I made these portrait posters with a 5’ x 10’ KOMO CNC router I was lucky enough to operate for the University of Cincinnati Rapid Prototyping Center. Instead of a cutting tool, I used a plastic Sharpie holder with a spring inside that keeps the marker pressed against the paper. Someone else made it and left it by the machine. I made a few modifications and left it there for the next person.
I made black and white versions of images in Photoshop, vectored in Illustrator, then used Rhino to turn the black areas into a surface that Powermill could recognize. One Sharpie can draw about 5,000 inches before the line gets too wide or the ink gets dry-looking, so all of them are about 5,000 inches of line besides J Dilla, which uses two passes that meet in the middle. They're all 36” in the smallest dimension, because I had a 36” roll of paper. Go big or go home!