Wolff published his first book of essays, White Kids, in 1979. He was most recently a media critic and columnist for USA Today, Hollywood Reporter, New York Magazine and, before that, Vanity Fair and Newser.
In 1997, he wrote the bestseller Burn Rate, about his early dotcom company Wolff New Media. Seven years later, in 2004 he published Autumn of the Moguls, about the decline of mainstream media that would occur later in the decade. However, he was perhaps best known for his 2009 biography of media mogul Rupert Murdoch, The Man Who Owns the News.
Wolff has won two National Magazine Awards, which recognize excellence in the magazine industry in both print and digital mediums. One of the awards was for a series of columns he wrote from the Middle East at the start of the Iraq War in 2003.