Possible Clues:

• Risky proposition
• Certain game option
• "Where Eagles ___"
• "Bet ya can't!" e.g
• Skate on thin ice
• Take a big chance
• Read about stuntman, when tied to 7 Across
• 'You wouldn't --!'
• Challenge some newspaper advertisement that will be taken the wrong way
• "Make my day," e.g.