Possible Clues:

• Woeful sound
• Brokenhearted sound
• So sad second letter by the sound of it
• Weep heavily, wail
• Revealing Julie Andrews film
• Initially, the cry of the son of 27 across
• 1981 Julie Andrews movie
• This might make 'er cry, even when she's not been drinking
• A wee ping to get to 'er without a drink too many
• Comics interjection