Remote sensing data are most useful if they are available with sufficient precision, accuracy, spatiotemporal and spectral sampling, as well as continuity across decades. The Landsat and Sentinel series, as well other satellites are currently covering significant parts of this observational trade space. It can be expected that growing demands and budget constraints will require new capabilities in orbit that can address as many observables as possible with a single instrument. Recent optical performance improvements of imaging spectrometers make them true alternatives to traditional multispectral imagers. However, they are much more adaptable to a wide range of Earth observation needs due to the combination of continuous high spectral sampling with spatial sampling consistent with previous sensors (e.g., Landsat). Unfortunately, there is a knowledge gap in demonstrating that imaging spectroscopy data can substitute for multi-spectral data while sustaining the long-term record. Thus, the objective of this analysis is to test the hypothesis that imaging spectroscopy data compare radiometrically with multi-spectral data to within 5%. Using a coincident Airborne Visible/Infrared Imaging Spectrometer (AVIRIS) flight with over-passing Operational Land Imager (OLI) data on Landsat 8, we document a procedure for simulating OLI multi-spectral bands from AVIRIS data, evaluate influencing factors on the observed radiance, and assess the difference in top-of-atmosphere radiance as compared to OLI. The procedure for simulating OLI data include spectral convolution, accounting for the minimal atmospheric effects between the two sensors, and spatial resampling. The remaining differences between the simulated and the real OLI data result mainly from differences in sensor calibration, surface bi-directional reflectance, and spatial sampling. The median relative radiometric difference for each band ranges from −8.3% to 0.6%. After bias-correction to minimize potential calibration discrepancies, we find no more than a 1.2% relative difference. This analysis therefore successfully demonstrates that imaging spectrometer data can contribute to Landsat-type or other multi-spectral data records. It also shows that cross-calibration from a spectrometer to a radiometer can be easily performed as a result of the imaging spectrometer high spectral sampling and its ability to recreate multi-spectral response functions.