So here are a list of my current favorite webcomics:
Daily Dilbert- I really enjoy the comic. It has been long-running and updates daily. His blog about politics and technology is also interesting (although the actual politics behind it is take-it-or-leave-it as long as you can separate an interesting read from having to agree to everything).
Saturday Morning Breakfast Cereal- It also updates every day or two. Quite funny with different takes on things. Not every joke is a hit but there is funny alt-text and a red post-script joke button at the bottom.
Penny Arcade- A comic about gaming, mainly. Some of the comics are quite niche for whether you have followed the news stories or not, but it tends to be okay. I thought their earlier works were better.
Cyanide and Happiness- A dark webcomic with off-kilter humor. However, it is more main-stream dark humor so no danger of it going over people’s heads.
Awkward Zombie- Another gaming webcomic. They don’t update as much as the others (tending to be once or twice a week), but the comics are always funny. Once again, limited enjoyment if you don’t know anything about the games being parodied, though.