Justin Timberlake

Few teen idols have made the transition to adult pop star quite as seamlessly as Justin Timberlake, whose 2002 solo debut, Justified, remains the model for every former boy-band kid looking to rebrand himself. For his most recent solo event, Man of the Woods, Timberlake recruited tried-and-true collaborators like Timbaland and The Neptunes while also expanding his sound, dabbling in country a bit and even sharing a duet with Chris Stapleton on the single “Say Something.” That song’s success teases a possible direction for Timberlake on future albums: more flannel, less dancing.