Justin Timberlake: Leaving 'NSYNC Was 'Bittersweet'

Justin Timberlake's decision to leave 'NSYNC over a decade ago may have seemed like a no brainer in hindsight. But at the time, his departure was not necessarily a foregone conclusion. Timberlake recounts wrestling with his agonizing decision as part of Oprah Winfrey's Master Class series:

"I would wake up every morning feeling this urge to step out on my own and try my own hand as a musician just by myself," Justin said. He also found himself questioning that urge:

"It was happening all around me. 'Why wouldn't you ride this out? You're the biggest group in the world, why would you walk away from this?'"

Ultimately however, it was inspiration from the King of Pop himself, Michael Jackson, that finally encouraged Timberlake to strike out on his own. As previously reported by The Inquisitr, the former 'NSYNC member describes the song that planted the seeds for his departure:

"The first real seed of that was called "Gone". It ended up on ['NSYNC's] third and last album. And it was the first song I kind of cut by myself and then brought it to the guys to include them. But I originally wrote it for Michael. I originally wrote that song for Michael Jackson."

Timberlake continues, detailing the agonizing chain of events that followed.

"So we decided to cut it," he said. "But it was one of those songs that felt a little more personal to me because I wrote it for the biggest artist of all time."

What happened next changed the course of Justin's career forever:

"I guess Michael did hear it, and called me on the phone and want to cut the record but he wanted it to be a duet between himself and I. And I said, 'Well, it's already out. We've already cut the song as an 'NSYNC record.' And I'm on the phone and literally punching myself in the face."

Timberlake then tried to recruit Jackson into performing "Gone" as part of an ensemble with the rest of 'NSYNC, but Michael insisted that he would only wanted to do it as a duet with Justin. Jackson's steadfastness provided the first inkling, according to Justin, that he should strike out on his own, having gained the confidence from his conversation with Michael.

Ironically, Timberlake is finally getting his wish of dueting with the King of Pop, albeit, after the legendary artist has already passed away. Justin's new video for "Love Never Felt So Good" features him dancing with Michael Jackson and contributing vocals to the song.

As for his time with 'NSYNC and the decision to leave the group, Timberlake calls it "the best/worst thing" he's ever done.

"It was bittersweet. It was hard to say goodbye to that era, but I felt it changing. I felt music changing. And I felt myself changing."

Watch Justin Timberlake talk Michael Jackson and 'NSYNC on Oprah Winfrey's Master Class below: