So I'm going to list a few of the references I randomly thought of while working on my 2nd project.

How failure can be a good thing!

"The Oasis Video That Never Happened" Dir Spike Jonze 1997. It's a short about how Spike Jonze's idea for Oasis' single "Stand By Me" did not happen, also revealing a bit about the process he goes through to make things.

Aesthetics & Music

Nagi Noda
Noda Nagi had a surreal quality about her work that I think works on several levels... a bit meta, but also gorgeously executed.
"Far From Home" music video 2005, artist: Tiga, Dir Noda Nagi
"Sentimental Journey" music video 2003, artist: Yuki. Dir Noda Nagi

Art Movies

"Mark Paints," dir. Spike Jonze. A rarity featuring artist Mark Gonzales finishing a painting only to have a kid come along and deface it.

Beautiful Losers dir. Aaron Rose 2008. This doc is about outsider artists and their rise to fame. A bit of a love letter to the past, celebrating the community and the work that they created.

Artists

Barnstormers, an artist collective famous for time lapse video recordings of the group paintings murals.

Jeremy Blake, a video artist and painter who died last year. Really beautiful work.