28. Robert Baratheon
A brash, blustery aristocrat who rises to the top on a wave of popularity but finds out he's much better at winning power than knowing what to do with it? Where have we heard that story before? Such was the life of the late king of Westeros, a Falstaffian figure who clung to his former glory like a high-school football player gone to seed. Eventually, his kingdoms fell apart and even his closest advisors schemed to help speed up his removal from the throne. His victory was his tragedy.