Barry Diller

Age: 65

Board Afflilations: Coca-Cola Company (KO), The Washington Post Company - Shares B (WPO), Expedia, Incorporated (EXPE)

WHAT HE DOES
Barry Diller heads InterActiveCorp (IAC), a New York holding company that primarily deals in e-commerce websites.

WHAT HE’S KNOWN FOR
Diller can take some of the credit for catapulting Bart Simpson to fame. Or more specifically, for launching Fox Broadcasting, home of the groundbreaking TV hit The Simpsons, during his tenure as C.E.O. and chairman of Fox from 1984 to 1992.

His Hollywood rise was meteoric and unprecedented. In his twenties he became a television programming executive for ABC, and at 32 (in 1974) he was named president and C.E.O. of Paramount Pictures, where he remained until he joined Fox.

After leaving Fox, Diller battled Viacom chairman Sumner Redstone for ownership of Paramount Communications in 1993, but he was outbid. Diller’s brashness, tenacity, and daring secured his spot as a celebrity C.E.O. and visionary and made him a regular among Hollywood’s big names.

Above all, he is a deft dealmaker. In one of his best (and luckiest) deals yet, he purchased the television assets of Universal Studios in 1998 from Edgar Bronfman Jr. for $4.1 billion and then sold them to Vivendi Universal in 2001 for $11.7 billion.

Such shrewdness has inspired other investors to follow Diller’s lead in their own dealmaking, and Wall Street and others to hold out hope that he will produce another astoundingly successful business—something he has yet to do since his days at Fox.

Diller’s occasional attempts to become an entertainment czar have been confusing or tepid—or both. After Fox, he bought a stake in and then became C.E.O. of the home-shopping network QVC (from which he resigned in 1995, after failing to acquire Paramount). He briefly owned USA Networks and now oversees the Home Shopping Network and a stable of decidedly unsexy internet properties, including Shoebuy.com, RealEstate.com, and Gifts.com, at IAC. Though it has been more than two decades since he ran a Hollywood studio, Diller is perceived to be on a quest to regain movie-industry moguldom.

In true showbiz style, Diller is said to be a demanding boss with a taste for life’s finer things. In 2001, Time magazine reported the lore that once, infuriated with Fox executive Stephen Chao, Diller hurled a videocassette at him, leaving a dent in the wall. Diller may think twice about throwing things inside his new IAC headquarters in Manhattan’s trendy Chelsea neighborhood: The building is being designed by renowned architect Frank Gehry.

Diller pays himself nicely too: He earned a total compensation package of $295 million in 2005, which placed him at the top of the list of America’s highest-earning executives. (That distinction prompted New York Times columnist Nicholas Kristof to pen a column about Diller titled “America’s Laziest Man?”)

Though he married fashion designer Diane von Furstenberg, a longtime pal, in 2001, Diller has been dogged throughout his career by rumors that he is gay—and, as such, a possible member of the elite, mysterious “velvet mafia,” a much-whispered-about (and likely unreal) group of influential men in Hollywood who are, or who are believed to be, gay.

WHERE HE’S FROM
Diller was born in San Francisco in 1942 and was raised just a stone’s throw from Hollywood, in Beverly Hills. He attended U.C.L.A. before dropping out to join the mailroom staff at talent agency William Morris in 1961.

WHERE HE’S GOING
With his experience in the entertainment industry, Diller, now living in New York, is continually on the shortlist for top Hollywood jobs. He was rumored to be a favorite for the Disney chairmanship when Michael Eisner stepped down in 2005, but Diller continues to insist that he’s not interested in returning to Hollywood.

For now, his internet businesses are doing well enough. Although his companies often trade at low multiples of earnings—price-earnings ratios—compared with peers such as Google, eBay, and Yahoo, they deliver predictable and solid returns (and generate far less income). But Diller’s reputation for success keeps investors hopeful that this tastemaker will solve his internet puzzle and deliver a smash hit. —Laura Rich