Doesn't involve betting, but i always was a fan of this:
Lieutenant. And how came you to leave your last employ?
Point. Why, sir, it was in this wise. My Lord was the Archbishop of Canterbury, and it was considered that one of my jokes was unsuited to His Grace's family circle. In truth, I ventured to ask a poor riddle, sir — Wherein lay the difference between His Grace and poor Jack Point? His Grace was pleased to give it up, sir. And thereupon I told him that whereas His Grace was paid £10,000 a year for being good, poor Jack Point was good — for nothing. 'Twas but a harmless jest, but it offended His Grace, who whipped me and set me in the stocks for a scurril rogue, and so we parted. I had as lief not take post again with the dignified clergy.