Suricrasia Online - Weird rationalism-adjacent wrting. If you like unfiction you'll like this.
The Merton Website - My personal favourite reviewer on rateyourmusic. Well not anymore since he got publishing-blocked but he's porting all his stuff to a website. When it's done it'll be magical.
Nicky Case - One of the first people to figure out that the best way to explain how things work is to ensure that the other party is entertained. The Evolution of Trust is a good starting point.
Ozy and Millie - A psuedo-buddhist wolf and a mildly sociopathic fox get into misadventures admist the surreal landscape of 2000s america. My pick for best webcomic of all time.
Homestuck - Some kids play a video game and things go a bit off the rails. One of the most important works in the english language, someday i'll make the 6-hour video essay this thing deserves.
Mountain Time - You're kind of just going to have to figure this one out for yourself.
Swan Boy - The story of some extremely well-adjusted people. One of the few things that consistently makes me laugh.
The Jenkins - Haven't kept up with this one in a while, but for a solid few years this was one of the best xkcd-likes out there.
Shadok/LOVEWEB - A ton of really good animations, also a fun animated video essay series about the internet!
Cybershell - Former Something Awful user (i'm not gonna say "goon" as it has been reclaimed) yells about obscure sega games. Better than it sounds.
Todd In The Shadows - Mysterious hooded demon of the night tries to find the worst/best music in existence.