21. Roger Clemens
Clemens played for 24 seasons in MLB for four different teams. Astonishingly, he was an 11-time All-Star and won two World Series in his glittering elite career. He also won seven Cy Young Awards, more than any other pitcher in MLB history. He also made a guest appearance on “The Simpsons.” That’s when a celebrity knows that they have made it.
After turning 40, he continued to have an excellent career. Clemens became an All-Star three more times. He won the last of his Cy Young Awards at the age of 42. There weren’t many better than him at his best. He finally retired in 2007. Unfortunately, a number of scandals have since tainted his reputation.