Cooling was born in Chester, Pennsylvania. She was educated at Pratt Institute (B. F. A., 1973) and the Art School of the Art Institute of Chicago (M. F. A., 1975).

Cooling began her career in the late 1970s and early 1980s exhibiting lesbian erotic paintings: portraits of lovers, self-portraits with her lover, and double portraits of gay and lesbian couples. This work is lyrical, evocative, intimate, and explicit. Cooling abandoned her erotic work in 1986 because of difficulties in exhibiting the paintings.

The sheer joy of sensuality continues to infuse her work, however, which is distinguished by the vibrant and visceral use of color and a complex interplay of abstraction and realism.

In the mid-1990s, as a tenured professor in the Fine Art Department at San Diego State University, Cooling returned to her roots and again began painting works with overtly lesbian erotic content. The lesbian content in these new paintings is presented in an even stronger and more powerfully sophisticated way than was the case in the earlier work.

On the basis of her powerful series, the Paintings from Hell's Kitchen, Cooling was awarded the highly coveted Marie Walsh Foundation Space Grant for 1998.

Cooling's mature work continues to bring her recognition as a major contemporary painter and bridges lesbian art further with the mainstream. Never one to shy away from radical territory, she has chosen to be a pioneering trailblazer, a lesbian artist inventing new imagery.

She and her partner of many years, Jackie Corlin, have formed a foundation to collect under-recognized and under-collected women painters, particularly lesbians and women of color, thus creating a legacy on many levels.