Rieff is the only child of Susan Sontag. His father, whom Sontag married in her teens and divorced in her 20s, was Philip Rieff, author of The Mind of the Moralist.

Rieff was educated at the Lycée Français de New York and attended Amherst College as a member of the class of 1974, where he studied with Benjamin DeMott. He eventually dropped out and went through a vagabond period, during which he labored for the radical Catholic priest Ivan Illich in Mexico and worked as a cab driver. He finally ended up at Princeton University, where he graduated with an A.B. in 1978, and was a Senior Editor at Farrar, Straus and Giroux from 1978 to 1989, working with such authors as Joseph Brodsky, Elias Canetti, Carlos Fuentes, Alberto Moravia, Les Murray, Philip Roth, Mario Vargas Llosa, and Marguerite Yourcenar.

He is a Senior Fellow at the World Policy Institute at the New School for Social Research, a Fellow at the New York Institute for the Humanities at New York University, a member of the Council on Foreign Relations, a board member of the Arms Division of Human Rights Watch, of the Central Eurasia Project of the Open Society Institute and of Independent Diplomat.

Rieff has expressed strong disapproval of the American policies and actions that both informed and followed the invasion of Iraq [1].