A consummate dealmaker and media industry legend, Diller is the chairman of 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.
Diller was raised in Beverly Hills and dropped out of UCLA after four months to take a job in the mailroom of the William Morris Agency. 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, 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. Diller's next move was the blandly-named holding company, IAC/InterActive Corp. has been home to 60 companies, including Match.com, Citysearch, Ticketmaster, Ask.com, LendingTree, Evite, and HSN. After streamlining his hodgepodge holdings in 2008, Diller stepped down as CEO in 2010, but still act as chairman and senior executive.
On a personal note, 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. 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. [Image via Getty]