One of the biggest Rap features of 2006 nearly went to Jay-Z instead of T.I. The latter's appearance on Justin Timberlake's "My Love" helped turn the record into a defining hit for both artists, but he wasn't the singer's original choice. It turns out that getting Hov on the track was a little more complicated than making the request. The missed collaboration has returned to the conversation with Timberlake's appearance on Complex's Re-Rank, released Thursday (Nov. 5).
Timberlake previously explained the situation during a 2013 appearance on The Breakfast Club. He had approached Jay-Z about contributing to his sophomore album, FutureSex/LoveSounds, but the rapper wasn't interested in adding another guest appearance to his schedule.
"I wanted to do a record with him on FutureSex/LoveSounds," Timberlake recalled. At the time, Jay-Z had already recorded "Déjà Vu" with Beyoncé, and Timberlake understood that he wanted to limit his features while focusing on his own music. The refusal wasn't personal. Timberlake respected Jay-Z's decision and eventually brought T.I. onto "My Love," a choice he later described as a blessing in disguise. Praising the Atlanta rapper's contribution, he said his verse was "phenomenal."
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Justin Timberlake And Jay-Z Eventually Made Their Collaboration Happen
Released in 2006, "My Love" became the second single from FutureSex/LoveSounds. Produced by Timbaland, Nate "Danja" Hills, and Timberlake, the record reached No. 1 on the Billboard Hot 100 and remained there for three weeks. It also earned the artists a Grammy for Best Rap/Sung Collaboration in 2007.
T.I.'s involvement helped establish a musical partnership that continued beyond the record. Timberlake later returned the favor on "Dead and Gone," which appeared on T.I.'s 2008 album, Paper Trail. The collaboration reached No. 2 on the Hot 100 and became another major commercial success for the pair.
Jay-Z and Timberlake eventually found their own chemistry in the studio. Their 2013 collaboration "Suit & Tie" became the lead single from Timberlake's The 20/20 Experience, while "Holy Grail" appeared on Jay-Z's Magna Carta Holy Grail that same year. They also embarked on the joint Legends of the Summer stadium tour. Then, in September 2026, Timberlake joined Jay-Z onstage in Paris for a rare performance of "Holy Grail" during the rapper's 30 Tour. The appearance reunited the collaborators nearly two decades after Jay-Z passed on the opportunity to appear on "My Love."
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