I managed to beat him with Jean-Luc Picard on the first round (he ended up guessing James Watson), but in the second round he nailed it.
I failed with Gordon Ramsay and Slender Man.
EDIT 1: Managed to beat him in the first round but lose in the second with Will Wright.
EDIT 2: Failed with Tetsuo Shima, but won in the first round but fail in the second with Michelle Bachmann.
EDIT 3: Going historical, failed with Rameses II, won first round but lost second with Cao Cao.
EDIT 4: Getting better! Won first AND second rounds, lost the third with the ancient Roman dictator Sulla.
EDIT 5: Finally beat him with King Henry VI of England!