Possible Clues:

• Everlast "You got me ___ edge"
• Experimental to the point of risk
• Words before town or job
• '___ Good Ship Lollipop'
• and 23: ... two more that may appear before three in 16 using line
• Where and when and how Whitman watched a mother sing a husky song? (2,3,5,2,5,5)
• With 7-Down, feeling better
• Bruce Hornsby "___ Western Skyline"
• __ Q.T. (secretly)
• With 29-Across, like many sales reps