Landscape complexity promotes ecosystem services and agricultural productivity, and often encompasses aspects of compositional or configurational land cover diversity across space. However, a key agricultural diversification practice, crop rotation, extends crop land cover complexity concurrently across space and time. Long-term experiments suggest that complex crop rotations can facilitate yield increases in major crops. Using a compiled county-annual panel dataset, we examined whether yield benefits of crop rotational complexity were apparent on a landscape scale in the conterminous US for four major crops between 2008-2020. We found that the benefit of rotational complexity was only apparent for cotton and winter wheat, and that the benefit for wheat was driven by one region. Corn exhibited the opposite pattern, wherein higher yields were consistently obtained with lower rotational complexity, while soybean yield appeared relatively insensitive to rotational complexity. Effects of rotational complexity were sometimes influenced by agrochemical usage. Positive effects of rotational complexity were only apparent with high fertilizer for soybean and wheat, and with low fertilizer for cotton. Corn yield in high-complexity, low-yielding counties appeared to improve with high fertilizer inputs. For the overwhelming majority of acres growing these major crops, crop rotation patterns were quite simple, which when combined with the short time span of available data, may explain the apparent discrepancy between long-term experiments and nationwide data. Current demand and incentives that promote highly intensified and specialized agriculture likely hinder realization of the benefits of rotational complexity for production of key crops in the US. Increasing rotational complexity where major crops are grown thus remains an underutilized approach to mitigate landscape simplification and to promote ecosystem services and crop yields.