All Things Digital

Lloyd Braun–the former Hollywood super-programmer turned Yahoo entertainment czar turned Hollywood and online programmer–has signed a multimillion-dollar deal to make an original destination site for Microsoft’s MSN portal, aimed at aggregating celebrity, entertainment and pop culture news, according to several sources.

With the still-unnamed site, MSN plants its own Paris Hilton flag in a very crowded field, which has numerous competitors such as People.com, PerezHilton.com, AOL’s TMZ.com, PopSugar.com and Yahoo’s OMG.

It is also interesting that Microsoft (MSFT), which has focused its efforts of late on its technology, especially related to online advertising and search, is making another foray into the content arena via MSN, where it has had mixed results in the past.

Ironically, Braun (pictured here) was the exec who green-lighted the OMG site, which aggregates celebrity-oriented content and has since become a big traffic success for Yahoo (YHOO).

The deal, which will be announced tomorrow, will be a joint venture with Microsoft and BermanBraun Media–an independent multimedia production company headed by Braun and also former Hollywood studio exec Gail Berman.

Braun left Yahoo under a cloud, after clashing with his superiors who had brought him in to make new online programming, as he is doing now.

But that has not stopped Yahoo from making its own deal with Braun, sources said, a much smaller effort to produce a daily “Lunacy Report.” The deal has not yet been announced, although it has been signed.

That online project will be focused on “weird news,” which is an amazingly huge driver of page views on Yahoo’s news site–almost 7%–featuring stories like one today about a man who was jailed for faking his own death.

The video-heavy “Lunacy Report” will have Vance DeGeneres, who is the executive producer of the HardlyNews online parody site and also brother of Ellen DeGeneres, as its host.

But the MSN deal is a much larger one, requiring BermanBraun to staff up, and it already has many former Yahoo employees involved in the project, sources said.

That’s because, akin to a regular Hollywood production studio, BermanBraun will be building both the front and back end using Microsoft technology. Both BermanBraun and Microsoft will be selling ads for the site.

But it is Microsoft that will be footing much of the multimillion budget for the site–to launch in early 2009–and will own it outright. It will get support on the main MSN page and also throughout the service.

Advertisers briefed on the project said the site is aiming for higher integration of branding than just simple display ads, looking for innovative ways in which marketing messages are integrated into content.

And it will be designed to be much more interactive to spur more engagement. In fact, the new site does not look like a typical MSN site, said sources who have seen it, with a highly stylized design and a wide range of applications.

Braun was reportedly pitching advertisers last week in New York, who said he described it as focused on the wider pop culture scene and not just on celebrities, which is an area of much user interest online.

It is not clear if PepsiCo (PEP) will be a major advertiser yet. BermanBraun announced a deal last July with Pepsi to support original entertainment content developed for online platforms.

The entertainment and marketing arm of the beverage giant has a “first-look” at BermanBraun online projects and has a chance to fund and sponsor original online content it produces.

What will be most interesting will be what happens to the new MSN site and OMG, if Microsoft and Yahoo do manage to strike a merger deal at some point, despite a failure to do so thus far.

Why does the idea of a marriage between Hollywood writers and VCs make me slightly queasy?

But that’s just the feeling I got when I read the always sharp Joseph Menn of the Los Angeles Times, who penned an interesting piece earlier this week about writers in Hollywood turning to venture capitalists as the strike drags on.

Wrote Menn: “At least seven groups, composed of members of the striking Writers Guild of America, are planning to form Internet-based businesses that, if successful, could create an alternative economic model to the one at the heart of the walkout, now in its seventh week.”

That includes meetings with Silicon Valley VCs like Jim Breyer of Accel Partners, whose investment in Facebook gives it insight into the creation of new audiences.

The hope for the–let’s just say it, shall we–unnatural pairing of tech VCs and Hollywood folks?

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