A comprehensive review of variable-length pendulums is presented. An attempt at a unique evaluation of current trends in this field is carried out in accordance with mathematical modeling, dynamical analysis, and original computer simulations. Perspectives of future trends are also noted on the basis of various concepts and possible theoretical and engineering applications. Some important physical concepts are verified using dedicated numerical procedures and assessed based on dynamical analysis. At the end of the review, it is concluded that many variable-length pendulums are very demanding in the modeling and analysis of parametric dynamical systems, but basic knowledge about constant-length pendulums can be used as a good starting point in providing much accurate mathematical description of physical processes. Finally, an extended model for a variable-length pendulum’s mechanical application being derived from the Swinging Atwood Machine is proposed. The extended SAM presents a novel SAM concept being derived from a variable-length double pendulum with a suspension between the two pendulums. The results of original numerical simulations show that the extended SAM’s nonlinear dynamics presented in the current work can be thoroughly studied, and more modifications can be achieved. The new technique can reduce residual vibrations through damping when the desired level of the crane is reached. It can also be applied in simple mechatronic and robotic systems.