This statue is called “Allow Me” and was created by J. Seward Johnson. It sits in Pioneer Square near the Max station. Locals simply call it the “Umbrella Man.” As in, “Meet me at 6 by the Umbrella Man.”
It apparently has siblings though, one in Philadelphia on Broad and 15th, and another one in Bath, New York. Cyclotram has a lot more info about him and his siblings, including the artist.
*EDIT* Since I first posted this blog post about J. Seward Johnson’s “Allow me,” I found myself in Philadelphia in February 2012. As I was looping the block trying to find my hotel (Loews Philadelphia, I can highly recommend it,) I spotted this fellow out of the corner of my eye.
Holy Cow! In my excitement I almost took out a Taxi Cab with my SUV rental. Or maybe he was going to take me out anyways, it’s a bit hard to tell with East Coast drivers. I had actually forgotten that this statue was here. On my previous visit to Philadelphia I had only a few hours to look around, but the next day I had plenty of time to wander back around and revisit this statue. Unfortunately it was near impossible to really get a good photo – the theater had a billion people coming and going, and the sidewalks were full. It took me nearly twenty minutes just to get these two pictures.
I ended up having a ton of time to really experience Philadelphia’s art. For the record, since a few of my readers are… um… “challenged,” the top picture is of Portland’s version in Pioneer Square. The bottom two pictures are of Philadelphia’s version, located in front of the Prince Music Theater on Chestnut street between S 15th and S Broad Street. Please no comments calling me an idiot and saying the location is wrong and there is no way that statue is there. 
