So Sydney was right on both counts! I figured the visible gums and the striped shirt a la Margot Tennenbaum (sans gator) would make the Sydney pic pretty obvious, but Sarah's pic was a little trickier. I meant to approximate her stylish new haircut, as featured in some recent posts on her blog, but besides the axe I couldn't think of any props to give her that would really give it away -- as you've noticed, drawing people in this simple style doesn't make it exactly easy to figure out who the drawing is supposed to be. (Were I drawing the pic today, I'd probably draw her dressed like Enid, or holding an Enid doll.) I still would've drawn her with the axe, though. See, even now, when I visit Sarah's blog, I parse the URL differently -- such that Sarah Ackerman becomes Sara Hackerman (which I really thought was her name until noting her e-mail address). And with a last name like Hackerman, Lizzie Borden naturally springs to mind (so Mets gets partial credit!), hence the axe. Or I guess a crafty cool computer tech could come to mind too, but I'm always going to make the horror connection first. Yeah, baby.
Thanks to all who offered up their guesses, and an extra special thanks to Ditto Ditto for finally commenting! More drawings of people to come. Someday.
Off to the fucking bookstore now. 🙁