Jay Leno Creeps Chelsea Handler Out – Reveals Chelsea’s Playboy Cover

Chelsea strikes a Playboy pose with a touchy-feely Leno.

Here is a tweet I just so happened to see before watching The Jay Leno Show this Wednesday, October 28:

@ChelseaLately: If you watch the Jay Leno Show tonight, you’ll notice that Jay was obviously hitting on me. Awkward.

Honestly, I foresaw this. Okay I didn’t, but I had a hunch that Leno would somehow act too “friendly” towards Chelsea Handler on his show. I don’t know why. There is no big connection between the two. But she is an independent, pretty, and funny woman, and how could anyone not like her for that? Many people find these qualities in her to be attractive. She is also one of the only female comedians to host her own late night TV show, which is automatically earns her respect. As it turns out, Handler announces during her visit with Leno that she will be on the cover of Playboy’s upcoming December issue. Maybe Leno found this news to be too exciting.

If she finds Leno to be awkward, then I’m not sure how she is going to live after having revealing photos of herself be published in the upcoming weeks. Perhaps we can call her interview a “test run.” She will certainly have more men oggling at her in December.

But Handler is already taken. She is known for making jokes about her boyfriend, Ted Harbert, who is the president and CEO of Comcast Entertainment. Naturally she makes more jokes about him on The Jay Leno Show, which are instigated by Leno for asking Handler if she is still single (she and Harbet briefly broke up but are together now). As a comedian speaking about her man, she is entitled to throw a few jabs for laughs.

Chelsea and her man Ted Harbert

Leno seems to enjoy these remarks and jumps in on the fun calling her boyfriend an old grandfather, someone who went to school with Hugh Hefner and that he rides a rascal scooter. Ouch. Who knew Leno could be so competitive over a woman. It’s like watching a PBS nature program where a male wildebeast competes with another male wildebeast for the attention of the female wildebeast.

Leno’s jokes go too far and provokes Handler into doing something that we rarely see: exalting her boyfriend. Handler doesn’t like to be anyone’s bitch. That includes Leno. While at the beginning of the interview she is neutral, after Leno’s teasing, she clearly goes on the defensive. This is when Leno makes the leap from going too far to downright creepy. After forcing a confession out of her about her nude pictorial in the upcoming December issue of Playboy, Leno asks her another series of creepy questions like: “What does your father think of the Playboy spread?” (okay, Jay)

Leno asks her if she wants to see the Playboy cover (having gotten it from Hefner himself). When she says emphatically “no”, Jay gives a response that is talk show gold (and… yeah… creepy):

“Well here’s the thing: nobody cares what you think. See, you are too use to getting what you want. What you need is a guy to say “no.”

You see, Leno is that guy that says “no.” Chelsea calls Leno out:

“This is a very interesting side of you, Jay. Now everyone is finally starting to realize that you are exactly like Dave Letterman.”

SLAM! The audience goes wild over this joke. It will go down in talk show smackdown history. Chelsea Handler is nobody’s bitch.

Leno grabs Chelsea’s hand and takes her to the unveiling of her cover. Yes, she looks beautiful on the cover. And yes, though it was great tv, it was (as Handler said) awkward and (as I said) creepy. We like our Leno non-sexual please.