This may be the oldest song on the list, written in 1934.  It typically comes in right behind “A Christmas Song” as the most covered song each season.   Everyone knows every word, and I always loved it as a kid.  Mostly because for the longest time I did actually know the words “Parson Brown” so we mumbled that or made up my own words .  The mysetery made it interesting.  Plus, its hard to listen to it and not have your mood boosted at least a little bit.   I knew this was the right spot on the list for this particular song, but I had a tough time nailing down the best rendition.  I ultimately went with Bing, because this classic song derserved a classic rendention.

Winter Wonderland – Bing Crosby