April Ludgate
By the end of Parks and Recreation, April Ludgate has made some impressive moves, but her time as an intern was something else. April is dark, cynical, and pretends not to care about anything. Her biggest screw-up was when she accidentally booked all of Ron's meetings for the same day because she didn't believe that March 31 was a real date.
Gilligan
Gilligan's heart was in the right place, but his efforts always went awry. If the rest of the castaways on Gilligan's Island had let the headhunters have him or fed him to the giant tarantula or allowed him to perish in any number of ways, they likely would have been back to civilization in a matter of weeks.
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