I spotted her sitting on a bench surrounded by lush greenery and colorful flowers outside Cafe Flore in the Castro neighborhood of San Francisco. Initially, I was drawn to the flaming orange hair, the purple velvet pants, and best of all, the glittery sandals. Friends who worked in the area told me she was a transgender homeless woman named Anastasia and although many offered to help her, she'd usually refuse and was known to have a bad temper. Some referred to her as "Tragedy Anne". I only saw her once, but she left such an impression on me that day because she looked like a majestic glowing lion sitting upon a throne in garden painted by Rousseau.

I painted her once and was so inspired, I had to paint her again. Sadly, a few months after I painted her two portraits, I was informed she had died alone on the street. I never got to show Anastasia the portraits I painted, and she'd likely have sassed and cursed at me for even approaching her, but I'm glad I captured the fleeting moment I saw her. RIP Anastasia. Medium: Digital paint.





Moving on to a happier urban tale, this is a guy whose name I forget because he was so charmingly flirtatious when I approached him that I was left blushing and rattled. He can be spotted a mile away on Market street due to his brightly colored magenta hair, his colorful sartorial splendor, and his gold tooth glinting in the sun. He spends hours leaning against store windows, slyly eyeballing the passing ladies while posing with his long cigarette holder. Here's a photo of him flirting with me. Don't be jealous.

I know, I go too far sometimes, but I felt the need to draw him again - this time as a magenta butterfly. Medium: digital paint