You’ve gotta wonder how Justin Timberlake does it. Star Search, The Mickey Mouse Club, teen-pop pinup, making the leap from boy to man and sticking the landing without a squeak. A deadpan loverman working at the vanguard of pop and R&B, yes, but also a member of the Five-Timers Club on Saturday Night Live and a regular voice in kids’ movies—the artist who never takes his eye off the show. The best tracks here aren’t just good pop (though they are that), they’re cultural barometers, a map of the ground pop has covered during the 2000s and 2010s. From the futuristic to the charmingly retro, the dance-floor fillers to the windswept ballads, here’s the best of JT.