Jacob Chabot is one of those artists I see often around the New York area. He does stuff like SpongeBob SquarePants and his creator-owned The Mighty Skullboy Army. The first time I met him, it was at MoCCA Arts Festival in 2007. He did a Pokémon spread for Life Meter, and I asked him for a sketch of the monster I identified with most: Snorlax.
Over time, I wound up hitting up Jacob for whatever I was into at that time, like Death Note, Batman: The Brave And The Bold and South Park. I also read a few of his minicomics, which was all-ages fun.
I also found out that Jacob is a fan of Doctor Who. While I haven't asked him for anything too obscure, he has done four great sketches for me from that show, including three Doctors.
Jacob has always been cool to me, and he puts in a lot of effort into his commissions. I usually brings references with me, and he's game to try whatever I have in mind.