One of the most interesting series ever is Closer To Truth, which "presents the world's greatest thinkers exploring humanity's deepest questions." For instance: is mathematics invented or discovered?
Of course, it's not necessarily an either/or question. In addition to Stephen Wolfram, the show also posed the question to other prominent thinkers, including Steven Weinberg:
And Roger Penrose:
Check out their YouTube channel for tons of other fascinating discussions.