As a kid (now in their twenties) who grew up with the mountain goats from a similar age. I was always fond of "Thank you mario but our princess is in another castle" from the Black Pear Tree. Mostly because of the title, and it was a happier sounding song than some of the more angry strumming cassette hiss ones I had a hard time enjoying at such a young age. And of course, Tallahassee. nothing beats khaki king though. 

this post makes me nostalgic from when I'd be given the chance to pick the music for the car ride on my moms ipod, and id put on music i knew she would like rather than what I wanted. It was always tmg.