16. 'Amistad' (1997)
Even at the time, the drubbing McConaughey got for playing lawyer Roger Sherman Baldwin in Steven Spielberg's historical drama seemed excessive, more a product of the actor's overexposure than a lack of talent. To be sure, he's not entirely confident in the role, but his quiet empathy is never in question, and that matters in a movie about seeing beyond our biases to judge people on their own merits. You wonder if McConaughey wouldn't have been stronger in the part today.