Randall is the first African American woman to co-write (with Matraca Berg) a number one country hit. Over 20 of her songs have been recorded, including several top ten and top forty records; her songs have been performed by Trisha Yearwood and Mark O'Connor.

Randall is also a novelist, whose first novel The Wind Done Gone is a reinterpretation and parody of Gone with the Wind. The Wind Done Gone is essentially the same story as Gone with the Wind, only told from the viewpoint of Scarlett O'Hara's half-sister Cynara, a mulatto slave on Scarlett's plantation. The estate of Margaret Mitchell sue Randall and her publishing company, Houghton Mifflin, on the grounds that The Wind Done Gone was too similar to Gone with the Wind, thus infringing its copyright. The lawsuit was eventually settled, allowing The Wind Done Gone to be published. The novel became a New York Times bestseller.

Randall's second novel, Pushkin and the Queen of Spades, was named as one of The Washington Post's "Best fiction of 2004."

Randall received the Free Spirit Award in 2001 and the Literature Award of Excellence from the Memphis Black Writers Conference in 2002. She was a finalist for an NAACP Image Award in 2002.