DTLA Happiest Hours: The Legend of Old Hillside Bourbon Company

Old Hill SideBourbon

On the day Jesse Carpenter conceived his first vision of the Old Hillside Bourbon Company, he and his childhood friend Brian Burton were sharing the roaring excitement of a day at the Kentucky races.

Before day’s end, the pair would bet on the odds of establishing a first-rate whiskey brand that would pay homage to the black equestrians of yesteryear, telling their magnificent triumphs with every sip.

When Jessie and Brian invited their childhood friend, Courtney Tucker, at first Courtney thought the two were joking, but with reality settling in, came the first batches of the Old Hillside Bourbon Company. Enter Emmanuel Waters, officially brought on board by cousin Courtney, who sought out his contract negotiation background in Silicon Valley.

Photo courtesy Old Hillside Bourbon

Furlong, Brian Burton, Jesse Carpenter, Courtney Tucker, and Emmanuel Waters became grand prize winners across the board: with an exciting brand that promises high-quality whiskey, proudly celebrates black history, and promotes positive changes for the community.

Old Hillside Bourbon Company is a “lifestyle brand,” and it’s not just about looking good and
making money, but about making a difference.

-Courtney Tucker spoke of the group giving back to their alma mater and sponsoring community athletic teams for the youth.

There’s a variety of Old Hillside Bourbons
to choose from, ranging from traditional floral to fruity whisky refinement.

Each Old Hillside Bourbon hand-crafted bottle comes with a bit of corked history at the entrance. A rustic paper label announces each volatile note of this bold Kentucky whiskey stored behind it. ‘The Last Rye’d’, this 104 proof, five-year-old, barrel-aged straight rye whisky takes on a floral approach with strong hints of caramel, vanilla, mint, and slight notes of nutmeg, and cinnamon. The Last Rye’d won Double Gold in the San Francisco Spirits Competition. This particular bottle is the Mount Rushmore of African-American Horse Race Jockeys, with an olden-day collage of the riders making up the label that marks a taste of vigor likened to any horse at the starting gate.

Fact: Few people know that in the first Kentucky Derby, 13 of the 15 riders were African-American. In fact, black jockeys won 15 of the first 28 derbies, dominating the sport before the Jim Crow laws came into effect.

Alonzo Clayton was the youngest black jockey to win the Kentucky Derby. Oliver Lewis won the first Kentucky Derby in 1875. James “Soup” Perkins began riding at eleven years old and led a successful career in horseback riding. And there are others, including Isaac Murphy, who was one of the best jockeys of all time. These legends left their hoofs in the tracks of history from 1875 to 1903. However, the Jim Crow laws, segregation, difficulty obtaining licenses, and threat of bodily harm left the Kentucky Derby without black jockeys from 1921-2000. However, the legacy of these black jockeys will not be forgotten, especially thanks to Old Hillside Bourbon.

With even more history behind each variety, The Hornet’s Nest, winner of the Silver Medal at the 2023 San Francisco Spirits Competition is a limited-release bottle to commemorate the centennial celebration of Hillside High School (1943–2022), where the team first met. This bourbon whiskey offers a distinct sweet vanilla and apple taste and finishes with the slight subtlety of oak flavors.

The company intends to grow exponentially within the coming years and establish roots in the city by expanding its ranking at bars, restaurants, hotels, events, and through earned publicity. The brand has already been featured on NBC LA and has a celebrity ambassador attached to it.

Last year, downtown Los Angeles hosted an event called Lightning Machine, where the quartet met actor Orlando Jones, known for his work on MADTV, American Gods, and being the liveliest spokesman for 7UP back in the 90s. After a few sips and conversations, Orlando Jones joined the group as the official spokesperson for Old Hillside Bourbon.

Old Hillside Bourbons are distilled in Kentucky because of the natural mix of climate conditions and pure limestone water that give their bourbon layers of taste that evolve and resonate with elegant finishes. Today, The Old Hillside Bourbon Company’s products are right on track, and can be found on their website and at other online retailers such as; Taste Select Repeat, Reserve Bar, Total Wine and BevMo! Also, the website features a location tool that can be utilized to find where you can purchase the product closest to you and tons of recipes. www.oldhillsidebourboncompany.com

Author: Keri Freeman

Military mom and proud parent, artist, writer, musician and film maker. Cocktail connoisseur. Publisher of DTLA Weekly.