Superboy #160

Few images in 1969 DC comics carry this much emotional weight: Neal Adams renders a guilt-wracked Superboy on his knees in space, head buried in his hands, with Earth looming large behind him as he cries out that no punishment is bad enough — he must exile himself from family, friends, and his home planet forever. The title "I Chose Eternal Exile!" promises a story built around genuine anguish rather than action-for-its-own-sake, with interior work by the creative team of Frank Robbins, Bob Brown, Wally Wood, and Ray Holloway. It's a striking, introspective cover that captures the teenage hero at what looks like his lowest moment.