During his teenage years, Hezekiah Baker worked in the orange groves and tomato fields — like others with artistic ambition, but little opportunity. He observed Harold Newton and Alfred Hair along with those they inspired earn or subsidize their livelihoods with art-making. Baker began painting in the late 1960s. He watched as the formation of the Highwaymen went about its business, but since his wife Gladys preferred a spouse who brought home a paycheck every Friday, Baker held traditional jobs: he sold insurance, baked bread at Dandee Bakery, and later ran his own restaurant, House of Foods. But all this time he yearned to paint; so much so that he took a correspondence art course. One day he showed a painting to Alfred Hair and Hair asked him how long it took to make the painting. When Hezekiah replied it required the better part of a day, Hair offered to share with him his own fast painting approach. Then Baker was able to enjoy painting and selling and thereby contribute to the legacy to which all the young artists were contributing.