"Outsider Art" was selected by Harold Bloom for "The Best of the Best American Poetry 1988–1997". Since 2006, Ryan has served as one of fourteen Chancellors of The Academy of American Poets. On January 22, 2011, Ryan was listed as a finalist for a 2011 National Book Critics Circle Award. On April 18, 2011, she won the annual Pulitzer Prize for Poetry, calling her collection "The Best of It: New and Selected Poems" (Grove Press) "a body of work spanning 45 years, witty, rebellious and yet tender, a treasure trove of an iconoclastic and joyful mind."