Timberlake was sulky that day, but he made the ap en audition, blew away the judges and, along with fellow pop prodigies Christina Aguilera and Britney Spears, made it onto season eight of The New Mickey Mouse Club (a hotly competitive children's TV variety show). Lynn, incidentally, was also the person who came up with the name *Nsync for the boy band that would catapult her son to international fame.
The Justin Timberlake sitting in front of me in the summer of 2006 is a different creature to the man I interviewed three years ago, around the release of Justified. Back then there was obvious trepidation as to how the "new" Timberlake would be received. Back then, he was still half imagining critics would laugh him off stage.
"I was nervous, of course," explains Timberlake. "And I was surprised at how well Justified did. I mean, I was pretty determined. I was determined to put it out there in a big way."
And now? Well, it's clear he's more confident, more at ease with fame. It may have taken 15 years in front of audiences, but Timberlake is finally learning to trust his talent. It's a confidence that's also pushing JT to ensure his legacy is left behind. This year, he bought in to Stax Records, the legendary Southem soul label, home to Isaac Hayes, Otis Redding and Sam and Dave, among others. He has plans not only to sign local Memphis bands and launch them using his endorsement, but also take them on the road. Just as he does for the label, so he has big plans for his own career.
"This is me right now at my creative best," he tells me. "The first record may have been made with more from here" - he points to his heart - "but this record has been made more from here" - he points to his temple. "I don't want people to think I'm same sort of self-obsessed sex machine."
So does he feel older, more grown up, ready to settle down, perhaps? "Men are monkeys, man. Listen, as for marriage and so on... I have my two dogs for kids so you should ask them how I'm doing!" Then. perhaps conscious of the fact that Diaz is close by, he adds, "Never say never, but why ruin a good thing?"
Timberlake is well rehearsed at the smoke-and-mirrors game that is the celebrity interview. After all, he's been doing it almost as long as Arctic Monkeys have been alive. It can be frustrating guessing at his motivations, but perhaps the best glimpse into where Justin Timberlake is heading next creatively and emotionally comes from his work with Riek Rubin, the awesomely influential American producer who has worked with everyone from Run DMC and the Beastie Boys to Johnny Cash.
Rubin worked with Timberlake on several songs for the new album, though only one of them made the final cut. "Because they weren't good enough?
No, no, Justin felt that, I think, it was an entire separate body of work," explains Rubin on the phone from his LA studio where he is currently working on Linkin Park's new album, while als o developing a Johnny Cash video that Timberlake had a hand in devising.
"Yeah," says Rubin, "he had this idea to get loads of well-known artists from today - Chris Roek, Jay-Z, Brian Wilson, Kanye West, himself - dressed in a black suit and get them singing along to the song. It's a neat idea." The Rubin produetion that did make it onto FutureSex/LoveSounds, "Another Song", is the only ballad in what is otherwise a collection of hip-hop-infused dub bangers nearly all devised by rap producer Timbaland, the man behind the sounds of Missy Elliot, Nelly Furtado and Aaliyah.
Written by Timberlake, "Another Song" has no sweetener, no Pro Tools reverb on the voice, it's pure Rubin stripped back, raw, just Timberlake and soul legend Bill Withers' old band. It is, frankly, heart-wrenching, a full-on love song that Chris Martin would be proud of. Many, including Rubin, might guess that this was the next direction for the more mature but still "not-quite-ready-to-settle-down-yet" Justin Timberlake.
"I can't comment on that," chuckles Rubin. "But that authenticity he's striving for is within him. I've met many pop stars... and they can all entertain. But Justin has something else. We just have to wait till he's ready to show it."
And as Timberlake knows only too well, if and when he does decide to step away from the dance floor, one thing is for certain, the world will be watching: all eyes on him.
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This is right now at my creative best