This Letter reports the first measurement of the $^{235}$U $overline{ u_{e}}$ energy spectrum by PROSPECT, the Precision Reactor Oscillation and Spectrum experiment, operating 7.9m from the 85MW$_{mathrm{th}}$ highly-enriched uranium (HEU) High Flux Isotope Reactor. With a surface-based, segmented detector, PROSPECT has observed 31678$pm$304 (stat.) $overline{ u_{e}}$-induced inverse beta decays (IBD), the largest sample from HEU fission to date, 99% of which are attributed to $^{235}$U. Despite broad agreement, comparison of the Huber $^{235}$U model to the measured spectrum produces a $chi^2/ndf = 51.4/31$, driven primarily by deviations in two localized energy regions. The measured $^{235}$U spectrum shape is consistent with a deviation relative to prediction equal in size to that observed at low-enriched uranium power reactors in the $overline{ u_{e}}$ energy region of 5-7MeV.