Let's start with Things My Girlfriend and I Have Argued About. Sweet Jebus is that a long page! I think the author, Mil Millington, is funny as hell. If you like his page, you can sign up for his free mailing list and get an occasional email as well.
Next up: music. Jonathan Coulton sings some really funny stuff. My favorites are his gentle ode to his new computer, A Laptop Like You, and his history of a major furniture store, IKEA.
Jim's Big Ego is another funny band. No free downloads from them, but you can stream all of their songs from their site.
Finally, there's always They Might Be Giants, who you've all probably heard about, but are still funny after 20+ years. You can stream songs from their site, or sign up for their mailing list and get updates and free mp3's occasionally.
