Last night on NBC’s The Tonight Show, Jay Leno was doing his Monday night “Headlines” segment when he held up a TV Week cover with a picture of himself and a cutline that said “Host of The Tonight Show on ABC”. When the few laughs died down, Leno looked into the camera and smirked, “It’s like a headline from the future.”

Look, I’ve always thought that Leno and ABC were a logical fit when he leaves NBC (notice I don’t say if he leaves NBC) next year. Yes, Fox gets more ink as his possible next home. But ABC doesn’t seem to want edgy programming, so Leno’s exaggerated mainstream appeal makes sense for the network — even if his advanced age doesn’t. Here’s the problem with both Fox and ABC for Jay: he wants to go head to head with Conan and Letterman. So Nightline would be history.

Back in 2002, Disney’s Bob Iger was ready to jettison the late night news show in a heartbeat if he could lure David Letterman away from CBS. It almost happened — that is, until word leaked out that Disney was axing ABC’s best news program starring its best news anchor Ted Koppel. There was a shitstorm of protest.

nbc-logo-rgb-pos2.jpgThen, in 2004, Iger sought again to steal a late night host — this time, Conan. That was when Zucker, in order to keep O’Brien at NBC, promised to make Conan host of The Tonight Show in 2009 — thus explaining the origins of Leno’s non-stop animosity towards the pint-sized Big Media prez/CEO. Given that Leno is still the late night ratings leader, Iger is circling, along with Fox and Sony television. After all, Koppel’s gone, and Nightline is an afterthought.

So that leaves just one more question mark: Jimmy Kimmel. ABC is extending its option with him by another year, keeping him at the network through at least 2010. But that’s also the earliest date that Leno under his NBC contract terms can start working somewhere else. Kimmel could stay in his time slot if Leno does just a 30-minute show, agree to do a later show, or move to Fox and do an earlier and edgier show. See, this wasn’t so hard to figure out… Stay tuned.