Mathematics is a discipline that has significantly advanced through the use of digital technologies with improved computational, graphical, and symbolic capabilities. Digital videos can be used to present challenging mathematical questions for students. Video clips offer instructional possibilities for moving students from a passive mode of watching to active exploration of mathematical ideas. Video clips (short excerpts from movies, television shows, professionally prepared educational videos, or personally created videos) can be used to introduce new mathematical concepts and processes; explore mathematics in nature, art, or other contexts in the real world; and engage students in expressing their mathematical understandings as they think about what has been said or displayed. YouTube is a rich source for video clips and short movies that will challenge students to watch carefully and engage in mathematical thinking. Analysis is at the heart of reasoning in mathematics. Students need experiences that guide them as they learn to reason mathematically. They need opportunities to make conjectures based on their analyses and to communicate the thinking that directs them toward these conjectures. Engaging students in analysis of events in video clips is one way of providing these important experiences. Integrating digital videos with other media, such as Geometer's Sketchpad, spreadsheets, calculators, and virtual manipulatives, affords students many opportunities to create, use, and make sense of multiple representations of mathematical ideas. Technology is essential in teaching and learning mathematics; it influences the mathematics that is taught and enhances students' learning. In this article, the authors describe how digital videos can both enhance students' learning of mathematics and engage students in mathematical thinking. (Contains 3 online resources.)