Gentleman Jack Culture Shakers is a national program for one multicultural filmmaker and six multicultural bartenders to create short films showcasing how they are crafting culture as we know it. As a smooth and approachable Tennessee whiskey that utilizes a second charcoal mellowing process to achieve greatness, Gentleman Jack strives to embrace the creator in us all who takes the extra step to craft what’s real and strives to leave a legacy.

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“Directing and photography is a very intimate process for me. I connect in ways I don’t in my everyday life.” Exactly why Terrisha “TK” Kearse uses her lens for storytelling through photography and film to embrace humanity's inner worlds. She captures moments of joy and melancholy, distress and dignity, desperation and hope with a deep compassion for the external factors and hidden angst often obscuring our view of ourselves and each other.


Her portfolio of work spans feature film direction, fashion photography, directing music videos, portraiture, television, short film and travel photography. TK’s first feature “10-20” (renamed "Anger Has A Secret") won the 2009 HBO Award for Best Feature Film at the MVAAFF and was a finalist for the Best Feature Saatchi & Saatchi award. Her short film “The Mia Countdown” won the 2017 Jack Daniel’s Gentleman Jack Real to Reel local award for Best Short. TK’s photography also appeared in Season 2 of Black Lady Sketch Comedy on HBO.

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Myster Holliman

Oakland, CA | @thatmysterious1


Myster Holliman grew up in Hayward, Californina, near the San Francisco Bay area. His childhood years were filled with athletic endeavors and after high school, he attended California State University at Fresno to run track and field. After college graduation, Myster pursued a career in education and coached track at Fresno Christian High School. 


In 2013, he attempted to break the world record for longest distance traveled by skateboard—going coast-to-coast from Seattle to Miami Beach. After five months on the road, Myster returned home and gave bartending a try. While fine-tuning his skills, he eventually moved to Oakland for better career opportunities. Myster says the past five years have been an intense, but ultimately successful emergence into the man and bartender he is today.

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Jamie Clark

Las Vegas, NV | @spiritedjamie


Los Angeles native Jamie Clark made Las Vegas her new home in 2017. Jamie attributes her inspiration for crafting cocktails to the many cultures she encounters in her new hometown. To further elevate her expertise, she completed top industry courses including the Southern Glazer’s Wine and Spirits Academy of Mixology, Spirits and Fine Service, Advanced BarSmarts and the USBG Spirits Professional Course. Clearly Jamie’s found the right formula for success, in 2020 she was named “Most Creative Bartender” by the USBG Las Vegas chapter.

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Lauren Paylor

Washington, D.C | @lpdrinksdc


In 2010, Lauren Paylor left The Bronx to attend nursing school in Washington, D.C. However, her career trajectory shifted as she established a thorough understanding of F&B service. Lauren shared her knowledge with others as she strengthened her professional portfolio and mixology skills, ultimately placing top four at Diageo’s 2019 World Class US competition. She also holds titles for the 2019 Hardy Cognac Legend Competition and the 2020 Cognac Connection Competition. 


Lauren co-founded and owns Focus on Health, which supports health and wellness for F&B employees, and recently became R&D Production Chef. Her cocktails are often published and she was recently inducted into Bar International - Bar World 100 Most Influential Figures in 2021 and Wine Enthusiasts 40 Under 40 (2021). In addition, she is the newest U.S. inductee into the Dame Hall of Fame for Tales of The Cocktail (2021).

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Oscar Simoza

Boston, MA | @mustache.flex


Oscar Simoza arrived in Boston from Venezuela in 2006, immersing himself in the city’s lively hospitality industry. Starting in the dish pit, he worked his way to the bar, where he eventually began running his own bar program. By merging his love of spirits and socialization, Oscar has become one of Boston’s most recognized and adored bartenders.


Oscar’s passion for creating and presenting exciting cocktails often reflects his culture by integrating ingredients reminiscent of his native Venezuela. A positive force in the industry, Oscar brings his homeland’s high energy and warmth to guests every night he is behind the bar.

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Tiffany Hernandez

Los Angeles, CA | @mezcalmisstress


Native Angelino and Chicana Tiffany Hernandez’s family immigrated to the U.S. from Mexico and Guatemala. With six sisters, her mother, grandmother and cousins nearby, Tiffany remembers a childhood home filled with strong, feminine energy and always being the family’s traviesa kicking off the fiesta. 


Hostessing was her first hospitality gig, but Tiffany yearned for a more creative guest connection and secured a bar back job at 21. She worked at a neighborhood craft cocktail bar before moving to a high volume craft brewery. Moves to New York City and London offered extraordinary opportunities to hone Tiffany's mixology skills at some of the world’s top bars. Now she’s back in LA sharing her Latina heritage and lifting hermanos y hermanas in the industry.

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Stephen Simmons

St.Louis, MO | @konquered_balance


As owner of Konquered Balance, LLC (, certified personal trainer Stephen Simmons helps his clients balance life’s joys and responsibilities through customized fitness and nutrition plans. Stephen believes in daring to be different and taking risks no one else has.

He applies the same philosophy and discipline in his bartending, unapologetically emphasizing what he likes while simultaneously delighting customers through his mixology expertise. Stephen seeks to reveal something about the moment—whether the times we’re living in or a special occasion—as long as the outcome is fun and interesting.


Jack Daniel's Gentleman Jack 750ml Bottle

Inspired by the original gentleman distiller and our founder, Gentleman Jack undergoes a second charcoal mellowing to achieve exceptional smoothness. Its balanced flavor is perfect for celebrating life’s extraordinary occasions, plus all the moments along the way.


Watch Our Tasting Video 

Jack Daniel's Gentleman Jack 750ml Bottle