Dissipation is ubiquitous in quantum systems, and its interplay with fluctuations is critical to maintaining quantum coherence. We experimentally investigate the dissipation dynamics in single-walled carbon nanotubes coupled to superconductors. The voltage-current characteristics display gate-tunable hysteresis, with sizes that perfectly correlate with the normal state resistance R-N, indicating the junction undergoes a periodic modulation between the underdamped and overdamped regimes. Surprisingly, when a device's Fermi level is tuned through a local conductance minimum, we observe a gate-controlled transition from superconductinglike to insulatinglike states, with a "critical" R-N value similar to 8-20 k Omega.