Possible Clues:

• Old Italian painter
• "The School of Athens" painter
• Archangel playing a harp well, having lost wings!
• Painter needs to chat girl up
• Crack empty nut - the famous one associated with the Renaissance
• Italian artist
• Painter's painter bound to flip about height
• Archangel — Italian painter d. 1520
• One who designed many a madonna and archangel
• Artist needing help, a troubled painter