In an interview in Black Issues Book Review, Pearl Cleage reveals that the idea for What Looks Like Crazy on an Ordinary Day came from her desire to write about a character whose doctor informs her that she is HIV positive. Cleage was amazed at how many people she saw in denial about HIV and AIDS, so she created a character who has no choice but to deal with it. This character, Ava, not only comes to terms with her HIV-positive status, but she also finds a way to recreate and reclaim her life.

What Looks Like Crazy is Cleage's first novel. Known for her plays and essays, Cleage felt that this particular story required the novel form to explore the culture of Idlewild and the psychological workings of her characters. Idlewild is an actual city in Michigan that was established after the Civil War as an African-American community. The city was a thriving resort during the 1950s and 1960s, but then it began to decline in popularity.

Although Cleage began writing What Looks Like Crazy in the third person, she realized that her skills as a playwright would make a first-person point of view a natural choice. She told Black Issues Book Review, "As a playwright, I'm used to writing in dialogue."

When Oprah Winfrey chose the novel as one of her book club selections, sales sharply increased, and Cleage quickly reached a wider audience. In 1998, What Looks Like Crazy stayed on the New York Times bestseller list for almost ten weeks. In 2001, Cleage saw publication of a follow-up novel titled I Wish I Had a Red Dress.

In her first novel, What Looks Like Crazy on an Ordinary Day (1997), Cleage depicts the life of Ava Johnson, a modern African-American woman struggling with her HIV-positive status. When this novel was selected for talk-show host Oprah Winfrey's book club, Cleage reached a wide and diverse audience. The book stayed on the New York Times bestseller list for almost ten weeks in 1998, and Cleage's writing in general attracted a great deal of interest. The success of this novel led to the follow-up, I Wish I Had a Red Dress (2001), which takes up the story of Joyce, a character in What Looks Like Crazy on an Ordinary Day.

Academics, theatergoers, and readers regard Cleage as an important contemporary African-American writer and feminist. In addition to plays and novels, Cleage has written poetry and essays. She has contributed to magazines such as Ms. and Essence, and she is a cofounder and editor of the literary magazine Catalyst. Today, Cleage continues to write from her home in Atlanta. She is considering another follow-up to What Looks Like Crazy on an Ordinary Day that would continue the story of Aretha, one of the young girls in the support group Joyce leads.