Brad Garlinghouse’s appointment to a new job at AOL today as its new communications czar is yet another sign of an interesting trend for those keeping score of the comings and goings of top Internet execs.

Garlinghouse came to the Time Warner (TWX) online unit after a year-long break, preceded by six years at Yahoo (YHOO).

As anyone who watches the digital space knows by now, this kind of management musical chairs is common and never-ending.

In fact, borrowing a quote by IAC/InterActiveCorp (IACI) CEO and chairman Barry Diller from an onstage interview I did with him at the sixth D: All Things Digital conference and switching out Hollywood for Silicon Valley: “[It] is a community that’s so inbred, it’s a wonder the children have any teeth.”

But, given all the movement of late, this insider seat-switching seems more frantic than ever, as allegiances shift, competitors become friends and colleagues become rivals faster than you can tweet.

When he left Yahoo last summer, in fact, the digital chatter was that Garlinghouse would take a job either as a venture capitalist (he had been one once) or helming a start-up (that too, at Dialpad.com).

In fact, sources said, Garlinghouse had been considering two mobile gigs, but opted for helping to try to overhaul a troubled Web giant.

Fixing messes was the impetus of Owen Van Natta, who left a top job at social networking giant Facebook in early 2008 and by the end of the year, headed over to run Project Playlist, a controversial online music-sharing service.

But then he had hightailed it by spring to try his hand at reviving MySpace, as its CEO.

His boss, News Corp. (NWS) digital head Jon Miller, did the same, getting the hook (unfairly to my mind) at AOL several years ago and then creating an investment firm with former MySpace head Ross Levinsohn.

The pair considered being part of a bid to oust Yahoo management in 2008.

Miller’s freedom lasted only until he got an offer that he presumably could not refuse from News Corp. head Rupert Murdoch recently. (Full disclosure: News Corp. owns Dow Jones, which owns this site.)

The list goes on, chock full of ex-Yahoos, in fact.

Its one-time COO, Dan Rosensweig, left the company in 2006, for example, and joined the well-known private-equity firm, Quadrangle Group.

But, soon enough, he was scooped up by Activision Blizzard (ATVI) to run its Guitar Hero division.

Yahoo Network head Jeff Weiner also departed from the Internet giant, in mid-2008, for a stint at two VC firms.

He landed at LinkedIn, the business-networking service where he was named CEO in late June.

Greg Coleman ran Yahoo ad sales until mid-2007 before taking a job at AOL earlier this year, which he lost after it got new management soon after.

At Yahoo, Coleman sparked with former advertising sales head Wenda Harris Millard, whom he ousted. She went onto Martha Stewart Living Omnimedia (MSO) and left there this spring for the Media Link consultancy.

Presto! She is now helping MySpace’s Van Natta fix the social networking site’s ad business.

Current Yahoo U.S. advertising head Joanne Bradford actually came from Microsoft last summer, via her own short visit to the troubled ad start-up SpotRunner.

Former Yahoo search techie Qi Lu now runs digital for Microsoft (MSFT), along with a big gang of ex-Yahoo techies he has recruited.

And Scott Moore is even better at the switcheroo. He was at Microsoft running MSN U.S. content, switched to Yahoo as its media poobah, left last year to consider a start-up and then headed back to Microsoft as head of U.S. content this year.

But former Google (GOOG) execs have also been busy shuttling hither and yon, mostly to innovative start-ups.

Of course, many find refuge at Facebook (COO Sheryl Sandberg, PR major domo Elliot Schrage and many more) and Twitter (GC Alexander Macgillivray and COO Dick Costolo).

Recent departures–such as Sukhinder Singh Cassidy, who landed at Accel Partners for now–are also likely to find new homes soon enough.

And, of course, there’s always Garlinghouse’s new boss, former Google ad head Tim Armstrong, who took over at AOL earlier this year.

We’ll skip former Joost CEO and former Cisco (CSCO) exec Mike Volpi (who is now a VC); former Netscape Communications/short-term VC/ex-banker/current-for-now CBS (CBS) digital head Quincy Smith; and Joanna Shields, who has worked at Real Networks (RNWK), Google and Bebo (which was bought by AOL)–for now.

Because, around and around and around it always goes, as you can see in this funny video below, which I posted previously:

[Musical Chair designed by Jacob Mathew.]

New MySpace CEO Owen Van Natta starts his first day on the job at MySpace bright and early this morning, coming to its Beverly Hills HQ as he takes over for co-founder and former CEO Chris DeWolfe.

