I used to have Skate, on the wii.
I'd frustrate myself taking on loads of challenges that I'd just make up, and then trying to perfect them, to make them look super awesome.
For example, there was a bit with a vertically wavy pavement, with a ledge next to it, wavy in the same way.
So my aim was to roll up the first wave, flip into a grind on to the ledge, grind down the first wave and up the second wave, and flip out to roll down the second wave.
It took me ages, and I sincerely doubt I had fun, but finally nailing it was awesome.
Seriously, there should be features on a skating game that lets you make a challenge, record yourself completing it, and send it to your friends to attempt.