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The above jack-o'-lanterns are all connected through one of the faces carved into one of the pumpkins.
One of the conntections between two of them is obvious, the other, not so much. To help with the not-so-much connection, check out this picture here.
(And, yes, sadly, those are the dorky sneakers David wears. His wife is ready for a divorce.)
Once you have the second connection, to advance to Level 2, type into the box the last name of the actor (not pictured) who serves as the missing link.