In 1993 he received a Guggenheim Fellowship and in 1998 a National Endowment for the Arts Fellowship. In 1995 he was awarded the Whiting Writers' Award. Cunningham teaches at the Fine Arts Work Center in Provincetown, Massachusetts and in the creative writing MFA program at Brooklyn College.
Although Cunningham is bisexual and has been in monogamous partnership for 18 years, he dislikes being referred to as only a "Gay writers", according to a PlanetOut article because while being gay does greatly influence his work, he feels that it is not (and should not be) his defining characteristic.
Although The Hours established Cunningham as a major force in American writing, his most recent novel, Specimen Days, was not well received by American critics . Cunningham has edited a book of poetry and prose by Walt Whitman, Laws for Creations, and has co-written, with Susan Minot, a screenplay adapted from Minot's novel Evening. He is also a producer for the 2007 film, Evening, which stars Glenn Close, Toni Collette, and Meryl Streep.
For The Hours, Cunningham was awarded the: