publication date: Thursday, May 27, 1999 (part of Round IV)
clue: Gentlemen such as Miller and DiMaggio prefer blondes.
explanation: One of Monroe's best-known roles was in "Gentlemen Prefer Blondes." Monroe was also famous for marrying (and divorcing) playwright Arthur Miller and baseball player Joe DiMaggio. more…
trivia: Goos that fit into multiple categories (historical and acting), such as Monroe, appeared frequently during this time in the game.