A comprehensive study of the frictional chatter occurring during metal–cutting process is given. A general mathematical model of the machine–tool–cutting process is established, and then a high–accuracy numerical algorithm is developed. Next, a two–degree–of–freedom model of orthogonal metal cutting is examined. Then stochastic properties of the material being cut are introduced to reflect variations in the workpiece properties, in particular, in the cutting resistance. Nonlinear dynamics techniques, such as constructing bifurcation diagrams and Poincare maps, are employed to ascertain dynamics responses for both the deterministic and the stochastic model. Untypical routes to chaos and unusual topology of Poincare cross–sections are observed. The conducted analysis has provided some practical design recommendations. Finally, occurrence of chatter was investigated analytically.