I really like the classic Point&Click adventure games, so I say Woodruff and the Schnibble of Azimuth for first place. The characters are humourous, and nothing goes right with normal logic.
For second place, there's Day of the Tentacle. Another great one, a bit older than Woodruff. The graphics are simple, but good.
Woodruff in the past
Bernard and the ski-mask man