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It was not until age forty that Lee decided to pursue a career as an artist; she enrolled in Loop Junior College and completed her undergraduate work at Mundelein College in Chicago. After eight years of night classes while working at Northwestern Railroad as a clerk in the engineering department, Lee earned her M.A. degree in interdisciplinary arts education from Loyola University. Lee’s railroad job inspired one of her most popular paintings, Blue Monday, which depicts a woman struggling to pull herself out of bed on a Monday morning. Her trademarks are the animated emotion of the personalities in the artwork and the faces which are painted without features. At age fifty, Lee had her first gallery show; she allowed prints to be made of four of her original paintings. Using her unique designs, Lee also developed figurines, high fashion dolls, decorative housewares, and kitchen tiles.

After showing her work in other galleries for a number of years, Lee opened Annie Lee and Friends Gallery where she displayed her works as well as the works of other artists. When several of her paintings appeared on the sets of popular television shows such as The Cosby Show and A Different World, the exposure helped popularize her work. Although she regularly received requests for public appearances, Lee preferred to appear at gallery shows; she also enjoyed visiting schools to encourage and inspire students.

She passed away on November 14, 2014, at the age of 79.