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.
Starting in the early 2000s, Rakoff published three books of essays, "Fraud" (2001), "Don’t Get Too Comfortable" (2005), and "Half Empty" (2010), the last of which was awarded the 2011 Thurber Prize for American Humor. He is perhaps best remembered for his essay “Christmas Freud,” which details his experience pretending to be Sigmund Freud in a window display at Barneys New York during Christmastime.
Rakoff was first diagnosed with cancer at 22, but survived after 18 months of treatment in Toronto. He was surrounded by family at his passing, and Rakoff’s death was announced by his mother, Gina Shochat-Rakoff.