Got Vinyl?

So I've noticed a trend out here in blog land.
Vinyl.
Vinyl letters cut with Cricut machines.
It occurred to me, I have both items.
In fact, I have the original Cricut and my mom has both the original and the Expressions.
I have vinyl.
TONS of vinyl.
Why won't mine work?
Here's my vinyl:

Here's more vinyl:

Here, I'll show you what I'm doing, maybe you can help.
I'll choose this one:

I know my Cricut works, and I know this is Quality Vinyl, why won't it fit?

I even went down the street (yes, my mom and dad live two blocks down), to see if it would work in the Expressions.
I got this:

Am I doing something wrong?

Hehe!

~nic