CAILLEY:

So when you’re sitting at home watching some good old-fashioned comedy from David Letterman, the last thing you’d expect to hear is a story about how he put his disco stick somewhere it didn’t belong. Shocking, yes, but really only because of one ever-so-important question: Who the fuck fucks David Letterman?

Good Lord, the man is 62 years old. That makes him old enough to be my father, or even a fairly young grandfather. So I make no apologies for saying I won’t do it with a man who has wrinkles in places I don’t even want to think about, no matter how many people tell me how exceptionally “experienced” he may be with age.

And when you really think about it, it’s hard to deny the semi-decent line of foxy men on the other late night shows that are infinitely more do-able than Letterman. Jay Leno is a stretch, but Jimmy Kimmel? Sure! (Bonus points if I get a cake that says “Congratulations on fucking Jimmy Kimmel!”) Jimmy Fallon? Sure, but only if he promises not to giggle while doing the deed. And Craig Ferguson? Oh hell yes. It’s an unwritten law that women swoon at the sound of a Scottish accent. Everyone knows that.

So in all seriousness, Smathers, I really don’t know what you’re going to say about the merits of bumping uglies with Letterman. And to be honest I really don’t want to know, since I don’t need night-terrors for the rest of my life.

JASON:

Is he sexworthy? Jesus, is that even a question? It’s like asking if Angelina Jolie has a display case of stuffed foreign children — we all know it’s true, but we don’t go around talking about it.

Listen, this man has been in the late night talk show business longer than anyone alive today. And as such, he’s sat down with a lot of celebrities on and off camera. Given the sheer amount of time he’s been doing it, and the law of averages, you’ve got to assume he’s gotten around. With celebrities. Sexually. With his penis. (I assume?)

What, you think I love Dave for Dave? Just because medieval Englishmen thought gap-teeth was a sign of lecherousness (and I guess that would apply to people like Madonna), doesn’t mean I do. I need a higher grade of starfucking.

But I’m not gonna get that. Tom Cruise isn’t actually gay (he just has an fetish for lobotomy patients), Julia Roberts is actually a horse and Russell Crowe would probably crush my fragile bones. I guess I could settle for Kathy Griffin, but she’s actually busy taking any possible other prospects off the market.

So, the best chance I have is to have sex with a celebrity who’s had sex with a celebrity. Since Conan O’Brien is more god than man, Craig Ferguson hasn’t been as lucky with A-list celebs and Jimmy Fallon is functionally a eunuch, Dave’ll do.

Now if I can only get a job on his staff…

TONY:

The real question here is why would I only do Letterman, when I can do the talk host three-way tango. But who is the lucky third?

Leno has the prestige and he’s a car guy so you know he likes it fast, but that chin worries me. Something that big you know he is going to want to use it in freaky ways, and I don’t want to spend half the time protecting particular orifices.

I’ve always been drawn to European accents, so Craig Ferguson is a possibility. Kimmel… no. Carson Daly would bring back flashes of my “TRL” days and that would just be an awkward, prepubescent mess with embarrassing “I Want It That Way” climaxes. I’d go into Conan, but that’s just going to bring up carpet matching the drapes questions and I don’t want to sully the good O’Brien name.

So who’s left? The shy, fresh meat of Jimmy Fallon. The matchup is perfect. Letterman’s extortion scandal proves he is a domineering TV stalwart and Fallon is a timid newbie. I can picture it now. Letterman playfully flicking his tongue over that gap. Fallon doing that awkward sway of his.

Fuck… I need to take a shower. I feel dirty.