My cousin Jeff is a trumpet player.
He asked me to do a caricature of him holding his pride and joy: a 1950 Bach Trumpet. I was also asked to include the Stegosaurus tail under the table. Apparently he and his kid are big into dinosaurs.
What separates this from the other caricatures I've done is that it's a physical painting. Instead of doing the color in Photoshop and sending him a digital file, he wanted the actual painting. Normally I'd do this on illustration board, but frankly, I'd procrastinated too long and wanted to give him something more, so I did it on canvas.
I drew the elements in pencil, scanned them in and built the scene in Photoshop (his head and body were drawn on separate pieces of paper). Then I printed that out, transferred the image to canvas using graphite carbon paper and drew the outlines in fine point Sharpie, which won't run or bleed when paint is applied. Then I painted the image in acrylics, layering the color to give them some vibrancy. When all was done, I then went back and redrew most of the line work in Micron art pen, which is cleaner and a scooch darker than the Sharpie.