We carry out experimental and numerical studies to investigate the collapse and breakup of finite size, nano- and microscale, liquid metal filaments supported on a substrate. We find the critical dimensions below which filaments do not break up but rather collapse to a single droplet. The transition from collapse to breakup can be described as a competition between two fluid dynamic phenomena: the capillary driven end retraction and the Rayleigh Plateau type instability mechanism that drives the breakup. We focus on the unique spatial and temporal transition region between these two phenomena using patterned metallic thin film strips and pulsed-laser-induced dewetting. The experimental results are compared to an analytical model proposed by Driessen et al. and modified to include substrate interactions. In addition, we report the results of numerical simulations based on a volume-of-fluid method to provide additional insight and highlight the importance of liquid metal resolidification, which reduces inertial effects.