Billy Crystal, who grew up on Long Island, has been a Yankee fan his whole life.  He is almost always seen sitting in Yankee Stadium,  wearing a Yankees cap.  Crystal directed 61*, the HBO movie about Roger Maris and Mickey Mantle's home run race. 

In March 2008, Crystal got the chance of a lifetime, when he signed a minor league contract with the Yankees, and led off for the Bombers as the DH in a Spring Training game against the Pirates.  Crystal fouled a ball down the first-base line before striking out on six pitches.  Crystal called it the "greatest moment of my life."

Top 10 Famous Fans