
In 1809 when he was 21, he traveled to Pittsfield, Massachusetts, where he advertised in the Berkshire Reporter that he was eager to & capable of painting portraits for potential clients.

These early notices are the only ads he is known to have placed in any local newspaper. Phillips declared that he would portray his clients with “perfect shadows and elegantly dressed in the prevailing fashions of the day.” It was a promise that Phillips kept for the next 5 decades. His work changed as the fashion, furnishings, customs, & styles of everyday life in 19th-century America changed over time.
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Scholars speculate that his portraits may have been influenced by the work of Connecticut artist Reuben Moulthrop (1763-1814), who had painted Phillips’ namesake, the Reverend Ammi Ruhamah Robbins, in nearby Norfolk. Phillips seems to have known the work of Massachusetts artist, James Brown (active 1806-1808). An 1808 portrait by Brown appears to have served as the model for an 1811 portrait produced by Phillips.
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His early portraits portray almost awkward, even stiff women with almond-shaped eyes and slightly off-center mouths. The method shows heavy outlining, a few props held in their hands, & simple, plain backgrounds. Over the following decades, most of his clients are holding something in their hands including sprigs of flowers; toys; books & letters; handmade needlework; and fashion accessories such as purses & even umberellas.
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By the mid-1820s, Phillips' sitters are more Romantic following the aesthetic of the period. They are strong women with a delicate beauty clothed in the shimmering, pearly colors typical of the Romantic age. As one decade turned to another, Phillips' 1830s seated women became more realistic image reflecting the ideal Republican mother. They are seated and leaning forward from the waist and their determined faces sit atop long, graceful necks.
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By the 1840s, Phillips had serious competition, less expensive photographic portraits. His portraits after that period reflect the rich, saturated colors of the Victorian years. His portraits are more staged reflecting popular studio photography. His women are more realistically portrayed bringing the life-like aspect of photography to the canvas.
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He worked as an itinerant painter in Connecticut, Massachusetts, & New York over 5 decades painting hundreds of portraits. Between 1811 and 1862, Phillips created at least 600 paintings which are attributed to his hand that still exist.
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