David Letterman’s Oprah Interview – Sex, Drugs & Jay Leno

david-letterman-oprahOn Sunday night, Oprah’s Next Chapter aired a fascinating interview with David Letterman,?host of?the Late Show?and possibly the world’s coolest man. With his characteristic charm, Dave openly discussed ball-buster issues including his sticky relationship with Jay Leno and?the?constant sex he used to have with Late Show interns.

Among the most interesting revelations from the interview is that Dave?considers a dick like Jay Leno to be not just his friend, but also?”the funniest guy I’ve ever known.”

?If you go to see [Jay] do his nightclub act, just the funniest, the smartest, a wonderful observationist, and very appealing as a comic.”

It sounds a bit kiss-assy, for sure, but Dave tempers it by going on to say that Jay is also “maybe the most insecure person I have ever known.” He then describes how they related?to each other when they were “kids,” and how their combativeness was par for the course as young, struggling comedians, but once transposed to the larger stage, it took on an uglier tone, at least as far as the public was concerned.

Dave maintains that the rivalry between Jay and himself is not the result of Jay having been chosen instead of him to replace Johnny Carson as the host of the Tonight Show. According to Dave, that decision was made by the network and was not a personal beef between the two comedians.

Oprah, who was on her A game for this interview, then?clumsily segued the?conversation?into?Dave’s 2009?sex scandal. In a bit of Clintonian double-talk,?Dave revealed that he sees a psychiatrist?to help him manage?the torment he had been experiencing over the?fact that?he wanted to consider himself to be “decent” man, despite being “capable of behavior that wasn’t coincidental to living a decent life.”

With a great big smile, Oprah clarified: “Are you talking about having sex or affairs with people in your office, is that what you’re talking about?”

To which Dave responded: “No, I’m talking about stealing cars.”

And that’s why we love him. To refresh your memory, a former producer for CBS tried to blackmail Dave into giving him $2 million in exchange for keeping quiet about?Dave’s extra-marital affairs. Dave famously refused the demands and chose to confess to his indiscretions live?on his show.?To Oprah, Dave?described his ulterior motives for his?public confession.

“In the back of my mind ? and this will give you the extent, the breadth and width of what a weasel I could be ? I was thinking, eh, maybe I can make this, maybe I can get a little sympathy out of this deal here.”

It worked because he came across as brave and human and repentent, and the public reaction was certainly much different than if he had lied or tried to cover his tracks.

Dave also discussed his struggle with clinical?depression and how it altered his perspective on it as a serious illness.

“I always thought, `Aw, you’re depressed? Go do some push-ups and you’ll feel better.??

To relieve his depression, he revealed that he takes a?”therapeutic dose of an SSRI,” which he credits … along with his son, his wife, and his?emergency heart surgery in 2000?… for making him the kinder, gentler man he is today.

Overall, the interview was slightly too mellow, slightly too “Oprah,” but it’s still incredibly cool?and entertaining to see an icon like David Letterman talking about himself, rather than interviewing other people, and addressing such personal issues. Fuck you, Jay Leno.


  1. dee says

    As far as I am concerned, both Leno & Letterman need to get off the air….. old news already……let’s try something new…..