You want awkward? Check out the clip below from last night’s Jay Leno Show, which concludes with the host surprising guest Chelsea Handler by lowering down a giant-sized reproduction of her forthcoming Playboy cover. Actually, the awkwardness starts straight away with Jay raising the subject of his fellow comic and chat show host having posed for Hef and Chandler responding with a slightly irritated, “Why are you bringing that up?” Elsewhere in the clip Handler mentions that her father thinks she is “very sexual” and cracks a joke about Letterman. There is also mucho talk of the comedienne’s drinking habits, but that pretty much goes without saying. And then, finally, comes the unveiling of Handler’s cover, which I wouldn’t dream of commenting on, except to say that she’s no Marge Simpson (who graces the cover of the current Playboy, or so I’ve been told by people who know about that sort of thing).

Frankly, it seems unlikely to me that Leno really would have “surprised” the feisty Ms. Handler with her own cover in such a manner, except for the fact that she does seem genuinely stunned and annoyed. And I’m not sure she’s that good an actress.

Do you think this is all for real? Will you be checking out Handler’s Playboy issue? And is this the most fascinating segment that has appeared on Leno so far?