Possible Clues:

• Dramatist
• Dramatist in predicament is unusually wary
• Shakespeare, say: fun, perfect for audience
• 'Wilbur, get in the game!'
• Wilde or Wilder
• Shaw or Pinter, among others
• Will, say, competent musicians do it for an audience?
• Shakespeare was to gamble on women, okay
• Dramatist is wary, possibly put in dangerous situation
• Coward, possibly, with authority to hold up progress of game