25. Pete Sampras' hair makes us sad.
When: Circa 2000 - Present
In the '90s, Sampras and his full head of Grecian locks dominated the sport. Then, even though Sampras' level of play continued to be at or near the top of the game in the eary 2000s, his hair game was on the fast decline. Young men across the country had to watch their greatest nightmare play out in the national spotlight.