I had never been on the internet until I moved to Atlanta 10 years ago. My roommate let me use his computer to surf the net. I stumbled upon Tom Richmond's website. Honestly, I had never heard of him, but his artwork was amazing. He's a freelance cartoon illustrator and does a lot of stuff for Mad Magazine. I remember he had a "Me Gallery" which is a collection of all the caricatures that people have done of him. He's since expanded the website and even blogs on a consistent basis about what he's working on, industry stuff, gadgets, etc. It's a must read every day.
Anyway, I finally, finally got the guts to take a stab at his caricature.