800 Boylston Street
Breaking ground in 1959 and completed in April 1965, Boson's first skyscraper was the tallest structure in the world outside of New York City. It was the first skyscraper to appear in the Boston skyline and would dawn the onset of many other tall buildings that have appeared in Boston since. Its iconic box-like shape has been the subject of debate since its completion, with many arguing against the architectural style. Skyscrapers are unique in the sense that they are massive and hence very difficult to replace; one could argue that the 'Pru' will continue to draw criticism and praise for many decades to come.
Graphic created by Sherrinford from the Noun Project used under the Creative Common license.