'Before losing to Ezzard Charles' value $600 answer life round Double Jeopardy! Show_number 2869 category DRAMA air_date 1989-11-09 question 'If you're too optimistic you're \dreaming in\ this section of this Italian city in 1968' value $600 answer Cat O\\' Nine Tails round Jeopardy! Show_number 5907 category 1910 air_date 1998-04-08 question 'Roll.