My beautiful girlfriend's name is Steph. We have been living together for 10 years. She is a music teacher. Her band is called Grey Skies. I would very much love for you to work your lyrical magic with these very few and ill-defined semi-musical variables as the Guide.
I emailed back asking if he wanted to clarify any of it and he said "no". I asked if he wanted Steph actually in the painting and he said "not necessarily".
This leaves things incredibly open. Obviously, music is a major theme in both of their lives. Leon told me he plays in a Dead Kennedys cover band (really, there is such a thing) called The Suede Denims and gives music lessons. So, it has to be musically inspired.
When visual artists try to express music, usually one of two things happen. Either they make a literal image of a performance or a it is bunch of swirling colors and floating cubes. I didn't care much for either of these options.
I decided to approach this like a game that my wife, Beth, and I used to play when people came over. Everyone would lie flat on their backs and close their eyes. I would drop the needle on one of my many old instrumental albums (it could be anything from Billy Strange "Plays the Hits" to Sun Ra and the Myth Science 2000 Arkestra) and we would let the sounds condense as images in our heads. Then, when ready, each of us would sit up and draw. When the song was over everyone presents what they have. (I guess it's not really a game because there is no winning).
Luckily, Leon provided me with a link to a page where I can stream some songs from Grey Skies. I put on headphones, picked a random song, laid down and closed my eyes. The first image that came was of inch worms limping across a branch. When the lyrics began, the worms and branch became an electrical wire. (It turns out the song I picked was called "Bend in the Wire"). The sky was, of course, grey. A bent wire means trouble, sparks. An airplane is flying by, but is it involved. I drew and used this as my preliminary sketch for the painting.
I painted the electrical mess from life. We have a similar scene outside of our bedroom window (minus the bending and sparks). I decided to edit out the apartment buildings and the YMCA across the alley to make it more sparse and dramatic.
I listened to the songs the whole time I painted and got to really like them.
Here is the link Leon gave me so you can listen for yourself:
Please click on it and try this drawing exercise. If you do, email me an image of what you drew. I'd love to see it!