Greco's "The Way Out" definitely fucked me up when it came out. Right when the Cocteau Twins song hit I was just like fuckkkkkkk.
I got sober a few months before he did (still clean) and the way he portrays the misery of addiction as well as loneliness of sobriety but through the lens of skating as a coping mechanism was very heavy and honest to me.
To me it was a very sincere and genuine piece of art from one of skating most superficially inconsistent figures, so it was refreshing to see something like that from him.
Not to mention the skating was truly fucking incredible and the soundtrack was perfect.
Reynolds in Stay Gold, like others have said, is a good one...
Absolutely Jason Dill in Photosynthesis...walking down those stairs mid-line...are you fucking kidding me? Insane.
Definitely not tear-worthy, but just a beautiful part in a skate video: Greg Hunt's part in Tincan Folklore when it cuts to the tortoise song and its 8mm footage of a homeless man playing guitar, then cuts into to Greg's impeccable skating. So great.
Dylan's parts wont ever be the same...damn.
There's a lot, skating is an art form, and good art is provocative.