Today, schools are actively looking for new ways to enable their students to develop storytelling skills. These skills should empower children and young adults to practice collaborative learning on many levels, from reading and writing to painting and project management. In this framework, digital painting provides educators with innovative avenues to develop storytelling skills. These tools can awaken and sustain the interest of students of various ages in many arenas such as creative play, art, calculus, history, science, biology, and computer use. Today, a new breed of digital painting tools exist that allow students to strive toward their potentials by permitting the exploration of a wide range of educational topics via storytelling and digital painting. This article offers suggestions on how educators can incorporate digital painting and storytelling in the classroom today.