#25: He Sparked the 2004 Super Bowl Controversy With Janet Jackson
On February 1, 2004, he performed with Janet Jackson during the Super Bowl halftime show. At the end of their duet, he pulled away part of her costume, exposing her breast on live television in front of one of the largest audiences in the country.

The incident quickly became known as “Nipplegate” and turned into a major media firestorm. Timberlake called it a wardrobe malfunction, but the moment became one of the most controversial live-TV events of the decade. The fallout, however, did not hit both performers equally.
