The Holiday season is known for surprises. One of the biggest came in 1977 when, during a broadcast of Bing Crosby's Merrie Olde Christmas television special, a fresh-faced young pitcher named H. Leroy Halladay popped up on screen to sing a duet with the crooner. The contrast was striking: the wholesome, white-haired, White Christmas icon of yesteryear and the face-breaking man in red who dashes the spirits of nine men each start. Despite the odd pairing, it would be an understatement to simply say that it worked. As with everything Roy Halladay touches, it was a masterpiece... and the performance, like all, lives on for generations.