creek that feeds the distillery on fire for nearly two miles downstream. According to our tour guide, Bernadette, the fire melted 5 fire trucks and burned for nearly 4 days.  She also said that “the truth is agreed upon fiction,” so take that last fact as you will. 

The business survived and they purchased a new distillery in Bernheim from Diageo in 1999 where production now takes place, but all aging still takes place at the original Bardstown facility.

The 1935 bet has paid off — big time. Heaven Hill Distillery is currently the biggest family-owned distillery in the United States and the second largest holder of bourbon whiskey inventory in the world. Their flagship brands include Deep Eddy vodka and Elijah Craig, and their facility hosts the annual Kentucky Bourbon Festival


As a Kentucky Straight Bourbon Whiskey, this is required to start with a grain bill of at least 51% corn. According to a 2021 press release announcing the release of the bourbon, we know that this uses the traditional heaven hill mashbill of 78% corn, 12% malted barley, and 10% rye. The next step as always is that the grains are milled, cooked, and fermented to create a mildly alcoholic distillers beer.

That fermented mixture is then distilled, which ramps up the alcohol content and selectively captures the components and flavors of the spirit that the distiller wants, resulting in raw “white” whiskey. That newly made whiskey is then placed into new charred oak barrels for a period of no less than two years (as required for the designation of a Kentucky Straight Bourbon), and then the barrels are blended together to create just the right flavor profile.

This bourbon is a blend of five different bourbons ranging in age from five to nine years old. This blend is done to represent each of the five Shapira brothers. 

Once aged, the final step is bottling. As with the entire process to create this bottle, the final bourbon is bottled at 90 proof, “to reflect the initial proofs of Heaven Hill releases in the early stages of the distillery”.


Just like the distillation process, the bottle is an ode to the founding brothers. 

The bottle is relatively modern with a rounded square shape that flares slightly out as it goes up, leading to a sharp shoulder that tapers to a medium length neck. It’s topped with a wood and cork stopper, which is secured by blue and gold neck sticker. (What are these labels around the neck called? Do they have an official name? Let me know in the comments what you call them.)

The label is reminiscent of a old yellowed photo. It features the five Shapira brothers (David, Ed, Gary, George, and Mose) when they were in their late 20’s or early 30’s. The rest of the label has all of the legally required information on the front, and a short story about the brothers on the back. 

The color scheme works really well for me. It embodies the story that they are trying to tell, and I also appreciate that the shade of blue is very close to the old Chevrolet truck in the front of the visitor center. 



The Five Brothers bourbon has a sweet and approachable flavor profile. It begins with aromas of vanilla and brown sugar, with just a hint of caramel. While there are some subtle darker notes of oak and light tobacco, they don’t dominate the overall experience.

When sipping this bourbon neat, there is a bouquet of classic bourbon flavors. It starts with a mellow but very present caramel, along with brown sugar, maple syrup, and sweet vanilla notes. It’s not overly intense, but you can taste a layered flavor that most likely comes from the complex blending of various ages of bourbon. There’s also a very mild baking spice component, and a light touch of seasoned oak complements the sweetness. The intensity on the palate is well-balanced.

I enjoyed sipping this bourbon neat. It’s well executed, and is a very easy drinking bourbon — if anything, it’s on the sweet side without a lot of heat.

On Ice

When enjoyed on the rocks, as you might expect, some of the more pronounced flavors become a bit muted and toned down. Most notably is the sweetness, which mellows out significantly but thankfully not to the point where it isn’t enjoyable.It’s the difference between rich caramel and brown sugar to a Werther’s Original. Surprisingly, the baking spices and earthy oaky flavors are actually more prominent than before.

The resulting flavor profile is still enjoyable. I prefer it neat, but the richer notes that emerge on the rocks show promise for when we start building cocktails with this bottle of Five Brothers. 

Cocktail (Old Fashioned)

I personally prefer that my old fashioned to be made with a more robust bourbon rather than a sweeter bourbon. The depth of flavor is a great balance to the aromatics of the bitters, and makes for a more enjoyable experience in my opinion. The fact that when we tried this on ice, it mellowed out the sweetness and allowed the spices to shine made me excited for this cocktail. 

Thankfully, in this case, the expectations are in line with reality.  I think makes a damn good old fashioned.

The aromatic components of the bitters do a fantastic job balancing the oaky and spicy flavors, and the sugar helps to accentuate the mild yet rich sweetness from the bourbon. The resulting cocktail is a great old fashioned — so great, in fact, that it is featured bourbon in the house old fashioned at the Five Brothers Bar & Kitchen at the Heaven Hill distillery.

Fizz (Mule)

In order to make a good Kentucky Mule, a bourbon doesn’t have to be great — it just has to have enough depth of flavor to stand up to the ginger beer and bring something unique to the flavor profile (because if not, you might as well just use vodka and make a Moscow Mule). In this case, unfortunately, the resulting cocktail is just “meh”.

I was hoping for more, but this just seems to fall relatively flat. You can still pick up on some of the spice notes of the bourbon, but it’s pretty deeply buried under the other components in the glass. There is nothing that is overly complex, it’s mostly ginger beer, nondescript bourbon, and a twist of lime.


Overall Rating

For a flagship distillery product, this bourbon hits a lot of high notes. It’s fantastic taken neat or on the rocks, and it makes a solid old fashioned. Although it does not hold up as well across more robust cocktails, it’s still a well crafted ode to the founding brothers of one of the bigger distilleries. 

When released, this bottle was sold at $60 (2021) and is now selling for $80 (2023). (Inflation sucks, am I right?) Either way, while I think that this is something that is absolutely worth spending the money and picking up if you happen to be in the area. 

Five Brothers Kentucky Straight Bourbon Whiskey
Production Location: Kentucky, United States
Classification: Straight Bourbon Whiskey
Aging: No Age Statement (NAS)
Proof: 45% ABV
Price: $79.99 / 750 ml
Product Website: Product Website
Overall Rating:
All reviews are evaluated within the context of their specific spirit classification as specified above. Click here to check out similar spirits we have reviewed.

Overall Rating: 4/5
I think the Shapira boys would be proud of their namesake bourbon.


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