For centuries, mathematicians and, later, statisticians, have found natural research and employment opportunities in the realm of insurance. By definition, insurance offers financial cover against unforeseen events that involve an important component of randomness, and consequently, probability theory and mathematical statistics enter insurance modeling in a fundamental way. In recent years, a data deluge, coupled with ever-advancing information technology and the birth of data science, has revolutionized or is about to revolutionize most areas of actuarial science as well as insurance practice. We discuss parts of this evolution and, in the case of non-life insurance, show how a combination of classical tools from statistics, such as generalized linear models and, e.g., neural networks contribute to better understanding and analysis of actuarial data. We further review areas of actuarial science where the cross fertilization between stochastics and insurance holds promise for both sides. Of course, the vastness of the field of insurance limits our choice of topics; we mainly focus on topics closer to our main areas of research.