Thats My Sonic, a Sonic sprite comic that i loved in middle school so much I bought a tshirt. I'm basically assuming the humor was probelmatic I can't clearly remember, but I do know Brian Beubin/Psyguy the author of it turned out to be one of the internet's most notorious sex pests.
also its odd that I was into this series because I was never really into the sonic games and never had a Sega system? I was just the start of a webcomics phase for me which SPEKAING OF
My favorite webcomic in highschool was called Least I Could Do. A comic thats basically about a gary stu author insert who manages to be both a massive fucking nerd (though doesnt look like one, but all his interests are standard geek fair like Star Wars and LOTR) but absurdly successful at sleeping around with women.
The comic was mysoginistic as fuck looking back. There's an early arc where Rayne, the main character, (CW: CSA)
spoiler
hooks up with a 16 year old
. He didn't know she was 16 BUT when he's taken to court over it the judge lets him off because the girl was in a bar which means it "wasnt fair" or some bullshit. The punchline is that Rayne reacts with "oh so that means I can bang 16 year olds as long as they're in bars" while his lawyer and friends try to shut him up.
That was easily the worst arc but the comic is still very misogynistic and sexualizing of its female characters. The comic is actually still running and seems to have matured with Rayne having a steady GF now but its early days are still up there for anyone to read. Worse yet it very definitly did warp my perception of women.