The artist received his BFA in photography and painting from the University of Tennessee, Knoxville, in 2001. After earning his undergraduate degree, Milan became an artist in residence at the Skowhegan School of Painting and Sculpture in Skowhegan, Maine. After receiving an MFA in photography from Yale University in 2004, Milan exhibited in the Frequency exhibition (2005–06) at The Studio Museum in Harlem, which featured thirty-five emerging artists living and working in the United States.

The artist exaggerates the fragmentation and reconfiguration techniques integral to collage work in order to point to the layering of history, identity, and time. Deeply saturated and dynamic, Milan experiments with the scale of his work, as well as the proportions of the depicted figures. His figures are often positioned in nature, and are, at times, familiar. As Milan’s collages often combine found materials with original images—he has included cut-out photographs of works by Diane Arbus, Robert Mapplethorpe, and Charles Hoff.

The artist’s works can be found in the collections of institutions including the Whitney Museum of American Art, New York; the Museum of Modern Art, New York; the San Francisco Museum of Modern Art; and the Art Institute of Chicago. Milan has also held solo exhibitions at several institutions including The Studio Museum in Harlem, New York; Crystal Bridges Museum of Contemporary Art, Bentonville, Arkansas; MoMA PS1, New York; the Bronx Museum of the Arts, New York; and the Institute of Contemporary Art, Philadelphia. Milan’s work was first acquired by the Studio Museum in 2007.