I agree, 5 isn't enough. But, here's mine anyway.
These are my most favored 'cause they are tied to special/important/nostalgic memories:
1. These Are Days - 10,000 Maniacs
2. Lightning Crashes - Live
3. Possession - Sarah McLaughlin
4. Caught a Light Sneeze - Tori Amos
5. 6 Underground - Sneaker Pimps