Digital storytelling is the art of using digital content--still images, video clips, voiceovers, sound effects and music--to create short and compelling narrative movies. As an expressive medium in the art classroom, digital storytelling can be used to integrate subject matter knowledge and skills from many years of the school curriculum. If one wants to demonstrate that students are learning and applying twenty-first-century skills, there is no better method than an e-portfolio and a digital story, especially when the portfolio includes documentation of the process, reflection, and assessment. As the 2008-2009 Davis Digital Storytelling Challenge begins, it might be helpful for other teachers who are considering taking part to gain insight on how last year's winners produced their digital stories. In this article, Kirsten Smith, an art teacher of fourteen years from Washington Township High School in Sewell, New Jersey, gives some insight on what it takes to guide students through this project. (Contains 3 online resources.)