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Loop lessons from Wilson loops in N=4 supersymmetric Yang-Mills theory

N=4 supersymmetric Yang-Mills theory exhibits a rather surprising duality of Wilson-loop vacuum expectation values and scattering amplitudes. In this paper, we investigate this correspondence at the diagram level. We find that one-loop triangles, one-loop boxes, and two-loop diagonal boxes can be cast as simple one- and two- parametric integrals over a single propagator in configuration space. We observe that the two-loop Wilson-loop "hard-diagram" corresponds to a four-loop hexagon Feynman diagram. Guided by the diagrammatic correspondence of the configuration-space propagator and loop Feynman diagrams, we derive Feynman parameterizations of complicated planar and non-planar Feynman diagrams which simplify their evaluation. For illustration, we compute numerically a four-loop hexagon scalar Feynman diagram.