I'm not sure if a comic has ever made me cry, but as a lad I always thought Man-Thing #5, "Night of the Laughing Dead," about the clown who commits suicide was pretty sad.
Re: Jimmy Corrigan. Those were always bleak and I remain an admirer of Chris Ware, but as Acme Novelty progressed, it just got more and more downbeat. The humor than ran through the earlier issues seemed to dissipate in later years. I didn’t even read the last one; I got tired of feeling beaten over the head.
Currently I find Seth very emotionally engaging. His work has as much depth and insight as a lengthy novel.