The Picasso of Jazz was apparently also a fan of Picasso himself too, so much that he also wanted to paint himself! Jokes beside, his search for artistic expression was not enough that he is one of the most celebrated and creative musicians of all-time, he also sought his love of painting in the last period of his life. Even the fact that him seeking more shows why he was this successful and special, along with his love of celebrating life as it is.
"It’s like therapy for me, and keeps my mind occupied with something positive when I’m not playing music” he once said, reminding us to not forget to enjoy life while losing ourselves in the greedy success and fame cycle. Although it is a common thing for successful musicians to feel attraction to other art forms, the thing that sets Miles Davis apart is his absolute search to get better and his interactions with the art community-as he was a very social and a challenging person that he allowed other people crush his ego time to time.
He collaborated with artists such as Joni Mitchell and Jo Gelbard (which later became his art teacher and girlfriend), but the first interaction was tenser than one would expect. Gelbard, who was a lifetime friend for Davis, would recall these meetings with fright and love: “I was scared to death! I could barely speak.”
Contrary to his moody and minimalistic soft music (generally), the artwork he created was full of neo-expressional screams influenced by artists Joni Mitchell, Picasso, Kandinsky, Jean-Michel Basquiat, and African tribal art. He was representing the feelings and ideas that he was not able to or didn't intend to reflect on his music. It is certainly interesting that he still had those ideas after years of never-ending creative processes that ended up with him making at least 51 studio albums.