Lists \

Mr. Motherlovin’ Esquire: The History of Justin Timberlake’s Hip-Hop Cred

History of Rap Parts 1-24

Justin Timberlake’s decade-long dalliance with rap has been a slow crescendo, yielding multiple collabos that would have been downright impossible in the frosted tip of the ’90s. It’s a willingness to take risks — putting the Clipse on his debut solo single, teaming with Three 6 Mafia on an album cut, uh, doing the Crip Walk onstage — that turned JT from pop’s ultimate rap stan to one of the most wanted hooksmiths in the game. On the cusp of his stadium tour alongside Jay-Z, we look back at how our dapper friend went from Mouseketeer to hip-hop heavyweight. Let us show you a good thing.