Much has been made of the fact that the drawing of the person on the cover of the "Another Self Portrait" Bootleg collection doesn't look much like Dylan. Some have suggested it might be Tommy Makem, but what if the identity of the person on the cover of Another "Self Portrait" is the obvious choice, Bob?
As an artist, Dylan is more interpretive, he isn't much of a draftsman, his paintings capture a mood or feeling very well, but they don't ever pretend to be strictly realistic. In painting the cover for "Another Self Portrait," did Dylan feel that he'd captured something of himself at that time, even though it doesn't particularly look like him?
Looking at the photo first slideshow photo, above on the left, paired with the cover drawing (click the "View 5 photos" tab to open the slideshow) taken in Woodstock in 1968 by Eugene Landry, (all but Bob's face is cropped out here) we can see that elements of the two faces are very similar. The right eyebrow (on the right, looking at the photo and drawing) is higher in both cases, the left eye in the drawing has a line coming down from it, indicating a similar shadow as on the photo under the left eye. In both cases, the upper lip is thin, the lower lip full. The white turtleneck-ish collar in the drawing roughly approximates the white shirt in the photo. The hair in the drawing is straight and parted, but in '68 Dylan had his hair cut short and sometimes parted it, as is seen in the other slideshow photos. The face of the painting is more straight and angular that Dylan's oval facial structure, but then again, Dylan the draftsman acquiesces to Dylan the artist trying to create a feeling.
The feeling that the painting on "Another Self Portrait" conveys, if you look closely enough, is one that is perfectly represented by the following Dylan lyric - "It’s never been my duty to remake the world at large, nor is it my intention to sound a battle charge." (Wedding Song/Planet Waves) Dylan was far away from the vortex that nearly pulled him down into oblivion, was trying to live a simpler life, if that was at all possible, and the painting on the cover of "Another Self Portrait" precisely captures that.