Will Smith rode the waves of mainstream pop culture masterfully, graduating ever upward in icon status as he developed from teenage rap sensation to sitcom phenomenon to Hollywood blockbuster star. As a musical presence, Smith maintained his wholesome take on rap from his mid-'80s multi-platinum hip-hop duo DJ Jazzy Jeff & the Fresh Prince to a solo career that began in the late '90s. He would stay in the charts from their 1986 debut single, "Girls Ain't Nothing But Trouble," through to 1999's Willennium and beyond. As he continued to grow into an all-encompassing media personality, Smith remained sporadically active in music, releasing solo albums up until 2005's Lost and Found and making occasional guest appearances on tracks by Marc Anthony and Logic. Smith earned his first Grammy for the song "Parents Just Don’t Understand," which was also the first Grammy award for Best Rap Performance.