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Phillips was born in Colebrook, Connecticut, on April 24, 1788 to Samuel Phillips (1763-1861), as one of eleven children, beginning a life that spanned the period from George Washington to the American Civill War. While it is unknown whether Phillip was entirely self taught or had interacted or been taught by other artists in the Colebrook, Connecticut area, there were such painters whose work Phillip might have seen growing up. Rueben Moulthrop, Nathaniel Wales, Uriah Brown, and Samuel Broadbent are all artists traced by documents to the area. Their stylistic element of their work can be seen in Phillip’s early paintings. He entered the documentary records as an artist himself in 1809, at age of 21. Phillips lived and worked not in established city centers, but new territories openning up throughout New England and Mid-Atlantic. A letter from the American artist John Vanderlyn to his nephew John Vanderlyn Jr., from Kingston, New York dated September 9, 1825, stated “Were I to begin life again, I should not hesitate to follow this plan, that is to paint portrait cheap and slight, for the mass folks can’t judge of the merit of a well finished picture, I am more and more persuaded of this. Indeed moving about through the country as Phillips did and probably still does, must be an agreeable way of passing one’s time. I saw four of his works at Jacobus Hardenburgh’s the other day painted a year or two ago which seemed to satisfy them.” Such a comment from a well established academic painter such as Vanderlyn position Phillips not as a wandering paddler of Art, but instead as an artist with social and economic importance.