A visibly uncomfortable Justin Timberlake made his first appearance on LATE SHOW WITH DAVID LETTERMAN last night (11SEP06), where the talk show host grilled him relentlessly about girlfriend Cameron Diaz, smoking pot and the Janet Jackson "wardrobe malfunction" in quick succession. Timberlake performed his hit single SEXYBACK with Timbaland and then sat down for what was supposed to be a short, light-hearted chat. Letterman started off by saying, "You said you don't mind talking about Cameron Diaz." Timberlake said, "We can talk about her. She's lovely. I mean, I don't want to go into details..." Letterman shot back, "But that's what we want - the details!" The talk show host then proceeded to interrogate him, asking how long they had been dating, how they met and what they did on their first date. Letterman then asked him about a Rolling Stone magazine cover story where he smoked marijuana with the reporter while he was on tour in Amsterdam saying, "And in it you're smoking weed with the guy, is that true? During the interview?" A stunned Timberlake tried to come up with an answer, eventually saying, "Um, I make a promise to you that I try not to do drugs while I'm doing interviews." Without missing a beat Letterman continued with, "Now tell me about the Superbowl thing with Janet Jackson." An exasperated Timberlake kept shaking his head and putting his hand in his heads, saying disbelievingly, "My first time on the damn show!" Letterman insisted the whole Superbowl incident where Jackson's breast was exposed on live TV looked like it was premeditated, with Timberlake defending himself saying, "I don't think we meant for it to go like it did. But the actual choreography was obviously planned. I think it's fair to say that was not a well thought out performance." Letterman shot back, "Yeah, it's a small gig, don't put any thought into that!" When the talk show host shook his hand and thanked him for coming on, Timberlake said sarcastically, "Hey, it was a lot of fun."