Along with him will be a new COO, former AOL exec Mike Jones, whose appointment will be announced this morning, sources said.

The pair will meet with MySpace staff today at 3:30 p.m. PDT.

Jones was the founder of Userplane, a social-networking application maker that was bought by then-AOL head Jon Miller in 2006.

Miller is now the digital chief at News Corp. (NWS), which owns MySpace.

(News Corp. also owns Dow Jones, which owns this Web site.)

Jones left the Time Warner (TWX) unit last year to start Tsavo, a digital content start-up.

Van Natta, who was running the Project Playlist start-up until his appointment, has stronger Silicon Valley ties. For now, he will commute to MySpace from Northern California, where his family lives.

Van Natta was a former top-ranking Facebook exec, still holding a small stake in the MySpace rival, and has also worked at Amazon (AMZN).

But, with a strong product and technology background, the Los Angeles-based Jones is an excellent choice to be a partner to Van Natta–who was hired by Miller last week in a flurry of change at the social-networking site.

Their challenges include: Reinvigorating the MySpace brand, upgrading its technology, adding more innovation to its feature set, continuing to grow its nascent advertising business and dealing with the tough renegotiation of its lucrative search and advertising deal with Google (GOOG).

They must also play deft diplomats at MySpace, where many remain loyal to DeWolfe and to co-founder Tom Anderson. Anderson is in talks to step down as president for an unspecified new role in the company. He currently remains president.

See a chat I had with Jones in the video below that I did at a gathering of Beta South, a networking organization for digital start-ups in the Los Angeles area, last year. (Jones is at the start, talking about the differences between Silicon Valley and Southern California.)

And if you want to read an informative and solidly reported piece on Van Natta–and are perplexed as BoomTown is by factually-challenged and agenda-stuffed diatribes of some about him–try out this one in The Wall Street Journal today.

Here is Jones in my video:

Legendary MTV Networks exec and co-founder John Sykes (pictured here in an interview on PBS’s “Charlie Rose” show) will replace Owen Van Natta as CEO of the controversial music-sharing site, Project Playlist.

He is a high-profile choice to take over for Van Natta, who was officially named CEO of MySpace this morning by News Corp. (NWS).

Van Natta, who also worked at Facebook, will remain an adviser to Playlist, which is based in Silicon Valley. It is not clear where Sykes will be located.

Sykes–who is on the Playlist board–was one of the original executives who launched the iconic music-focused cable channel 25 years ago, before leaving last year. He was also a key exec at both VH1 and Infinity Broadcasting.

He is well regarded in the music industry, an important criterion since Playlist has been dealing with legal attacks from some music labels. Settling with them will be key to the start-up’s survival.

Former AOL and MTV exec Bob Pittman, who is an investor in Playlist, worked closely with Sykes at the Viacom (VIA) unit.

FOR IMMEDIATE RELEASE:

Playlist Names Board Member and Veteran Media Executive
John Sykes as CEO

MTV Co-founder and Former VH-1 President Replaces Owen Van Natta

Palo Alto, Calif., April 24, 2009–Playlist, the leading social media network where over 43 million music fans discover, create and share playlists, announced today that Board Member and industry veteran John Sykes has joined the company as Chief Executive Officer. As a Co-founder of MTV, President of VH1, and CEO of Infinity Broadcasting, Sykes brings extensive operating experience and industry relationships to the company as it partners with the music industry to provide advertising, subscription and e-commerce services to music consumers.

Owen Van Natta will serve as an Advisor to Playlist.

“John was a pioneer of the MTV revolution that forever changed the music industry landscape by giving fans a whole new way to discover and enjoy music,” said Bob Zangrillo, Chairman of Playlist. “Playlist looks forward to leveraging John’s tremendous track record operating media businesses and deep relationships in the music industry as it builds out the world’s premier social media service.”

“Creating and sharing playlists has become a phenomenon in our culture. With over 43 million registered users, Playlist is the number one site where fans go to discover, share and enjoy their favorite music,” said John Sykes, CEO of Playlist. “Leveraging our newly forged partnerships with the music community, we can now offer consumers deep access to their music and provide the industry with powerful new revenue streams.”

Playlist, one of the fastest growing sites on the Internet, continues to establish partnerships with the entertainment industry in an effort to offer a comprehensive collection of content that can be discovered, shared and monetized at www.playlist.com.

