The paleotopographic history of the North American Cordilleran orogen holds the key to understanding mechanisms of orogenesis and subsequent orogenic collapse. It has been suggested that the orogenic front in western Montana (USA) and Alberta (Canada) was more than 4 km high during Late Cretaceous−early Eocene contractional deformation and during the initial phase of extension in the middle Eocene; however, the late Eocene−Oligocene topographic evolution during continued extensional collapse remains poorly constrained. Here we extend the paleotopographic record in the Kishenehn Basin in northwestern Montana and southeastern British Columbia (Canada) to the late Oligocene by studying δ18O values of fossil mollusks and cement and paleosol carbonates. The molluscan taxa changed from three sympatric groups with preferred habitats ranging from tropical wet, semi-arid subtropical, and temperate during the middle and late Eocene, to mainly a single group associated with temperate environment during the Oligocene, reflecting a decline in molluscan biodiversity induced by climate cooling across the Eocene−Oligocene transition. Reconstructed δ18O values of alpine snowmelt and basinal precipitation decreased by 1.4‰ and 3.8‰, respectively, from the middle to late Eocene, reflecting climate cooling and ∼1 km surface uplift of the basin floor. The reconstructed alpine snowmelt δ18O values then increased by 2.9‰ in the Oligocene suggesting a ∼0.5 km drop in elevation of the orogenic front. Collectively, the results of our new and previously published δ18O data chronicle the paleotopographic response to the change from flat-slab subduction to slab rollback over a 45 m.y. period. These data suggest that the orogenic front was characterized by high elevation (>4 km) in the ancestral Lewis-Clark-Livingston ranges during latest Cretaceous−early Eocene (ca. 75−52 Ma) contraction. The initial phase of extension related to the Kishenehn Basin created a lowland basin with a surface elevation of only ∼1.5 km during the early middle Eocene (ca. 46−44 Ma) whereas the ranges remained >4 km high. The high range elevations were sustained for at least 12 m.y. in the middle to late Eocene concurrent with extension, while the basin floor elevation was uplifted to ∼2.5 km by the latest Eocene (ca. 36−34 Ma). Basin aggradation can explain at most half of the 1 km basin floor uplift. The remaining amount (at least 0.5 km) and sustained high range elevation suggest that range denudation and crustal extension was compensated by the isostatic and thermal effects of slab rollback and/or passage of a slab window and infusion of hot asthenosphere beneath the continent. The range elevation in the orogenic front decreased ∼0.5 km by the late Oligocene (ca. 28 Ma), associated with a decrease in rock uplift rate associated with extension. A post-Oligocene elevation drop of ∼1 km resulted in both the ranges and basin floor reaching modern topography in the Kishenehn Basin drainage, likely due to the regional effect of Neogene Basin and Range extension. This study, along with the previous investigation of the Kishenehn Basin by Fan et al. (2017), are the first studies that systematically investigate paleorelief of the orogenic belt by reconstructing paleoelevations of the mountains and the basin at the same time. The results highlight that the Cordilleran orogenic front of northern Montana and southern British Columbia sustained its high elevation edifice for at least 12 m.y. after the start of extension. We suggest that initial crustal extension did not result in orogenic demise because of concurrent thermal and isostatic uplift.