The tangential contact stiffness of cylindrical asperities is investigated using macro- and micro-mechanisms in this study. A microanalysis model is developed and the tangential contact stiffness of elliptically parabolic asperities on the contact surface is determined. The shape influence coefficient of the cylindrical contact is defined, and its rationality is evaluated. The influence of asperity distribution on the rough surface is determined, and the tangential contact stiffness macroanalysis model is constructed based on fractal theory. The mathematical expression to determine the tangential contact stiffness of the macroscopically cylindrical contact is generated, and the effects of influential factors on tangential contact stiffness are explicitly evaluated. Numerical results show that the tangential contact stiffness of asperities is determined by several factors, such as material properties, applied loads, fractal dimension, and surface shape.