Scott the Engineer agreeing to let Lexington Steele fuck him in the ass at Giants Stadium on Pay-Per-View for $250,000.
It's my favorite because he agreed to it without thinking it through, and then had to back out because he found out that he humiliated his son who was still in high school at the time.
Scott is such a money hungry and selfish bastard and its great. Go back to the push up challenge for some great radio. His block party shenanigans were great too.