U: U.S. Marine Corps Birthday Ball
United States Marine Kelsey De Santis uploaded a video to YouTube asking the singer to be her date at the Marine Corps birthday ball. Of course, the video went viral and JT himself responded in the affirmative. On November 13, 2011, Timberlake attended the ball with Santis and Mila Kunis, who was also invited via YouTube by Sgt. Scott Moore. It was a star-studded affair. If only for a night.
V: Video Music Awards
Without MTV, Timberlake would hardly have the career or legacy that he has today. In the era of the music videos, N SYNC and JT himself produced some of the generation’s most iconic videos. As a result, he became a regular feature at the VMAs, first appearing in 1999 on stage with Britney Spears. In 2002, he performed for the first time solo. And then in 2013, his most celebrated and hyped performance featured the 110-second reunion of N SYNC. It was the highlight of the summer that, sadly, ended as quickly as it began.
W: Wardrobe Malfunction
In February of 2004, JT made his way through his second Super Bowl halftime performance (the first being with N SYNC in 2001). All was going according to plan, until the infamous wardrobe malfunction exposed Janet Jackson’s breast causing a media frenzy, a then-record number of FCC complaints, lawsuits, fines and backlash. It was as if the world had never seen a (covered) nipple before. Has there ever been a more defining moment in two singers’ careers? No, unless you consider Kanye West and Taylor Swift. But that’s another list for another day.
There was a time when Christina Aguilera rebranded herself as Xtina, the girl who was dirrty. That phase just happened to coincide with Timberlake’s transition as a solo artist. And who is he to turn down the chance to co-headline a tour with the pop singer? For one brief summer (as if a kiss off to Spears), Xtina and Timberlake had a fling on stage – sharing the spotlight and entertaining fans around the country.
In the late-00s, getting discovered meant taping yourself singing covers of pop songs and uploading it to YouTube. That’s what Esmée Denters did. The Dutch singer was discovered after her covers went viral on the web. By 2008, Timberlake was knocking on her door and signed her to Tennman Records (see: O). Denters became his first artist and protégée and even sang on the single, “Follow My Lead.”
Z: Z, Jay
2013 will likely go down as the year known as the time JT and Jay Z took over music. Not only did the two release three new albums, they collaborated on four original songs (including “Suit & Tie” and “Holy Grail”) and went on tour together. These two have staked their claims as the kings of R&B and hip hop, respectively, and there’s no one looking to take the crown anytime soon.