In this chapter, we will first address general issues of the art and craft of modeling-contents, concepts, methodology. Then, we will focus on modeling in contact mechanics, which will give the opportunity to discuss these issues in connection with non-smooth problems. It will be shown that the non-smooth character of the contact laws raises difficulties and specificities at every step of the modeling process. A wide overview will be given on the art of modeling in contact mechanics under its various aspects: contact laws, their mechanical basics, various scales, underlying concepts, mathematical analysis, solvers, identification of the constitutive parameters and validation of the models. Every point will be illustrated by one or several examples.