While there are published reports of varietal differences in competitiveness with weeds, no crop varieties have been specifically developed for tolerance to weed interference. We explored several methods that mechanistically compare potential sources of tomato varietal tolerance to purslane, velvetleaf, and black night-shade: 1) The influence of canopy structure and development was studied with a wide range of crop and weed germplasm with different growth habits. Leaf expansion rate and other morphological characters were used to select crop genotypes for more-detailed study. 2) Replacement series experiments with selected cultivars found that purslane and other species can adapt to avoid competition. The greatest varietal differences in competitiveness were with nightshade species that had a canopy structure similar to tomatoes. 3) Field measurements of canopy development and light interception found that competitive advantage shifted over time as height and leaf area of weeds and crops changed. 4) A systems analysis method, sensitivity analysis, found that changes in plant architecture over time were more important than initial or final crop characteristics in determining competitive outcomes.