This paper presents a driving skill analysis for comparing different drivers in various operating conditions. The analysis demonstrates how driver model variables, e.g., preview time and transport delay, effect path following and dynamic behaviors of various heavy vehicle combinations. Three types of heavy vehicles are evaluated, i.e., a tractor only, tractor/semitrailer and multi-trailer B-train, in a closed-loop single lane-change maneuver. To assess the driving performance, two measures, i.e., Path Following Score (PFS) and Combined Stability Scores (CSC), are introduced. The result displays driver ability in terms of a visualized spectrum, highlighting the features of driving behavior while driving different types of heavy vehicles.