Letterman Puts Justin Timberlake on the Hot Seat

09/12/2006 at 02:00 PM EDT

Letterman Puts Justin Timberlake on the Hot Seat
Timberlake on The Late Show on Sept. 11
JP Filo/CBS/Landov
During Justin Timberlake's first-ever appearance on The Late Show with David Letterman, the host grilled the pop star Monday about his relationship with Cameron Diaz, alleged drug use and his controversial Super Bowl performance with Janet Jackson.

Timberlake, whose sophomore solo album FutureSex/LoveSounds is out Tuesday, appeared on the show to perform his single "SexyBack" with rapper-producer Timbaland. But after the singer's performance, Letterman immediately put him on the spot saying, "You said you don't mind talking about Cameron Diaz…"

After the famously private singer answered that he didn't want to go into detail about his girlfriend of three-plus years, Letterman shot back, "That's what we want – the details."

Though the 25-year-old pop star tried to laugh off Letterman's personal questions, the host didn't let up. He went on to ask if Timberlake did indeed smoke "weed" with a Rolling Stone reporter who interviewed him in Amsterdam, as had been reported.

"I make a promise to you I try not to do drugs while I'm doing interviews," the singer, who was noticeably uncomfortable, replied with a laugh. He then joked, "I'm completely drunk right now."

Next, Letterman asked the singer about his controversial halftime performance at Super Bowl XXXVIII, during which Janet Jackson's breast was exposed on national television.

Timberlake threw his hands up in the air and looked around in amazement, as the crowd laughed and applauded.

"Isn't it great to sit on the couch?" Letterman sidekick Paul Shaffer asked. To which Timberlake responded, "I know, right, my first time on the damn show!"

An undeterred Letterman continued, "It was all part of the deal, right? It was all planned, pre-meditated? As I recall you made a move to, uh (as the host made a pulling gesture). But what was supposed to happen? Doves were supposed to fly out? Release the doves!" Letterman said.

Eventually, Timberlake conceded, "I think it's fair to say that was not a well thought-out performance."

As the interview wrapped up and Letterman thanked the singer for appearing on the show, a relieved Timberlake replied, "Hey, it was a lot of fun."

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