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A career highlight for director Dino Risi and his star Vittorio Gassman, Il sorpasso isn’t just one of the heights of commedia all’italiana but of all Italian cinema. Jean-Louis Trintignant plays Roberto, a shy law student who meets Bruno (Gassman), a larger-than-life Roman playboy who convinces Roberto to join him on a road trip from Rome to the Tuscan countryside. Their travels teach them about each other and themselves, oscillating between comedy and tragedy with powerful and affecting commentary on the easy life. Long admired in Italy, the film has influenced comedic filmmakers including Alexander Payne and Aziz Ansari. (Radiance Films)