Possible Clues:

• 'Milk' Oscar winner Penn
• With 62-Across, subject of 'Beautiful Boy (Darling Boy)'
• Connery of Bond films
• Penn or Combs
• "House" actor Robert __ Leonard
• Reggae/dancehall artist ___ Paul
• Connery of the cinema
• Roger's predecessor as 007
• Roger's 007 predecessor
• British rapper Jay ___