I've never been good at picking art subjects, but this failing was never more evident than in my early paintings. After my attempts at high fantasy, I decided to paint portraits of music icons.
The first musician's portrait I tried was of blues legend Robert Johnson (1911–1938). I had first heard Johnson's haunting whine and dexterous guitar playing on records my brother owned. At first, I didn't like his scratchy, mournful recordings, but eventually came around to blues music and started blowing all my money on music by artists like Sonny Boy Williamson, Elmore James, and John Lee Hooker.
There exist two known and authorized photographs of Robert Johnson. One features the bluesman holding his guitar, wearing a dapper suit, and smiling handsomely at the camera. The other shows a less-polished Johnson with a cigarette dangling from his mouth, his powerful left hand pressing down the strings of his guitar. I chose, in my portrait, to recreate the latter photograph. Unfortunately, the painting didn't go well. The likeness was poor and I didn't finish important aspects (like the guitar's frets). I eventually abandoned the picture in frustration.
A year later, I attempted a painting of Jimi Hendrix. Though the portrait wasn't based on a particular image, it wasn't very original, either. Any likeness to the guitar legend was owed entirely to my imitation of his eccentric fashion sense. However, my under-painting, skin tones, and highlights were showing considerable improvement.
Just when I was starting doing some new and interesting things with colors, I threw it all out the window and painted a largely monochromatic picture. I owned a copy of The Band's self titled album and really liked the high contrast, black and white photo on the front cover. In a dazzling display of how unoriginal I could be, I attempted an exact recreation of the picture on my canvas. I made a lot of mistakes, but largely achieved what I'd set out to do. Sadly, I had not aimed particularly high.