Rakoff was known for his humours essays and his association with American writer David Sedaris and THE AMERICAN LIFE host and producer Ira Glass. He began his career in publishing at HarperCollins before becoming a regular contributor to the New York Times Magazine, GQ, Conde Nast Traveler, and Outside Magazine.
Rakoff was also involved in theatre, first, directing a play written by Sedaris and his sister Amy Sedaris, and later acting in plays. He also appeared in movies The Watermelon Woman, Capote, and Strangers with Candy, and on television shows COSBY and SNAKE‘N’ BACON. He played modeling agent Rich Tuchman in AS THE WORLD TURNS in April 1998.