I will miss David Letterman very much after he retires in 2015.
His legacy will stand as one of the most talented and influential late night hosts in TV history, second only to Johnny Carson.
Letterman's retirement puts CBS in a tough spot unless they absolutely, completely believe Craig Ferguson, the host whose whole show is based around breaking the conventions of the late night format, can move up to 11:30 and win over a mainstream audience. To do this Craig will have to either convert the new viewers to his unconventional style or "evolve" his act to win them over and potentially risk alienating his core following. That puts CBS in a position to make the hard choice of promoting from within or bringing in a new man.
Forget the arguments about race and gender surrounding this issue in the press written to fill column space online. CBS should have only one goal in choosing a replacement for Letterman: Do not pick any man or woman (regardless of race) who will have to retire before Jimmy Fallon.
That's your only goal CBS, apart from picking a decent name that can entertain people during that time. You need him or her to outlast or tie Jimmy Fallon in duration for the next two decades or more.
Here's the facts: Jimmy Fallon is 39. And that's the only fact that matters.
Jimmy Kimmel is 46 so he's already the old guy at 11:30 as of 2015.
You need to beat that CBS.
So that means Jon Stewart, Stephen Colbert, Louis CK, Ellen DeGeneres,
Jerry Seinfeld, Chris Rock and any young Baby Boomer are all out of the running.
If CBS has to name a another new host for the Late Show in ten or twelve years because they are turning 67, like Letterman now, while Fallon is in his prime - it's over.
The competitive balance maintained during the Leno/Letterman years needs to continue into the new generation and NBC went for a long term solution in Fallon like they did with Carson back in the 1960's. That's why I think CBS should try to plant the smartest, youngest flag possible in the late night ground.
Neil Patrick Harris and Chelsea Handler are both 40 so they should be considered contenders. Harris seriously due to his level of popularity, skills and wit and Handler for political and public relations reasons because I'm not a fan of her work. Tina Fey is 43, super busy and doesn't need this job.
I think Kevin Hart, 34, would be a perfect choice to win the new generation but with his film career blowing up in an Eddie Murphy in his prime kind of way I don't think he's a contender anymore either.
Here's my out of the box, free, no-cost, pay as you exit pick for CBS and the Late Show job:
Jason Segel, 34, former star of HOW I MET YOUR MOTHER.
Segel is funny, smart, a screenwriter and performer with musical talent.
His work re-launching the Muppets as a film franchise for Disney shows that he understands and appreciates a beloved franchise like The Late Show. Like Fallon he has a group of cool Hollywood insiders as his best friends to call on and do fun viral activities that will carry his TV brand to the internet. The CBS audience already loves him as a member of their TV family. CBS brass may or may not love him due to his tough contract negotiations during the HIMYM series but at 34 years old, 5 years younger than Fallon, he's a guy who can run 25 years or more on the show for the network. By hiring him CBS gets to promote from within and bring in a new man at the same time.
The late night market is segmented so heavily that a decent "name brand" can compete and make it close in the same way Leno and Letterman ran for decades. A network can be happy with either the young demo or total numbers. It's hard to win both but a performer like Segel could be the answer that CBS so desperately needs to its most important question right now.
P.S. to CBS, if you don't pick Jason just pick Neil Patrick Harris and you'll be fine. The next real big late night question is what are you going to do to compete with Carson Daly and Later?