Drue Wagner at GQ called for a portrait of satire novelist Christopher Buckley. I didn't know much about him at, but you'd hope he'd have a sense of humor with a dad like William F--! I used the pen to reference his well regarded book (and movie) Thank You For Smoking.
A month later Drue called and they wanted a portrait of Russell Simmons. He had just written a book about hip-hop and his Macchiavellian approach to power-building. I thought we should draw him as Macchiavelli and we finalized the above drawing. Soon afterwards Drue let me know the story was being held for the next issue and expanded. A few weeks later we got the story, a humor piece and it referenced 50 Cent and a lot more bling - so this is the one that ran.