While technically not advertising, the Lovejoy Columns held iconic paintings that are a part of the Pearl District's past. Trainman Tom Stefopoulos created the paintings between 1948 and 1952 on the pillars of the old Lovejoy ramp that once elevated Lovejoy Street from the Broadway Bridge to NW 14th Avenue.
The ramp was demolished in 1999 but the painted columns were removed and saved. Two are on display in the courtyard on NW 10th between Everett and Flanders. Read more about the columns from James M. Harrison and also see my Drugstore Cowboy posting which featured the columns.
I took these photos in 1999 just before demolition and in 2007 from the exact same spots, on NW Lovejoy between 11th and 12th. The area has changed considerably, to say the least. In an interesting side story, you'll notice that in my 1999 images, the Lovejoy Ramp is still intact and the Kearney Plaza Apartment building construction is well underway, but in the Harrison photos, the ramp is gone and the apartments are not yet built. That's because in August of 1999, the apartment building, when 90% complete, burned to the ground. My photos show the original building while the Harrison photos show the apartment site cleared of rubble and before being rebuilt.