Howard Heston Bailey (1836 - 1878) was an American calligrapher and artist. Born in Ohio, Bailey began his career as a calligrapher, selling business cards and illustrated advertisements to businesses across the Midwest. At some point in the late 1860s, Bailey met T.M. Fowler (1842 - 1922), who may have been working for Albert Ruger. Bailey and Fowler must have become close friends and Fowler's daughter even asserted that Bailey 'taught her father how to draw' city views. In 1870, Bailey entered the world of view making, publishing nine impressive bird's eye views of places in central and southern Wisconsin, at least one of which was published by Fowler. The following year, another twenty-two city views appeared with his name on them as either the artist or publisher, with Fowler publishing at least eight of them by himself or in partnership with Bailey. 1872 was another productive year for Bailey, who published a view of Milwaukee that year, along with a view of Columbus, Ohio, on which he collaborated with his brother Oakley Hoopes Bailey (1843 - 1947). The publishing firm Fowler and Bailey first appeared in 1872 as well, making it impossible to know exactly who, and in what combination, the two Baileys and Fowler drew and published views bearing that imprint. The trio moved to Ithaca, New York in 1873, and all three men remained busy, drawing and publishing views under various different imprints. In 1874, H. H. Bailey published a view of Poughkeepsie with James Compton Hazen (1852 - 1908), who had been his subscription agent in Syracuse the previous fall. Hazen spent the next four years working with Bailey. Fowler and Bailey went their separate ways in 1875, publishing thereafter under the names H. H. Bailey and Co. or H. H. Bailey and J. C. Hazen. Over the course of his career as a viewmaker, Bailey published seventy-two views, not including those published under the Fowler and Bailey imprint, on which he must have worked. According to John W. Reps, 'No viewmaker surpassed H. H. Bailey in his careful representation of industrial and business districts.'