I played Jude, the rebel angel kid who'd been hanging around on earth in Manhattan since the early twentieth century. I pictured him and the rest of his gang wearing a variety of pieces of anachronistic clothing, topped off by Brooklyn Dodgers caps (the session was set in Hell's Kitchen in the '70s).
Jesse's Jack Lemmonesque-devil incarnate salesman was a lot of fun. One part sad sack and two parts SOB. I totally pictured The Smiling Man as being played by the actor who played "The Mayor" on Buffy the Vampire Slayer, but even creepier.
I've enjoyed playing IAWA and it was nice to take it for a spin using one of the Oracles that wasn't Sword-and-Sorcery inspired (Demon City Blues), but I'm about ready to try something else.