19. 'Blood Diamond' (2006)
Leo and co-star Djimon Hounsou won some acclaim for this well-meaning but turgid political action-drama about an enslaved Mende fisherman who partners with a Rhodesian smuggler (DiCaprio) to return to his family in exchange for a massive diamond. The two actors play well off against one another – with DiCaprio's likable sleazebag contrasting nicely with Hounsou's desperate, stone-faced family man. And while the film did shine a light on the corrupt African diamond trade, it managed to do so in a thoroughly ham-handed, Hollywoodized manner.