“UCLA Sinfest” was printed in a student newspaper from 1991-1994, was very political in an “edgy dudebro liberal” way, and sometimes mocked neo-Nazis and religious fundamentalists.
“Classic Sinfest” was silly fun, though it had some subtly problematic views on women and a few blatantly racist strips (which he later apologized for). It lasted 11 years, from 2000 to 2011. At that point, the Sisterhood was introduced, “Feminist Sinfest” kicked in, yet it still had some problematic views on women.
During the 15 years since then, he’s fallen down multiple rabbit holes, a new one every 2-3 years. Each time there’s been a strip where he went mask-off, but there were not-so-subtle hints where he might be going next a few months in advance. It also took him awhile to “let go” of some of his former beliefs and/or fully embrace his new ones, so even after the mask-off moments it took at least a few more months to fully embrace his new “era”.
His “I love Hitler” moment was in May 2024: https://fstdt.com/DSTF.GJHH2B79 . Though it took several months after that for him to fully embrace his apparent new identity as a transracial White neo-Nazi Odin worshiper. Next up: who knows? There hasn’t been any hints of a new direction yet.