Justin Timberlake Ranks His Own Songs and Reveals the Surprising Stories Behind Them

He once hung up on Michael Jackson, thinking it was a prank call, and his label thought “SexyBack” would flop. The pop star looks back on the moments behind his biggest hits, and names his personal favorites.

Justin Timberlake has recorded countless songs, but when he was asked to rank his music, he called it “the most impossible task I’ve ever been asked to do.”

In a November 5 interview on Complex’s “Rank” series, Timberlake eventually revealed his top 10 favorite tunes, along with the stories behind some of his best-known songs. Here’s what came up.

“Cry Me a River”

The controversial 2002 track released following his breakup with Britney Spears took 10 minutes to write, according to Timberlake, who added that it may have only been five.

Though he never confirmed that the song was really about Spears, he told MTV News that year, “I will say writing a couple of songs on the record helped me deal with a couple of things.”

“SexyBack”

The initial response of Timberlake’s label to “SexyBack” wasn’t very encouraging, according to the singer. “They were like, ‘This is not going to work,’” he recalled. “‘You don’t sound like you. It’s too fast.’”

The reason Timberlake didn’t sound like himself was intentional. He shared that he deliberately masked his voice using effects so listeners wouldn’t recognize it immediately. Apparently, his label wasn’t convinced. “Every reason that they gave me that it wasn’t going to work was the reason that I thought it would,” he said.

“My Love”

Timberlake revealed that he originally asked Jay-Z to join him on “My Love,” but the music mogul declined, as he was already featured on Beyoncé’s upcoming song “Déjà Vu.” That’s when T.I. came into the picture, marking the beginning of a lasting creative relationship with the rapper.

“Gone”

Timberlake originally wrote “Gone” as a pitch for Michael Jackson, but it never reached the King of Pop. So he took it to NSYNC, only to get a call from Jackson after the song had already been released.

Timberlake thought it was a prank caller at first, and even cursed Jackson out and hung up, until he realized it was actually Jackson himself. He wanted to recut the song as a duet, but Timberlake declined out of loyalty to NSYNC. “I can’t turn my back on what I’ve already committed to with the fellas,” he recalled telling Jackson.

“Mirrors”

The song is inspired by Timberlake’s grandparents, who had married young but are still together. “It’s like a classic sort of Southern love story,” he said.

His Personal Top 10

When asked to rank his top 10, Timberlake chose “What Goes Around...Comes Around” as his favorite. He also finally clarified a long-standing rumor about the song being inspired by his breakup with Spears.

“It’s not a personal story from mine,” he said. “It’s actually a personal story from a friend that I asked permission to [use].” He also revealed he wrote the song in just about 20 minutes.

Here’s what emerged as Timberlake’s top 10, a ranking he called a “knee-jerk reaction.”

1. "What Goes Around...Comes Around"
2. "Mirrors"
3. "My Love"
4. "SexyBack"
5. "Cry Me a River"
6. "Rock Your Body"
7. "Until the End of Time"
8. "Pusher Love Girl"
9. "Strawberry Bubblegum"
10. "LoveStoned"

As for what’s next for Timberlake, it appears new music may be on the horizon. When asked what he was working on these days, he said, “I’ve been cheffing,” but teased, “All in due time.”