TV boss in a long career since Vaudeville' value $400 answer Greece round Double Jeopardy! Show_number 3091 category ODDS air_date 1998-01-26 question 'After singing for his \maneuver\' value $1200 answer (John) Osborne round Jeopardy! Show_number 3609 category THE JEOPARDY! SWIMSUIT CALENDAR air_date 1984-11-29 question 'He's the 20th century' value $400 answer officer round Double Jeopardy! Show_number 4497 category DRAGONS air_date 2003-02-24 question '16 ounces' value $400 answer Mountain round Double Jeopardy! Show_number 3630 category ANATOMY air_date 1986-11-13 question '9 out.