Chamberlain did a lot of things really well. But shooting free throws wasn't one of them. For his career, he shot just 51 percent from the charity stripe. Despite this, he steadfastly refused to try to shoot free throws underhand because he didn't like the way that it made him look. His excuse was similar to the one that Shaquille O'Neal used later when he also struggled to make free throws.
"I felt silly," Chamberlain wrote in his book, Wilt. "Like a sissy."