He won two Grammy Awards in 2007 for Best Rap Solo Performance ( `` What You Know '' ) and Best Rap\/Sung Collaboration ( `` My Love '' with Justin Timberlake ) . `` What You Know '' won a Grammy Award for Best Rap Solo Performance and was nominated for Best Rap Song at the 49th Grammy Awards . Also that year , T.I. collaborated with Justin Timberlake for `` My Love , '' which proved to be a worldwide hit , and won a Grammy Award for Best Rap\/Sung Collaboration with Justin Timberlake at the 49th Annual Grammy Awards and also won Best Male Hip-Hop Artist at the BET Awards for the second straight time .