I've drawn Edgar Allen Poe 9 times in my career (not including the complete works for Barnes and Noble) and I haven't done him right yet. He's got one of those faces rich with distinct and fascinating features, but I've found that it all comes down to the eyes—the saddest, deepest eyes in literature. Virginia Woolf is a distant second.
He was the first major poet to have a fairly well chronicled photo record and that seems to have made him an archetype for future poets. He doesn't look too affluent, has pain written on his face, and he topped it all off an early and tragic death. The more you read Poe, the more you can read into his face. On the surface, his are scary stories, but the deeper you look into them the sadder they become. Same with Poe's eyes. Maybe I'll get it right next time.