Former Facebook COO Owen Van Natta has finally been officially named as CEO of MySpace, as BoomTown reported yesterday, according to a press release from News Corp.

He will replace CEO and co-founder Chris DeWolfe, who stepped down from the job earlier this week. DeWolfe will remain a strategic adviser at MySpace.

Van Natta, 39, will take over immediately and be based in Los Angeles, where MySpace has its HQ. But, with strong ties to Silicon Valley, he is likely to give the site more of a high-tech infusion.

Van Natta has most recently been running Project Playlist, a controversial music-sharing start-up based in Palo Alto, Calif. Previous to that, he worked at Amazon (AMZN).

He will be replaced there, in turn, by well-known former MTV Networks exec and co-founder John Sykes.

No other new top execs at the huge social-networking site have been named yet, as some had reported.

Instead, it will be up to Van Natta, who will work closely with and report to new News Corp. digital head Jon Miller, to energize the current staff and recruit new talent to MySpace.

The social-networking giant has seen its buzz and momentum wane in the face of the juggernaut growth of Facebook.

Van Natta played a key role in Facebook’s formation, striking key investment and advertising deals with Microsoft (MSFT), for example. He left after it was clear he was not going to become CEO, a job held by founder Mark Zuckerberg.

Nonetheless, MySpace is still the largest social network in the U.S., although Facebook is close to surpassing its size.

All Things Digital broke the news earlier this week that Van Natta was the top choice of News Corp. (NWS), which owns MySpace.

(News Corp. also owns Dow Jones, which owns this Web site.)

In his new job, Van Natta has a lot of challenges, including: reinvigorating the MySpace brand, upgrading its technology, adding more innovation to its feature set, continuing to grow its nascent advertising business and dealing with the expected end to its lucrative search-advertising deal with Google (GOOG).

He also must play deft diplomat at MySpace, where many remain loyal to DeWolfe and to co-founder Tom Anderson. Anderson is in talks to step down as president for an unspecified new role in the company. He currently remains president.

Here’s the full press release on Van Natta:

News Corporation Names Owen Van Natta Chief Executive Officer of MySpace
______________________

Los Angeles, CA, April 24, 2009–News Corporation today announced the appointment of Owen Van Natta to the role of MySpace Chief Executive Officer effective immediately. Mr. Van Natta will be based in Los Angeles and report directly to Jonathan Miller, News Corporation’s CEO of Digital Media and Chief Digital Officer.

A highly-regarded digital executive, Mr. Van Natta, 39, previously served as Chief Revenue Officer and Vice President of Operations for Facebook, where he helped negotiate Facebook’s $240 million investment from Microsoft. Earlier, he served as Vice President of Worldwide Business and Corporate Development for Amazon.com. Most recently, he was the CEO of Playlist, Inc., an online music company.

“Owen combines a deep understanding of social networking, a keen business sense and the operational experience to guide MySpace through its next phase of growth. I’m confident his leadership will be an invaluable asset,” said Mr. Miller. “I plan to work closely with Owen to shape our long-term vision around this vibrant community that already attracts more than 130 million users worldwide.”

“I’m thrilled to have the privilege to pilot MySpace in what is sure to be an incredibly exciting and rewarding next chapter for the business,” said Mr. Van Natta. “I feel honored to build upon the immeasurable achievements of the MySpace founders and look forward to working with Jon and the MySpace team to meet the challenges and make the most of the opportunities before us.”

While serving as Vice President of Operations and Chief Revenue Officer for Facebook, Van Natta focused on revenue operations, business development, strategic partnerships and technical operations. As Vice President of Worldwide Business and Corporate Development at Amazon.com, he managed global marketing programs and strategic partnerships. He was also part of the founding team of A9.com, the Amazon.com search company, and was responsible for site operations and sponsored-link advertising. Owen earned a B.A. from the University of California at Santa Cruz.

Former Facebook exec Owen Van Natta will be named CEO of MySpace as early as tomorrow said sources close to the situation.

He will replace CEO and co-founder Chris DeWolfe, who stepped down from the job yesterday. DeWolfe will remain a strategic adviser at MySpace.

News Corp. declined comment.

No other top execs at the huge social-networking site will be named yet, as some have reported.

Instead, it will be up to Van Natta, who will work closely with new News Corp. digital head Jon Miller, to energize the current staff and recruit new talent to MySpace, which has seen its buzz and momentum wane in the face of the juggernaut growth of Facebook.

