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Artist Gladys Nilsson was born in 1940 in Chicago. Growing up on the city's North Side, Nilsson's artistic interests developed through extracurricular drawing classes during her time at Lake View High School and she went on to study at the School of the Art Institute of Chicago, where she met her future husband, Jim Nutt. In 1964, Nilsson and Nutt helped to found the Hairy Who group, embarking on a series of groundbreaking exhibitions that left an indelible mark on Chicago's art scene. Besides Nilsson and Nutt, the other founding members of the Hairy Who were Karl Wirsum, Jim Falconer, Art Green, and Suellen Rocca.

Through unconventional displays, featuring vibrant and graphic works, the Hairy Who reshaped Chicago's artistic landscape, earning them national and international acclaim. Nilsson's contributions were characterized by playfully mischievous figurative tableaus that reflected her sense of humor and insatiable curiosity. While dynamic and exuberant, Nilsson's work is highly detailed and meticulous. She is prolific in a variety of media, including painting and collage, but she is best known for her colorful watercolors. Her most common subjects are whimsically rendered, elongated figures, which often fill the entire composition. Drawing upon a range of influences, Nilsson incorporates elements of ancient Egyptian tomb murals, Italian Renaissance painting, German Expressionism, and Cubism. Nilsson was also profoundly influenced by her mentor at the School of the Art Institute of Chicago, Whitney Halstead.

Notably, Nilsson became the first artist to secure first prize in consecutive years at the Art Institute's Annual Exhibition by Artists of Chicago and Vicinity in 1967 and 1968. Phyllis Kind began representing both Gladys Nilsson and Jim Nutt in 1969 and, in 1973, Nilsson became one of the first ever female artists to have a solo exhibition at the Whitney Museum of American Art in New York City. As Nilsson's career progressed, she began to experiment with watercolors on paper and collage, incorporating imagery from fashion magazines to explore ideals of feminine beauty.

Beyond Nilsson's contributions as a Hairy Who artist, she has been a longtime supporter of the Art Institute of Chicago, playing a pivotal role as a teacher and advocate in shaping the contemporary art scene. Her works grace major museums globally, including the Art Institute of Chicago, the Museum of Contemporary Art in Chicago, the Whitney Museum of American Art in New York City, and the Yale University Art Gallery in New Haven, Connecticut.