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How Justin Timberlake Missed His Chance to Record With Michael Jackson

"I'm on the phone and I'm literally punching myself in the face," he recalled.

ByABC News
May 8, 2014, 12:30 PM
Justin Timberlake performs at Stade de France in Paris, April 26, 2014.
Justin Timberlake performs at Stade de France in Paris, April 26, 2014.
David Wolff-Patrick/Redferns/Getty Images

May 8, 2014 -- Justin Timberlake duets with Michael Jackson on "Love Never Felt So Good," from the late King of Pop's upcoming posthumous album, XSCAPE.

It's no wonder that he wanted to be involved in the project, since he's now revealed that years ago he turned down the opportunity to sing with the King of Pop himself out of loyalty to 'N SYNC.

In an advance clip from his appearance on "Oprah's Master Class" this Sunday, Timberlake told the story about how he originally wrote the 'N SYNC hit "Gone" on his own for Jackson to record.

When he learned that Jackson had turned the song down, he went ahead and recorded it with 'N SYNC for what turned out to be their final album, "Celebrity." But, as he recalled, Timberlake knew that particular record was different -- and that it was leading him down a new career path.

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"I think it's the first idea that I ever got about doing something on my own, because it was the first time I'd ever really felt the confidence to do it," he said. "And I knew that the music that I was interested and was writing at the time was different than what we had previously done. And it felt like a real departure."

Timberlake was then surprised to receive a phone call from Jackson himself. It turns out that he'd heard "Gone" after all and wanted to record it.

That's when things got complicated.

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"He said he wanted to cut the record, but he wanted it to be a duet between himself and I," Timberlake recalled. "And I said, 'Well, it's already out, we've already cut the song as an 'N SYNC record.' I'm on the phone and I'm literally punching myself in the face."

"I said, 'I can't do that. Can we do, like, 'N SYNC featuring Michael Jackson, or Michael Jackson featuring 'N SYNC?'" he continued. "And he was very absolute about the fact that he wanted it to be a duet between himself and I."

Of course, that never happened. But it's easy now to see why "Gone," coupled with that missed opportunity, led Timberlake to a solo career.

"Celebrity" was released in 2001, while Timberlake's solo debut, "Justified," came out the following year.