most of the webcomics i've ever been interested in are from the early to mid 00s.
the first one i ever got
really into was
questionable content, which has been ongoing since 2003. i discovered it around 2016/2017 myself, and though it has been a very long time since i caught up with it, it still holds a special place in my heart. it's slice-of-lifey, and in later comics robots become a large part of the cast. very queer.
i discovered
el goonish shive around the same time. it's from 2002. it's... hard to explain, but i love it.
unshelved is another great one about what it's like working in a library. it is also from 2002.
finally,
cheap thrills is a fantastic webcomic about teens in a nowhere town. from 2006. one of my favourites, but if you're really not a big fan of the furry artstyle, it's been rebooted as
rigsby, wi in recent years, and the characters are humans. if you don't mind the furry art, i would recommend reading cheap thrills and then reading rigsby, wi, because the author sprinkles bits of easter eggs in for previous readers.
as i said, most of these are from the early 00s, so keep in mind that they may feature some content or language that makes you cringe or side-eye in 2026, lol.