Possible Clues:

• 'O, I am fortune's fool!' crier
• "Wherefore art thou ___?"
• 1961 Petula Clark hit single
• A loving character, this writer, wearing jumper
• "___ + Juliet" (1996 movie)
• Tybalt's dispatcher
• Juliet's loverboy
• Amorist
• Tragic hero with a capital O?
• Shakespearean hero