Possible Clues:

• Song from Sondheim's 'Into the Woods'
• Severe pain, mental or physical
• Unending pain
• Stone showed such pain associated with E
• Past state brought woe
• 'The ___ and the Ecstasy' (biographical novel about Michelangelo)
• "... the __ of defeat"
• It comes with painful defeat
• It hurts
• It's horrible the way 15 across gets to New York initially