I distinctly remember the first time I encountered the comedic stylings of Adam Carolla. My friend Carlton and I were doing homework together at his house, and he had MTV's "LoveLine" on. I had never seen it before and wasn't paying much attention at first, but he kept distracting me by making me laugh from his wiseass remarks and eventually I just put my books aside and enjoyed the show. Since that show, I've seen or heard Carolla for probably hundreds of hours on television, radio, film, and now his podcast with partners-in-crime "Bald Bryan" Bishop and Teresa Strasser. For the drawing I kept the style a little less cartoony than normal and colored the scanned drawings in Photoshop. I used the smudge tool to help soften up the rough graphite lines and help smooth out the tone variations in the skin.
9/19 update: I did another pass on this picture to punch it up a bit, added a text border with all the in-jokes I could fit, then printed out some copies and gave them to the Ace Man himself when I saw him over the weekend at a live show in North Hollywood. Here's the new version:
Here's a shot of the two of us after the show (I wore my Red Dead shirt because I wanted to speak with him about the game (He's mentioned it every so often over the last few months on his podcast: