Credit: Alamy / Gage Skidmore

Justin Timberlake proved his solo success was no fluke in 2006 with FutureSex/LoveSounds. Four years after Justified, which was filled with hits like ‘Senorita’, ‘Cry Me a River’, ‘Rock Your Body’, and ‘Like I Love You’, the singer took a further step away from NSYNC with a bold new direction. FutureSex/LoveSounds was also stacked with giant songs, but you might not know that Jay-Z was almost featured on one of its biggest records.

JT scored more chart-toppers worldwide with songs like ‘SexyBack’, ‘What Goes Around… Comes Around’, and ‘My Love’, featuring a memorable verse from T.I. The Atlanta rapper spits in the first lines, “Shawty cool as a fan, on the move once again/ But he still has fans from Peru to Japan.” It’s one of those rap verses on a major pop song that even non-hip-hop fans know all the words to.

Despite how well it worked, T.I. wasn’t the first choice for ‘My Love’. Timberlake attempted to recruit Jay-Z instead, but he declined. It had nothing to do with disliking the beat from Timbaland, either. At the time, Hov wasn’t doing many features and had already collaborated on a song with his wife, Beyoncé, which became a smash hit.

“I wanted to do a record with him on FutureSex/LoveSounds and he, at that time, had done a record with Beyoncé, it was ‘Déjà Vu,’” he told The Breakfast Club. “And he said—respectfully, I can’t knock him for saying like, ‘I have this one feature.’ I think he was working on his own music as well so he didn’t want to be on too many things. And I said, ‘I totally respect that. I’m obviously not gonna get into any domestic anything. That’s your wife.’”

Revealing the track he was supposed to be on, he said, “The record was ‘My Love.’ And it ended up being an interesting blessing in disguise because I think Tip for that record—I mean, his verse is phenomenal.”

In another interview with Vanity Fair, he claimed Jay-Z offered to work with him on his next album. But Timberlake had a now-or-never attitude, stating that the song felt right to him and that the opportunity might be lost due to the gaps he takes between each album.

“Jay-Z has put out 11 albums, and I was talking about doing a collaboration with him, and he said, ‘I can’t do it right now, but I’ll get you on the next album,'” he recalled. “I was like, ‘No, man, I don’t work like that. This sounded good to me, for you and me to do together, and if it doesn’t work, then I totally get it. But I won’t be putting an album out next year; these aren’t a dime a dozen to me.'”

Despite Timberlake’s stance, they collaborated on his next album, The 20/20 Experience. The pair teamed up on the hit single ‘Suit and Tie’, one of their biggest songs. Not only that, but they also went on tour together that year. The Legends of the Summer Stadium Tour supported JT’s album and Magna Carta Holy Grail, becoming the 15th highest-grossing tour in 2013.