If there's one board I always wanted, it would have to be the Blind Skateboards, Henry Sanchez "Terminator" from 1992.
The board itself was a slick bottom with a T-800 Endoskeleton drawn by Sean Cliver underneath the slick. A rendition of Arnold Schwarzenegger by Cliver was then silk screened over the top of the slick. As the top graphic wore away, it revealed the T-800 below. Kind of like at the end of T2 when Arnie is all battle damaged.
My older cousin's best friend had one when I was ten. I remember inspecting it in the hallway of my aunt and uncle's house every weekend when we'd go visit. Each week more graphic would have deteriorated. Definitely one board that got better with age.