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.

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?

That the sour lemons being thrown between studios and writers–ironically over future Internet revenues–will actually yield delicious lemonade, spurring the creation of quality online programming using the Internet’s massive distribution system that could also make lots and lots of money.

“Could” is obviously the operative word here, because–as we have noted many times in this column–very little original content created on the Web has had any true payoff yet.

Um, well, none, actually. (Save porn, which is an almost perfect content format for the Web.)

To be fair, there have been promising signs.

Ex-Yahoo exec and Hollywood player Lloyd Braun struck a deal with PepsiCo to pay for and create online content.

MySpace has been backing a range of online-only shows made by Hollywood types (although none has shown strongly increasing popularity and even seem to display worrisome declines in viewership, despite the justified potential touted by creators).

Of course, there’s the high-profile Sequoia Capital-backed and Will Ferrell-fronted FunnyorDie.com, as well as MyDamnChannel.com, from former MTV executive Rob Barnett.

And Viacom agreed this summer to create a new online entertainment studio in a 50-50 split with the creators of the popular “South Park” TV program.

Finally, Creative Artists Agency, which is the biggest talent agency in Hollywood, is apparently working with Silicon Valley VC firm Draper Fisher Jurvetson to raise up to $200 million to invest in the digital entertainment sector, even as other such firms as UTA and William Morris are making similar moves.

While that is a very little amount of money considering the billions of dollars that slosh around Silicon Valley to fund things like dopey widgets and yet another movie-comparison site, it is still a start.

The presumable goal is that by creating and distributing content for the Web in a lower-cost way, many kinds of revenues could be garnered via everything from advertising to getting back investments by selling the online material to television and the movies.

That sounds like a plan, except for the fact that the current state of advertising innovation related to Web videos is quite nascent, even pre-fetal.

While a lot of companies are focusing on this and advertisers seem willing to move in the direction of more online ad spending, it will simply be a long time before these investments pay off.

Which is just not part of the no-risk-and-all-reward mentality of most players in Hollywood, who wouldn’t know a start-up unless it took their prime table at the Ivy.

In all seriousness, it seems unlikely that the high cost of production now in place in the entertainment industry would in any way lend itself to the critical need for that kind of massive shift in economics required to make online content pay off now.

Currently, studios still only grudgingly want to consider sharing ownership of content, and the talent seems even less willing to take the burden of risk required onto its shoulders.

Still, I admire all the efforts on the part of writers to not just strike, but strike out from their current comfort zone and move into the future, where online entertainment production and distribution seems obviously inevitable.

The problem is that it might take a longer while than those creators have patience for and they will prematurely abandon their efforts and return to propping up a system that is destined for, while not oblivion, then certain diminution.

So what’s needed–as in all marriages–is a crazy leap of faith, like this one from “Heroes” Peter Petrelli on NBC.

I am definitely no expert on this topic, except to say that the problem is that the delta between falling flat and succeeding is frighteningly close.

In other words, I Has No Idea what to do.