This chapter examines the multifaceted relationship between municipal police and the street culture that operates in advanced industrialized countries, such as the United States and Great Britain. In the process of doing so, the chapter asks and answers three principle questions: Why is understanding the relationship between police and street culture important? What are the factors that affect police–citizen encounters? And how do police officers learn the skills of the street? This analysis also examines when and how police become detached from the communities they serve and protect, and then reviews potential solutions to deal with this detachment. Finally, the chapter provides and analyzes possible methods that officers can use to improve how they deal with street culture. The authors accomplish this through a review of scholarly research on police activities, such as police behavior, patrol and discretion.