Here is the saddest drawing I've ever done. I originally sketched this Maddie in October 2006 . Yesterday when I "inked" it in Illustrator it made me really melancholy and it took me to a place where I didn't want to go but then I got stuck there. Maybe because I was also listening to Steely Dan and Bonnie Raitt albums. The drawing feels like "defeat."
The original was part of a more elaborate drawing. I got hung up on perspective  and on trying to turn it into a more literal scene. Last night I put a detail of the second 2006 sketch version behind Maddie in this quick Photoshop workup:
Is Maddie dejected enough on her own or do the real blues come in knowing that through the window people are meeting and smiling and having fun without her?
My original sketch had the window closer with the group members toasting the boss, and Maddie's nemesis giving her a smirky glance out the window. (Pencil sketch, right.)
Below is the original sketch quick-painted in Photshop (also in 2006), in my attempt to analyze and achieve some "noir" lighting.
It is typical of me to miss the expressive potential of my work as I labor over some academic standard of correctness. ("Good girls draw lines with rulers.") I'm reading a book now on post-Impressionist painter Marc Chagall (1887-1985). His colorful paintings told many stories in many scenes but didn't give a hoot about setting up formal perspective.
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 For the "Pandora" project
 influence of my cartooning class
 Maddie copied from Illustrator and pasted into Photoshop as a Smart Object.