Robust high-order optical vortices are much in demand for applications in optical manipulation, optical communications, quantum entanglement and quantum computing. However, in numerous experimental settings, a controlled generation of optical vortices with arbitrary orbital angular momentum remains a challenge. Here, we present a concept of “optical vortex ladder” for the stepwise generation of optical vortices through Sisyphus pumping of pseudospin modes in photonic graphene. The ladder is applicable in various lattices with Dirac-like structures. Instead of conical diffraction and incomplete pseudospin conversion under conventional Gaussian beam excitations, the vortices produced in the ladder arise from non-trivial topology and feature diffraction-free Bessel profiles, thanks to the refined excitation of the ring spectrum around the Dirac cones. By employing a periodic “kick” to the photonic graphene, effectively inducing the Sisyphus pumping, the ladder enables tunable generation of optical vortices of any order even when the initial excitation does not involve any orbital angular momentum. The optical vortex ladder stands out as an intriguing non-Hermitian dynamical system, and, among other possibilities, opens a pathway for applications of topological singularities in beam shaping and wavefront engineering.