A failed entrepreneur, former New York columnist, and the author of several books, these days Wolff pens a media column for Vanity Fair.

A New Jersey native and Vassar grad, Wolff started his working life as a copy boy at the Times before moving on to write for Esquire and the New Times. He published his first book, White Kids, in 1979. Then came a slew of ill-fated media projects: He tried to take over the National Lampoon, attempted to launch a travel magazine, and spent the middle part of the 1990s trying to get Wolff New Media off the ground. Like his previous projects, though, the venture never panned out and it was shuttered in 1997 amid controversy. But Wolff managed to turn the experience into a book, 1999's Burn Rate, a gossipy account of his company's demise. In 1999, Wolff was tapped by former New York editor Caroline Miller to serve as a media columnist for the mag. Another bid for mogul status followed when he attempted take over New York after it was put up for sale by Primedia in 2003, but Bruce Wasserstein snatched the mag away from the consortium at the last minute. Wolf landed at Graydon Carter's Vanity Fair shortly thereafter.

It's a touch ironic that a man who never managed to achieve any success in the business world spends his days critiquing and second-guessing people who, for the most part, have succeeded. But while Wolff may be a doomed businessman, his observations about the media business are often spot on—assuming, that is, that you can get through his exceedingly self-indulgent writing. Unfortunately, the lesson Wolf should have learned during the past three decades—that he's better off typing at a keyboard than running a business—has yet to sink in. In 2007, he launched Newser.com, an online content aggregator. Ironically, Wolff ripped his own business model to shreds in the pages of New York several years ago: "I have seen this business plan many times—numerous entrepreneurs believe that the market demands a way to regulate the anarchy of content. We need a global editor (editor-in-chief of the world) to tell us what information we can trust." Who knows, perhaps the 6th time will be the charm.

Wolff is estranged from his wife, Alison Anthoine, a fellow Vassar grad and a lawyer. They have three children. The marriage crumbled after it was revealed that Wolff was having an affair with a former Vanity Fair intern named Victoria Floethe. [Image via Getty]