Who: Carter is the bon vivant editor-in-chief of Vanity Fair and pal of countless celebs and moguls. He also serves up mediocre food to the same crowd as the co-owner of the Waverly Inn and Monkey Bar.

BACKSTORY: Edward Graydon Carter doesn't have the pedigree you'd expect from the editor of Vanity Fair. A native of Ottawa and a college dropout, he spent time working on Canada's railway system, stringing wire between telegraph poles in rural Saskatchewan, where he reportedly told his blue-collar co-workers he was Jewish because he thought it would make him seem like more of an intellectual. After returning to Ottawa and working on a small Canadian literary magazine, Carter moved to the city, briefly working as a trainee at Time before setting out on his own as a co-founder of the legendary satirical magazine Spy, along with Kurt Andersen and Tom Phillips.

Spy put Carter on the map, but when the mag's moment in the sun seemed to have passed, in 1991 he abruptly left and accepted the editorship of Arthur Carter's New York Observer. In less than a year, he managed to turn the sleepy community rag into a hotbed of gossip about media and politics. But he didn't remain there for long: In 1992, following Tina Brown's move to The New Yorker, Si Newhouse offered Carter the top job at Vanity Fair. Dismissed by media critics as a nobody when he first arrived at Condé Nast, even Carter himself was convinced his tenure would be short. (He's said he looked up his name in the company directory daily to make sure he was still listed.) Carter settled into the job alright: Fifteen years into his tenure, he's established VF as one of Condé Nast's most valuable franchises and become one of the most powerful-and highest paid-editors in town.

Of note: Carter has turned Vanity Fair into one of Conde's most valuable titles, and along with Vogue it's also one of the company's most profitable. One of only three editors who report directly to Newhouse (the others are Vogue's Anna Wintour and David Remnick of The New Yorker), in recent years Carter has become a power broker extraordinaire, a position he calculatedly uses to his advantage to land stories and covers, not to mention launch lucrative side businesses.

That he's the ultimate insider-look no further than the white-hot post-Oscar party he inaugurated-is more than a little ironic considering he made his name skewering celebs, not cozying up to them. But it fits nicely with his personal transformation from outsider to consummate insider: These days the former railroad worker from Canada cavorts with media moguls and celebs and is clad in bespoke $5,000 Anderson & Sheppard suits, the same sort that are worn by none other than Prince Charles himself. But he doesn't spend all his time sucking up to celebrities. He's also played to his demo by using VF to passionately denounce George Bush and the Republican administration, fury he channeled into his 2004 book What We've Lost.

On the side: Carter has long had various side occupations to keep him busy. Several years ago it was film: He executive produced the documentary 9/11 and the Robert Evans-directed doc The Kid Stays in the Picture, and his mere suggestion to Brian Grazer and Ron Howard that they make A Beautiful Mind earned him a $100,000 thank-you check. (The latter, in particular, earned him the scorn of fellow editors who cried foul at the apparent conflict of interest: "Carter has permanently tainted the fruits of whatever success Vanity Fair has enjoyed during his 12 years as editor and made its motives suspect to its readers," wrote his former employer the Observer.) Burned a bit by the foray into film, perhaps, Graydon has a new hobby these days: the restaurant biz. He co-owns the Waverly Inn with nightlife impresarios Sean MacPherson and Eric Goode, and teamed up with hotelier Jeff Klein and restaurateur Jeremy King to open a second eatery, Monkey Bar, in 2009.

On the job: Carter is one of the highest paid editors at Condé Nast; he's rumored to make more than $2 million a year. (Of course the perks are impossible to quantify.) While Condé Nast pays for a car and driver for Carter, sadly the gig does not come with access to a private jet. Fortunately his mogul pals, like Barry Diller, David Geffen, and Ron Perelman, are more than happy to help out: During the Christmas holidays Perelman regularly gives Carter a lift down to St. Barts aboard one of his two Gulfstreams.

Personal: Carter is married to his third wife, Anna Scott. His first wife was a French-Canadian he married in the early 1980s. His second wife, whom he proposed to at the Empire Diner in Chelsea after knowing her all of three weeks, was a former paralegal named Cynthia Williamson. The couple split after 18 years of marriage, reportedly after Carter admitted to having an affair. They have four children together: Ash, Mike, Bronwyn, and Charles (who goes by "Spike"). Following their divorce in 2000, Carter spent some time playing the field (he was briefly involved with Samantha Boardman) before tying the knot with Scott in Connecticut in 2005. Martin Scorsese, Robert De Niro, Anna Wintour, and Sumner Redstone were among the attendees. In 2008, he and Scott had their first child together, daughter named Isabella Rose.

Carter lives in a Greek Revival townhouse at 22 Bank Street. Built in 1844, the home features six bedrooms, double parlor, sitting room, terrace, and several fireplaces. (Uncle Si helped with the $3 million purchase in 2005, as is customary for the company's top editors.) Prior to that, Carter lived at the Dakota on the Upper West Side. He also has a Colonial style estate in Roxbury, Conn., which he bought for $1.42 million in 2004. Like many of his Hollywood pals, a Prius sits in the driveway.

Vice: Carter, who famously railed against Mayor Bloomberg's smoking ban, claims to have kicked the butts prior to his 2005 nuptials. (At one point, he and Scott engaged the services of a smoking-cessation guru from Ireland, who charged Carter and his wife $2,500 for a private smoking cessation course.) Alas, he's been spotted on numerous occasions since.

[Photos via Getty Images]

Vital Stats

Full Name: Edward Graydon Carter
Date of Birth: 07/14/1949
Place of Birth: Toronto, Canada
Residences: West Village; Roxbury, CT
Filed Under: Media, Publishing