Yesterday, I wrote a piece entitled “Why Conan O’Brien Wouldn’t Work on the Web … Yet.” After reading the next round of rumors about how the NBC nighttime lineup is shaking out, I feel like I need to re-phrase my analysis and predictions a bit.

First of all, to the rumors: according to Sean P. Aune, who’s been doing a fantastic job chronicling these moves at his personal blog, the current rumor is that NBC is going to fork over the enormous sums of cash to release Conan from his contracts with the Tonight Show and give the show back to Jay Leno. While reading that rumor (after having read a fascinating rather long bit explaining the backstory of the late nite wars of the last 50 years), it occurred to me that there is no way that Conan O’Brien, wherever he moves to, is going to retain the “Tonight Show” title or trademark.

Given that sad (what appears to be) truth, I’d like to revise my statements, as they were in the context of Conan, the “Tonight Show” format, and the “Tonight Show” brand all moving as one, to say that now might be just the right time for Conan to think about moving online.

There are, however, some things Conan should probably consider before he makes such a move.

Conan’s Audience Online, While Large, Will Be Smaller Than His TV Audience

There are only one or two obscure platforms or setups that function in the living room that provide anything close to the veg-factor experience through digital means. By that I mean that Conan and the “Tonight Show” traditionally has prospered quite a bit thanks to people being too lazy to turn off their televisions after the local news is on.

In all my years of trying to explain the term “veg-factor,” I’ve been using all these crazy examples that most of my audience can’t relate to (like morning television, Jeopardy, day-time programming quirks and many others).  The truth of the matter is, though, that the entire history of late-nite talk shows has been built on the concept of the veg-factor, and people being too lazy to turn off their sets.

Currently, almost no set-top box provides this experience, and as such digital programming is at war with itself.  The short form video works best online, because online audiences are media-snackers. Many of those shows have crossed over to the living room successfully, but limit the scope of their growth since the viewer is wanting to have a long-form experience rather than switching videos every 4-8 minutes.

Which leads me to my second point:

Conan Should Decide on a Target Audience: The Computer Screen or the Living Room

It’s going to take a very savvy digital team to make such a transition work (while not leaving any audience slices on the table). He’s going to have to decide on how the long form version of the show would look, and then have either re-worked short form videos for the YouTube and embedded video markets, or re-cut versions of the daily show for online audiences.

He’s going to have to identify not only existing ways to get into the livingroom digitally, but new and emerging ways as well.  When I think back to what I saw during CES, I can off the top of my head rattle off a handful of ways to get there: just about every console gaming platform, AppleTV, iTunes, the Roku, Netflix, Boxee, and Sling. There are probably quite a few more I’m forgetting.

How’s he going to get all those places?  Even the most savvy amongst us New Media producers aren’t everywhere yet.

He’s going to need a crack team of digital media folks to get him there.

Conan Can Still Make a Mint Online

Online CPMs for video can easily range between $10-60.  If it’s a longform show with an in-house sales team, it can be the higher end of that scale, or even far exceeding that number. Conan has mainstream appeal, and if he had a team that truly fired on all cylinders (with a complete web presence, tools for sharing, allowed embeds of the show, and really researched the set-top distribution side of the equation), while he still won’t be making what he’s alleged to be getting for quitting at NBC, he’d still be doing what he ostensibly loves and making a pretty decent wad of cash in the process.

I’d love to see Conan go online. Unshackled by the constrains of traditional TV and it’s traditional formats, he could be the first true independent breakout case study for New Media, taking all the concepts and methodologies mainstream.