The pirate and the sherriff are drawn freestyle, the two guys and Roosevelt were drawn loosely from photographs. President Roosevelt I deliberately started with the intention of not attempting a likeness, but instead simply capturing the attitude of his pose. Having failed that, I took pains to make his face look a like the photo so that there was some merit to the excercise. I may or may not have succeeded in that effort so I wrote his name along the bottom of the picture to avoid any confusion.
(When I was a child I made it a habit to provide a label of the things I drew pictures of. If I drew a picture of my father I would write the word, "Dad." If I drew a truck, the word "TRUCK" was written below it. Spider-Man would be clearly described in a word balloon as "Spider-Man." I found this eliminated the awkward moment when an adult was not sure what it was they were looking at. A wrong guess could be painful. "No, Mom! That's not Superman, that's Spider-Man!" Ugh!
Thus: "Theodore" across the bottom of that drawing. So we-- you and I-- do not have one of those awkward, painful moments. (I'm considering making this a regular feature of my artwork.)
Drawn on paper with pencil and pitt pens/brushes, over-texturized and colored hastily in photoshop.