A modified discontinuous deformation analysis (DDA) algorithm was proposed to simulate the failure behavior of jointed rock. In the proposed algorithm, by using the Monte-Carlo technique, random joint network was generated in the domain of interest. Based on the joint network, the triangular DDA block system was automatically generated by adopting the advanced front method. In the process of generating blocks, numerous artificial joints came into being, and once the stress states at some artificial joints satisfy the failure criterion given beforehand, artificial joints will turn into real joints. In this way, the whole fragmentation process of rock mass can be replicated. The algorithm logic was described in detail, and several numerical examples were carried out to obtain some insight into the failure behavior of rock mass containing random joints. From the numerical results, it can be found that the crack initiates from the crack tip, the growth direction of the crack depends upon the loading and constraint conditions, and the proposed method can reproduce some complicated phenomena in the whole process of rock failure.