Obviously, the dream CEO for Yahoo is News Corp. President and COO Peter Chernin.

And, no surprise, he is the No. 1 choice of most inside and outside Yahoo in the wake of the news late yesterday that its current CEO and Co-Founder Jerry Yang is stepping down.

Well, Yahoo would certainly be a challenge for Chernin, in terms of a corporate cleanup challenge, especially compared to figuring out how to make bank on plush toys from “The Simpsons.”

But there are many other contenders for the job, despite the slog it could be. Here’s BoomTown’s list…

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Former Facebook exec Owen Van Natta will take the CEO job at a music discovery site called Playlist, a move that had been speculated last week, after he did not end up taking another position as head of MySpace Music.

Van Natta’s arrival at Playlist was not the only news for the Palo Alto, Calif.-based start-up–former AOL exec Bob Pittman’s Pilot Investment Group is also investing an undisclosed amount of money in Playlist, and Pittman will join its board.

The site, which has been called Project Playlist, had previously raised several million dollars. The new round of funding super-sized that, sources said, hovering at about $18 million.

“Discovery around music is exploding on the Internet,” said Van Natta to BoomTown, in an interview this afternoon, giving it as his main reason for joining Playlist.

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Another week, another nonpick for the still-outstanding position to lead Microsoft’s digital business.

Microsoft CEO Steve Ballmer has cast about for more than three months, both internally and externally, for the person who will turbocharge Microsoft’s Web efforts, but no one has emerged a favorite.

Nonetheless, new prospects include former Cisco exec and current Joost CEO Mike Volpi, sources said.

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Longtime Microsoft exec Yusuf Mehdi is taking over a big part of Microsoft’s online services portfolio–including marketing, business development and product management for MSN and the search properties.

But Microsoft has yet to name an overall digital head for these online properties, which has been promised by Microsoft CEO Steve Ballmer since the departure of Kevin Johnson in late July.

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Time waits for no man–but Microsoft CEO Steve Ballmer seems to be taking an awful lot of it in picking who will head the software giant’s long-foundering digital efforts.

Two months after the departure of former top exec Kevin Johnson, most inside the company had expected Ballmer to make the most obvious internal choice of SVP Brian McAndrews. Longtime digital SVP Yusuf Medhi has been seen as the No. 2 candidate.

But many sources report that Ballmer remains more intent on hiring someone outside the company, with the idea that such a person could better re-energize Microsoft’s moribund Internet efforts and bring in a fresher perspective.

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There will be a lot of different reactions to the first of Microsoft’s newest series of commercials, featuring Founder Bill Gates playing straight man to comic Jerry Seinfeld.

Set up as a discount shoe-buying skit, Seinfeld helps Gates purchase a pair called “The Conquistador,” and for some Seinfeldesque reason, it’s churros all around in this marketing effort.

What might be more effective, of course, at least in the Internet arena, is for Microsoft to get off the stick and lay out its next Web strategy clearly, especially in the wake of its failed attempt to acquire Yahoo, and name the digital chief it said it planned to.

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We’re posting all the interviews from the sixth D: All Things Digital conference that took place in late May.

Here’s Part 3 of 4 of an interview Walt Mossberg did with the Gates Foundation’s Melinda Gates.

In this video, Melinda Gates talks about the best ways to fix the broken parts of the public high school educational system in the U.S.

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One thing is absolutely true: It is Microsoft CEO Steve Ballmer and only Ballmer who knows for sure whom he is most interested in to take over the dicey job of head of the software giant’s long-suffering online services business.

But there is a movement afoot among its developers and other execs at Microsoft to push for Chief Software Architect Ray Ozzie, who replaced Founder Bill Gates in the job just over two years ago.

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BoomTown was all busy trying to think of execs to replace Yahoo CEO Jerry Yang, as pressure mounts on him to right the troubled Internet company.

But now, Yang’s position feels safer than ever and it’s his nemesis–Microsoft–that needs a new leader for its long-stumbling online services business.

Microsoft is already been cracking, according to sources, with a wish list of internal and external candidates that CEO Steve Ballmer is now considering.

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Who in the Internet sector hasn’t enjoyed the always amusing stylings of Mr. Ross Levinsohn, the high-profile former head of Fox Interactive Media a.k.a. “The Guy Who Bought MySpace for News Corp.”?
Today, he added another song to his silky smooth repertoire as the “Internet guy who dissed Yahoo.”
In a nice scoop, TechCrunch reported that Levinsohn [...]

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Well, I can tell you what Microsoft might do if it ever got Yahoo to stop snubbing its efforts to acquire the troubled Internet portal.

According to numerous sources familiar with Microsoft’s thinking whom I have been talking to this past week, quite a lot–from creating a single search index to forming one common ad platform to running the place with longtime Microsoft execs at the helm.

So let’s just ignore for now the latest wrinkle in this obviously dysfunctional relationship between Yahoo and Microsoft–which is beginning to remind me of that bizarre Charlie Brown, Lucy Van Pelt and football situation.

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I stopped into the iMeme: The Thinkers of Tech conference, put on by Fortune magazine yesterday and today in San Francisco, and ran into a passel of the Internet regulars, talking about–you guessed it–the Internet.
You got your John Chambers of Cisco, you got your Sheryl Sandberg of Google, you got your Marc Benioff of Salesforce.com, [...]

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