Possible Clues:

• Deposit ending in woe - financial failure all round
• Highest social position - or sliding furniture box
• Drunkard retains pull, being socially superior
• The best artist from the upper classes?
• People of the highest standing reject two prizes
• Upper-class orphan perhaps brought up in lush environment
• Upper class and most popular at the box office
• Two money prizes put up of the highest quality
• People of the highest standing, such as da Vinci?
• Two prizes lifted - that's high-class