I present to you, the Powers Building in Rochester, NY.
Construction began in 1865 under Daniel William Powers, with the building designed by architect Andrew Jackson Warner and completed in 1870. Following its construction, Powers became obsessed with having the tallest building in the city.
To retain this honor, he repeatedly expanded his masterpiece upward. First, he extended its original mansard roof. Then, in 1881, he added an entirely new mansard roof on top of the first. Apparently, two roofs weren't enough, because in 1888–1889, he added a third mansard roof on top of the second.
Meanwhile, in 1887, the nearby Wilder Building had become the tallest building in Rochester. Not one to accept defeat, Powers responded in 1890 by constructing an enormous five-story tower on top of his already ridiculous collection of mansard roofs.
Sadly for Mr. Powers, St. Michael's Church was also completed in 1890, surpassing his project once again. With further upward expansion no longer practical due to structural limitations, he resorted to adding a tall flagpole.
Gaze upon its tall glory, like a person wearing multiple hats.
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