Here are three Rorty videos I’ve enjoyed. The first is an intro, with other philosophers opining about him, recorded soon after his death in 2007. The second is a wonderful conversation with philosopher Donald Davidson (in six parts, 65 mins). The third is a wide ranging interview titled, Of Beauty and Consolation (featured below, 67 mins), which struck me as intimate and honest. I am inclined to see Rorty as an American version of a scholarly Tibetan monk in the tradition of Nagarjuna.

Additional reading (more here):
Richard Rorty: What made him a crucial American philosopher?  
Rorty on Bernard Williams: To the Sunlit Uplands
Last words from Richard Rorty