Meet Dwayne

Originally from New York, Dwayne Jackson is no stranger to high-stakes environments. A former football player at Freeport High School, Dwayne transitioned from the football field to the fast-paced world of stockbroking, landing a job at the notorious Stratton Oakmont—the firm made famous by The Wolf of Wall Street. From 1994 to 1996, Dwayne witnessed firsthand the wild, high-octane work culture of Wall Street, which now serves as comedic material for his stand-up performances.

After his time at Stratton Oakmont, Dwayne realized he wanted more out of life than the soulless grind of stockbroking. He pivoted into stand-up comedy, where his sharp wit and storytelling skills flourished. Known for sharing outrageous and humorous tales from his days as a broker, Dwayne’s unique blend of experience in both finance and comedy sets him apart.

Tired of the Wall Street hustle, Dwayne made the move to Key West to relax, let his hair down, and embrace the laid-back island lifestyle. He now works as the front desk manager at Southernmost Tattoo, where he brings his signature humor and positive energy to the shop. Whether he’s greeting clients, sharing stories, or cracking jokes, Dwayne ensures that everyone feels welcome and leaves with a smile.

Currently single and in search of a four-legged roommate, Dwayne enjoys the simple pleasures of island life, balancing his work at the shop with his passion for performing comedy and embracing the relaxed Key West vibe.