Best (in fact, only) Louis Sullivan building - 2007
Though he didn't invent the skyscraper (that fine distinction belongs to Major William Le Baron Jenney, whose nine-story, steel-framed Home Insurance Building was erected in Chicago in 1885), burly, arrogant, and supremely gifted architect Louis H. Sullivan was the genius behind some of the world's most important early high-rises: the Auditorium Building (1886–90) and the Schlesinger & Meyer Department Store (1899–1904) in Chicago, and St. Louis's matchless Wainwright Building (1891). In his seminal 1896 essay, "The Tall Office Building Artistically Considered," Sullivan lustily proclaims that such a structure "must be every inch a proud and soaring thing, rising in sheer exultation" without a single dissenting line disturbing its majestic columnar structure. But lest you think the master's words prefigure the dreary dogma of stark, unadorned modernism, gaze upon the exquisite, otherworldly Bayard Building (65 Bleecker Street at Crosby). After a tussle with the dull-witted Department of Buildings, construction began in 1897 on what would become one of Sullivan's most beautiful and beloved works, its 165-foot façade clad in a sheath of buff terra cotta wrought into fantastical organic forms that pulse across its emphatic vertical geometry, its superlative cornice a frozen orgasm of graceful foliation. It's almost like being in love—so long as your idea of love embraces piers and spandrels, lunettes, and writhing masses of ornamental effusion.