The breakup of viscous liquid threads is governed by a complex interplay of inertial, viscous and capillary stresses. Theoretical predictions near the point of breakup suggest the emergence of a finite-time singularity, leading to universal power laws describing the breakup, characterised by a universal prefactor. Recent stability analyses indicate that, due to the presence of complex eigenvalues, achieving similarity may only be possible through time-damped oscillations, making it unclear when and how self-similar regimes are reached for both visco-inertial and viscous regimes. In this paper, we combine experiments with unprecedented spatio-temporal resolution and highly resolved numerical simulations to investigate the evolution of the liquid free surface during the pinching of a viscous capillary bridge. We experimentally show for the first time that, for viscous fluids the approach to the self-similar solution is composed of a large overshoot of the instantaneous shrinking speed before the system converges to the nonlinear pinch-off similarity solution. In the visco-inertial case, the convergence to the stable solution is oscillatory, whereas in the viscous case, the approach to singularity is monotonic. While our experimental and numerical results are in good agreement in the viscous regime, systematic differences emerge in the visco-inertial regime, potentially because of effects such as polymer polydispersity, which are not incorporated into our numerical model.