Skateboarding was at the outer fringe of popular culture at the time Yeah Right was made, so it felt more like a novel to hear a celebrity talk about skateboarding and use the lingo.
By the time Pretty Sweet came out (nearly 10 years later), skateboarding moved a little closer to the center, so it wasn't as weird to see celebrities inside the skateboarding circle. We had already seen Pharrell, Dave Chappelle, and Tyler the Creator talk about skateboarding.