Bob Iger, Jeff Bewkes, Rupert Murdoch and 7 Other Media CEOs Rated

The media business is so chaotic that a smart move today becomes the monkey on a CEO's back tomorrow—look at MySpace! Peter Lauria rates 10 CEOs navigating these choppy waters.

Who is the most tech-savvy CEO in the media business? Judging by last week’s fawning coverage of Disney’s hiring of Yahoo’s Jimmy Pitaro, it has to be Bob Iger, right? Kara Swisher of tech blog AllThingsD wrote that the Disney CEO “has been one of the old-media moguls who seems unafraid of the challenges of new media,” adding that, “while appropriately wary, Iger acted early and often in exploring digital initiatives at Disney that others in Hollywood’s and New York’s media worlds were loath to consider.” For the famously feisty tech scribe, that’s practically gushing. But before we go giving Iger a star on Sand Hill Road, let’s remember one thing: the expensive failure of Mobile ESPN, which Disney sunk $150 million into developing only to scrap it seven months after launch.

Iger has made some very smart moves, don’t get us wrong, but the plain fact is that every media CEO is still trying to navigate the digital transition. In character and action, they are all still surviving as old-media CEOs who are trying not to dismantle their legacy businesses while dabbling in new media. And every one of them has made some smart and some not-so-smart digital moves. If TV Everywhere catches on, then Time Warner CEO Jeff Bewkes, who has been the chief advocate for the service, which would make cable programming available online once consumers are authenticated as paying cable subscribers, will look like a digital genius, having found a way to preserve the revenue stream from cable TV while also delivering exactly what consumers want—ubiquitous access to content.

Technological disruption of the media business is moving at such a rapid pace that what looks like a smart move today becomes the monkey on a CEO’s back tomorrow. News Corp. CEO Rupert Murdoch looked like a smart young turk when he bought MySpace for $580 million five years ago, so much so that the man he beat to the deal, Viacom CEO Tom Freston, got unceremoniously ousted by Viacom Chairman Sumner Redstone for dragging his feet. Today, however, Rupert’s the dummy, the possessor of a social network whose leadership position was squandered in a phenomenal collapse rivaled only by that of AOL.

NBC Universal CEO Jeff Zucker uttered perhaps the only truism about the digital transformation of media when he rightly noted that media companies can’t trade “analog dollars for digital pennies.” It has been less than two years since Zucker first made that remark and a lot has changed, including the fact that he’s out of a job. Yet Sony CEO Howard Stringer, who has had technological circles run around him by Apple, Nintendo, and others, remains firmly entrenched atop what is viewed by many as an impotent electronics giant.

As these examples illustrate, savviness is relative. We compiled a totally unscientific and subjective list of the smart and not-so-smart digital moves made by the CEOs of 10 of the most important media and entertainment companies and rated their performance. Click through our gallery to see who rates as savvy, somewhat savvy, and not savvy at all. And feel free to let us know what you think in the comments section as well.

Gallery: Tech Savvy CEOs

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Peter Lauria is senior correspondent covering business, media, and entertainment for The Daily Beast. He previously covered music, movies, television, cable, radio, and corporate media as a business reporter for The New York Post. His work has also appeared in Avenue, Blender, and Media Magazine, and he's appeared on CNBC, Bloomberg, BBC Radio, and Reuters TV.