The two Shakespearean title roles that are represented in this crossword puzzle are Troilus and Timon. Troilus is a character from the play 'Troilus and Cressida' by William Shakespeare, which is set during the Trojan War. Timon is a character from the play 'Timon of Athens' by William Shakespeare, which is set in ancient Greece. Both characters are tragic figures who experience great misfortune.