I like the idea of inducting three at a time for both this and the Hall of Fame.
I nominate 1-3 Center Plaza on Cambridge St. It's monumentally boring and monotonous. It entombs the beautifully restored Adams Courthouse like the Cask of Amontillado.
I'd also like to nominate the Four Seasons. It's a monolithic, inward-looking, brick landscraper, much like its cousin, the Transportation Building, around the corner. It has a parasitic relationship with the Public Gardens across the street, offering its guests gorgeous views of the park while blighting the vistas of those actually within the park. At street-level, its dining room windows along Boylston are walled off above grade, and separated by planter buffers -- designed to look out, but not in. Its Park Sq. side remains blank and dead, despite the flaccid attempt to spice it up with a recent two-story addition. And to top it all off, its drop-off area on Boylston functions as a parking lot, with as many as a dozen cars parked off the sidewalk at any given time. How they get away with this is a mystery to me. Maybe people are more tolerant of parking lots when they're full of Fiats, Benleys and BMWs.