[EricH]

I have to say the 2006 season.

To start out, the official hint was:

..........five 'bots tangling with pasta
a game piece obsessed with a shovel's show
.....and seeing Montana's green heights

Dave's "hints" included comments about a fox being in the henhouse and hovercrafts and the English Channel.

"shovel's show" was a reference to "Just Shoot Me", starring David Spade. But a lot of people went after "seeing Montana's green heights" and researched Joe Montana, the state of Montana, and anything related. (Montana was just a placeholder, IIRC. Something had to go between "seeing" and "green heights".) Oh, yeah--some people tried the haiku angle. They hadn't seen the shape.

2007 was pretty good too. Had lots of people playing with photoshop. One even pulled a fake by inserting a banana. The game piece was, however, correctly guessed.