1. Very nice intro song. It's a shame a lot of people would probably skip over it considering where it plays. For me, when I think racing game with catchy, memorable title themes, my mind goes to Re-Volt's:
https://www.youtube.com/watch?v=9tCMImYsCnE - Believe it or not, this was something I thought of back when I was making my own pick, but in light of your choice for #3, I feel the need to post about it~
2. DKC2 is one of my favourite SNES OSTs and David Wise is one of my favourite composers. Love them. Naturally then, I like the song you picked~ For DKC2, my favourite is Mining Melancholy, but... I've actually played the game, so I wouldn't be able to use for this category. Instead, I'll link the snow theme I really like from DKC Tropical Freeze:
https://www.youtube.com/watch?v=sdBpGPyGv40 - Quite a different take, focusing more on the intensity of climbing a snowy mountain rather than the beauty of winter as in DKC2's.
3. It's one of my favourite racing games from my childhood! Last year actually I rediscovered it via RVGL and still play it off and on to this day. Love to chat about this game. In terms of its music, my favourite is actually WestVolt (the song that plays in Ghost Town 1 & 2), but I enjoy basically every song, this one included. As for 1999 itself, a certain other racing game was also released that year with one of game's most iconic intro songs (which I also happen to love):
https://www.youtube.com/watch?v=kQMlzcbfz0I