A fundamental question has spawned fervent debates in classrooms and on Capitol Hill: How do we best educate children to be successful in a global, ever-changing world? Here we present the evidence that playful learning pedagogies not only promote important academic learning but also build the skills required for success in the 21st century. A brief review of current educational trends and their underlying philosophies is followed by the introduction to of the concept of “playful learning,” a teaching approach that uses free-play and guided-play activities to promote academic, socio-emotional, and cognitive development. The chapter then reviews correlational, observational, and experimental literature on playing around in school and offers suggestions and future directions for research in the emerging playful learning domain.