Who

A consummate dealmaker and media industry legend, Diller oversees IAC, the media conglomerate that controls HSN, Ticketmaster, Match.com, Citysearch, and Ask.com, among other properties. His (platonic) wife is fashion designer Diane von Furstenberg.

Backstory

Diller was raised in Beverly Hills—his dad ran a construction company—and he enrolled at UCLA after high school, dropping out after four months to take a job in the mailroom of the William Morris Agency. (Danny Thomas, the father of his pal Marlo Thomas, helped him land the job.) Three years later he became a fully-fledged agent, but he soon left for ABC's programming department, where he made his biggest contribution to the medium by inventing the Movie of the Week. Diller was 32 when he departed ABC to take up the post of chairman of Paramount Pictures, and on his watch the studio turned out a series of huge hits like Saturday Night Fever, Grease, Raiders of the Lost Ark, and Beverly Hills Cop. When Paramount changed hands and Diller clashed with the new owner, Marvin Davis (who famously once called Diller "overrated and overpaid"), he jumped ship, moving over to Fox a year before Rupert Murdoch acquired the company in 1985.

Diller proceeded to do at Fox what many thought was impossible: He carved out a fourth major network to compete with the Big Three, thanks to his embrace of lower-cost reality programming (Cops, America's Most Wanted) and primetime animation (The Simpsons). Mission accomplished, Diller left Fox in 1992 and surprised his glam pals in Hollywood with his next move: taking over the cheesy cubic zirconium purveyor QVC, with financing from cable king John Malone. Running a shopping channel wasn't Diller's end-goal, naturally—it was part of a larger plan to conquer Hollywood, and he quickly made a bid to acquire his old studio, Paramount. He ended up losing out to Viacom and soon departed the shopping channel.

But another mammoth media deal awaited. In a frenzied stretch of dealmaking in the mid-1990s, he cobbled together yet another entertainment/retail empire with such assets as HSN and Ticketmaster, pulling off his greatest coup by acquiring USA Network and the Sci-Fi channel from Edgar Bronfman for $4.1 billion and then selling the entire lot back to Bronfman's partner, Vivendi Universal, several years later in a deal worth $11.6 billion. He's since focused his attention on the several dozen Internet properties in his IAC portfolio.

Of note

For the past few years, Diller's blandly-named holding company, IAC/InterActive Corp. has been home to 60 companies, including Match.com, Citysearch, Ticketmaster, Ask.com, LendingTree, Evite, and HSN. But his hodgepodge approach, which resulted in dozens of disconnected properties existing under the same corporate umbrella—a sharp contrast from, say, Google or Yahoo—was never a structure that earned much favor with investors, nor were many of them too pleased to watch many of the companies in the IAC family struggle to keep up with their peers.

With IAC's stock lagging and with shareholders increasingly unhappy—particularly John Malone, whose Liberty Media controls a 24 percent stake in IAC —in late 2007 Diller announced that he planned to split the company into five publicly-traded companies. His plan wasn't without controversy. Dismayed that the deal would leave him with less control as the company's biggest shareholder, an outraged Malone took Diller to court to try and block the deal. Malone's legal efforts were quashed by a judge in March 2008; in August 2008, IAC was officially divided into five separate companies: retail (HSN); finance (LendingTree); ticketing (Ticketmaster); travel (CondoDirect, VacationSource.com); and IAC proper, a core group of IAC properties consisting of Ask.com, Bloglines, Citysearch, Evite, and Match.com, among others.

Keeping score

Diller was worth an estimated $1.4 billion in 2008, according to Forbes. He earned $295 million in salary and stock the year before, making him the third highest paid CEO in America.

On the job

Diller may be viewed one of the smartest and savviest men in the media business, but he's one of the toughest and most ruthless, too. Notorious for humiliating underperforming execs in front of their peers, he's been known to hurl objects across the room (which likely explains why so many former Diller protégés have moved on). These days his inner circle includes Victor Kaufman, his longtime consigliore; Thomas J. McInerney, his CFO; Shana Fisher, who heads up strategy; and former USA exec Michael Jackson, who heads up the company's programming unit. But all of IAC's employees got a nice gift from up above in 2007 when Diller moved IAC from Midtown to a gleaming new building in Chelsea designed by Frank Gehry.

Namedrop

Herb Allen has advised Diller on numerous transactions over the years and is also his neighbor at the Carlyle. Herb Wachtell and Marty Lipton have served as his lawyers on many occasions over the years. Edgar Bronfman sits on IAC's board, as does Steve Rattner; Marie-Josée Kravis, the wife of Henry Kravis, used to be a board member, but stepped down in 2005. Diller is on the board of trustees of NYU along with John Sexton, Larry Fink, Don Marron, Bill Rudin, Arthur Carter, Ken Langone, and Michael Steinhardt. He developed the IAC building in partnership with Marshall Rose (and also has supported Josh David's plan to redevelop the nearby High Line). Diller has backed several ventures founded by Steve Brill. He's now financing a new media venture by Tina Brown. He's mentored dozens of big shots in the entertainment business, including his two most famous protégés, Jeffrey Katzenberg, who once worked as Diller's assistant, and Michael Eisner, who Diller first hired at ABC. Scott Greenstein used to collect a Diller paycheck. Kurt Andersen still does. Ken Auletta wrote a famously fawning profile of him in the New Yorker; Michael Wolff penned a typically jealous takedown in New York. His closest friends for more than three decades—all fellow members of the velvet mafia—include Calvin Klein, David Geffen, and Sandy Gallin.

Personal

Diller has had a series of boyfriends over his life, including, at one point, the editor-in-chief of the gay magazine The Advocate. He's never officially come out of the closet, though, and things took a surprising turn when he married designer Diane von Furstenberg in 2001. The best of friends for more than 30 years, Diller has been a father figure to her kids since they were young—and the marriage, friends explained, was a reflection of their longstanding friendship. Diller divides his time between LA (where he owns a five-acre home off Coldwater Canyon) and New York, where he keeps an apartment at the Carlyle Hotel. His neighbors in the building include Herb Allen and Tom Ford.

Toys

Diller shuttles between coasts aboard a Bombardier Global XRS, the same $45 million plane that Oprah and Steven Spielberg own. He also owns the 304-foot-long EOS, one of the most expensive sailing ships in the world, which reportedly cost him $200 million.