Nonetheless, MySpace is still the largest social network in the U.S., although Facebook is close to surpassing its size.

All Things Digital broke the news yesterday that Van Natta was the top choice of News Corp. (NWS), which owns MySpace.

(News Corp. also owns Dow Jones, which owns this Web site.)

In his new job, Van Natta has a lot of challenges, including: reinvigorating the MySpace brand, upgrading its technology, adding more innovation to its feature set, continuing to grow its nascent advertising business and dealing with the expected end to its lucrative online ad deal with Google (GOOG).

He also must play deft diplomat at MySpace, where many remain loyal to DeWolfe and to co-founder Tom Anderson. Anderson was in talks to step down as president yesterday for an unspecified new role in the company. He currently remains president.

Van Natta knows from tense company politics. He left Facebook last year after serving as its COO, and also as chief revenue officer, after his relationship with founder and CEO Mark Zuckerberg foundered.

But before that, he was key to striking its lucrative search and advertising deal with Microsoft (MSFT) as well as negotiating the $240 million investment by the software giant that valued Facebook at an eye-popping $15 billion.

Van Natta has most recently been running Project Playlist, a controversial music-sharing site.

A purchase of the start-up is not part of this deal, sources said, as it had been in previous talks Van Natta has had with News Corp. about other digital jobs.

Previous to Facebook, Van Natta worked at Amazon (AMZN) in a number of capacities.

Finally, Owen Van Natta is about to win out over a founder.

The former Facebook COO (pictured here) is poised to become the CEO of MySpace, replacing co-founder and current CEO Chris DeWolfe.

DeWolfe will likely get a title as a special adviser to MySpace in a deal that is still coming together.

Settling all the specifics could take at least a day and there is always the possibility that this changing-of-the-guard deal could fall apart. But multiple sources close to the situation said it is more just a matter of ironing out the details.

Thus, the die seems cast for Van Natta to take over the thorny job of rehauling MySpace, which is owned by News Corp. (NWS).

(News Corp. also owns Dow Jones, which owns this Web site).

In a post this morning, MediaMemo was the first to name Van Natta as the only candidate in the running to take over as leader of MySpace.

It’s familiar territory for him.

Van Natta never got the big job at Facebook, which is under the firm control of founder and CEO Mark Zuckerberg.

But Van Natta–who got to Facebook in its early days after stints at various companies, including Amazon (AMZN)–was a key early player in making the social-networking site into the juggernaut it is today.

He played a large role in its advertising and investment deals with Microsoft (MSFT), for example, as well as in hiring many of its current execs.

But, like many at Facebook, Van Natta left Facebook in early 2008 under tense circumstances, although he now is on good terms with Zuckerberg and others at Facebook.

Maybe not any longer.

In a delicious digital irony, he will be taking on Facebook head on, as MySpace–once the momentum player in the space–tries to regain its step against Facebook.

Van Natta is currently CEO of music start-up Project Playlist and it is not yet clear what will happen there. When he was previously talking to MySpace about running its music site, there was speculation that it might buy the start-up.

Today’s developments have happened quickly and without a lot of advance planning.

The talks to complete this deal are being led by new digital boss Jon Miller (pictured here), who came to News Corp. last month.

News Corp. officials declined to comment on the developing situation.

But sources said that Miller hadn’t been planning on getting rid of DeWolfe in the near future, and until yesterday, he was still evaluating his options.

News Corp. CEO Rupert Murdoch had once treated DeWolfe as a favorite and gave him significant autonomy at MySpace.

But Murdoch, who brought Miller on, has been leaning toward a change in leadership as MySpace’s traffic has stagnated and its buzz and momentum have moved to Facebook.

Under DeWolfe, many have felt it has dropped the ball on innovation and in making key improvements to its technology and features.

Worst of all, MySpace’s lucrative $900 million search advertising deal with Google (GOOG) is also coming to an end, a deal that essentially paid for the News Corp. acquisition.

Recently, several key execs have left too, including COO Amit Kapur.

In general, the social-networking giant has had an air of decline about it, despite its still-enormous size.

Nonetheless, Murdoch had left the decision about the site’s leadership to Miller, his new hire, sources said.

Miller had been talking to many and was indeed leaning toward putting a new CEO in place, but not in this fashion. He had hoped to work out the transition with DeWolfe, said several sources.

Miller himself had been badly treated, when Time Warner (TWX) dumped him as CEO of AOL several years ago. Ironically, the media giant just ousted the execs who ousted Miller.

