Pretty Sweet is not as awful as people make it out to be. MJ's, CK's, and the AO/BA/Carrol section are very enjoyable to me and the video itself is actually filmed really well. It just suffered greatly from Ty's spastic jump-cut editing style and a LOT of unnecessary filler. Overproduction is another thing, but if the head of your production company is Spike fucking Jonze then it's going to get a more distinguishable production treatment than your average full-length video.
I'll also admit there are some extremely questionable music choices throughout and some people's parts were not good (ex. MikeMo). Other than that, watching Pretty Sweet in 2020 and comparing it to our current long-lens, zoom-in Strobeck era makes the current filming style of today look trite & tacky in comparison. The problem with Pretty Sweet is that it's awful aspects completely overshadow the good, but there are more redeemable qualities in it than people give it credit for. Overall, the video is more average/good than the worst skate video that has ever come out like some people overly exaggerate it to be.