3. Billy Crystal
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."