Landscapes respond to external perturbations over a variety of timescales, including million-year tectonic forcing, millennial to decadal climate fluctuations, and minutes-long high intensity storms or large magnitude earthquakes. In mountainous regions, understanding the role of landslides in driving the hillslope response to these perturbations is paramount for understanding landscape evolution over geologic timescales and hazards over human timescales. Here I analyze the landslide-driven hillslope response over millennial to decadal timescales using a variety of tools and techniques (e.g. tephrochronology, lidar and air photo analysis, field and subsurface investigations, and seismic refraction) in the Waipaoa Basin (New Zealand) and Oregon Coast Range (USA). For the Waipaoa study catchment, pervasive landslides have been sculpting >99% of the hillslopes in response to >50 m of fluvial incision following the shift to a warmer, wetter climate after the Last Glacial Maximum (LGM) (~18 ka). Then, starting in the late 1800s, European settlement resulted in deforestation and conversion of >90% of the landscape to pastureland—spurring a rapid increase in landslide-driven erosion. To quantify the landscape response, I first reconstruct LGM and younger paleosurfaces using tephrochronology and lidar-derived surface roughness to estimate the volume, timing, and distribution of hillslope destabilization. From these reconstructions, I calculate the post-LGM catchment-averaged erosion rate (1.6 mm/yr) and determine that the timing of the initial hillslope adjustment was rapid and occurred by ~10 ka. Second, I quantify the rate and volume of historic hillslope degradation using a 1956-2010 sequence of aerial photographs, lidar, and field reconnaissance to map the spatial extent of active landslides, create a ‘turf index’ based on the extent and style of pastoral ground disruption, correlate that with downslope velocity, and calculate the average annual sediment flux. From the sediment flux, I calculate an erosion rate over the past ~50 years (~20 mm/yr) that is 10x greater than post-LGM. Lastly, in Western Oregon, I confirm that seismic refraction can determine the size (e.g. depth) and failure style of landslides in western Oregon—data needed to incorporate these poorly studied landslides into future landscape evolution or hazard models. This dissertation includes both previously published and unpublished co-authored material.