Dana Jester is more than just a talented painter — he’s a walking history book of the Bob Ross era and one of the most entertaining instructors you’ll ever meet. With roots that trace back to the days of Bill Alexander and early collaborations with Bob himself (you can even spot him in classic Joy of Painting episodes), Dana has long since developed his own powerful and detailed painting style.
Known affectionately as the “Wheeler Dealer,” Dana’s creative life extends beyond the canvas. He’s a collector and trader of all things unique — silver, marbles, rare coins, Bob Ross memorabilia — and he brings the same curiosity and sparkle to his painting as he does to every antique shop adventure. His signature subjects include expressive wildlife, Native American figures, and stunningly realistic animal portraits, all layered with a soft glazing technique that shows off his decades of experience.
Despite his incredible talent and deep artistic roots, Dana is one of the most approachable and hilarious people you’ll meet in a workshop setting. He makes the day fly by with stories, laughter, and unexpected tips that stick with you long after class. Currently based in Winchester, Indiana (with a brief stint in Arvada, Colorado, as fate would have it), Dana continues to teach, inspire, and uplift artists across the country — always with a joke in his back pocket and a paintbrush ready to go.
