For me, the craziest prop bet in recent memory was a $2M weight loss bet Ted Forrest won in ~2010 to go from 188 to 138 lbs in 2 months. It's been almost a decade so some of the most dramatic pics are hard to find but here's one of the ones I found: http://www.flushdraw.net/wp-content/uploads/2014/09/forrest-...