But Miller’s options narrowed last night, once TechCrunch ran a story claiming that News Corp. had hired a headhunting firm to “scour for possible replacements” for DeWolfe.

News Corp. hadn’t actually hired a headhunter at all, but the story spooked DeWolfe into calling Miller to ask what his plans were. That conversation led to today’s negotiations.

Van Natta is well known at News Corp. and was, at one point, the leading candidate to head up MySpace Music, which launched last fall, and the two sides held extensive conversations.

But Van Natta did not like the job’s org chart: Rather than a standalone company, MySpace Music is simply a unit of MySpace, reporting to DeWolfe.

MTV executive Courtney Holt eventually took the job.

Van Natta is intertwined with MySpace in other ways.

Project Playlist, the free music-streaming site he took over last fall, has seen traffic plummet after MySpace, along with Facebook, cut off the sites’ access to their users, a move prompted by lawsuits from several major music companies.

Van Natta has made some headway at extracting the company from its legal mess, which predated his hiring, and he has hammered out a settlement with EMI Music Group.

But Playlist is still being sued by other music labels.

And, even music sites that aren’t in legal trouble are struggling to keep their heads above water.

Thus, plenty of Silicon Valley watchers–including BoomTown, who calls Van Natta periodically to ask why he seemed to enjoyed the pain of running an online music business–have wondered why Van Natta landed at Playlist in the first place, and have speculated that he has been looking for a way out.

He has been on the short list for many big Web jobs at places like Microsoft and other Silicon Valley start-ups, but has not bitten until now.

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. Pittman will also join its board.

Playlist has previously raised several million dollars, said sources, but the new funding is many times that, to total about $18 to $20 million.

The move to Playlist is an interesting one for Van Natta, who has looked at a number of jobs since leaving the high-profile social-networking site earlier this year.

He has talked to a wide range of companies, sources said, including Microsoft (MSFT) and a range of start-ups, as well as with MySpace, which is owned by News Corp. (NWS). (News Corp. also owns this site).

Those talks between Van Natta and MySpace to run its new music initiative did not pan out for a variety of reasons.

But he has long expressed a desire to become a CEO of a company, rather than just head to another executive job within a larger company, so the move to run a start-up is not a surprise.

In an interview this afternoon, Van Natta told me he got very intrigued by the possibilities at Project Playlist, which was the first iteration of the start-up and in which he is an investor, due to its viral growth.

And, indeed, Playlist has grown quickly to become one of the larger music communities on the Web, claiming that more than 38 million music fans monthly, sharing playlists via its Web site and also widely distributed embeddable widgets. The site has tens of millions of daily page views, according to surveys.

To get to those big-scale numbers, Playlist essentially has offered users a giant linking service for music, not unlike Google (GOOG) with all information, pointing users to promotional, free and sometimes illegal music and music video tracks all over the Web.

Those links to illegal music have resulted in a lawsuit aimed at Playlist from the music industry, sources said, a sadly typical experience of many online music services.

The usual tactic for the music giants: Sue first and shake down later.

Under Van Natta, I would guess, Playlist is likely to reach out to music companies and strike deals.

The company also needs to settle on its main business plan, which appears to me to have been less important than its explosive growth.

Playlist currently does have some small amount of advertising on the site, and seems to be making most of its scratch from sending leads to ringtone sellers.

Van Natta did not want to reveal specific strategies for Playlist going forward, only noting the opportunity is large.

“Discovery around music is exploding on the Internet,” said Van Natta. “And the company that does the best job of taking advantage of that is really going to be huge.”

That said, there have been a lot of music-aimed efforts like Playlist in the music space, with a lot of different business plans and varying degrees of success, ranging from the Apple (AAPL) behemoth iTunes site, which sells single songs, to the CBS (CBS) music service, Last.fm, which relies more on advertising revenues.

Other contenders in the space include the Rhapsody subscription service from RealNetworks (RNWK), music discovery service iLike and many others. MySpace has also waded deeply into the music space, and Facebook is also reportedly weighing its own service.

Van Natta was one of Facebook’s earliest and most prominent execs, serving in jobs like COO and also Chief Revenue Officer while there.

He came to Facebook in the fall of 2005, after a stint as VP of Worldwide Business and Corporate Development at Amazon, and was part of the founding team of A9, the Amazon search company.

“I am excited to be building a company again,” said Van Natta, who has taken many months off since he left Facebook in February.