By James Pavel

5. Not such a Bad Thing

Leave it to JT to recognize that instead of saturating the radio with a lethargic EDM fist-pumper, he releases a throwback to the N Sync*/BSB domination days, where falling in love to pop songs happened every music video. He hasn’t forgotten his roots, except maybe the macaroni curls and full-piece denim suits. He is a mainstay on late night television and sometimes stars in the year’s biggest films but this hasn’t stopped him from writing songs about everyday implications that Not Such a Bad Thing discusses.

4. Love Stoned/I Think That She Knows

LoveStoned served as space-age lust for millennials and generation-Xers. The opening four minutes is future-fabulous, but it’s the final two minutes that unwind into something as revealing as a sudden black hole. “I think that she knows,” is always supposed to be bad, but really it is marvelous news, as it allows the chance for something to happen that wasn’t previously possible.

3. Mirrors

Audiences have listened for decades about what he desired, what he craved, and what he lusted over. Mirrors is a parade dedicated solely to Jessica Biel with Justin clinking his glass to make his grandest toast to his most precious feat. The chorus is less a poppy hook and more modern-day wedding vowels, which would be a tiring ordeal for fans if it wasn’t anybody besides JT. Timberlake is simply one of the most likable entertainers in history. He can act, he can dance, he can obviously sing, and he can marry women that look like Jessica Biel.

2. Sexy Back

It didn’t sound like Timberlake. We initially refused to believe he could conceive something so radical sounding. And yet, the radio host did not lie. Timberlake had brought back what we didn’t know had gone missing, and if you didn’t like him before, you did the moment you walked into the club Friday night. It was aggressive and naughty, but not soulless or exploitive. JT made a song that no one has dared to make before or after and it remains a staple of modern-day dance-club mayhem.

1. Cry me a River

To make a villain likable, you must find a way for the audience to empathize. Men were reluctant to accept Timberlake had talent, even despite their girlfriends and crushes relentless claims that a new King of Pop was performing right before us. His first solo single, The Way I love You, was swanky, but it still didn’t exactly force dudes to allow room for a new king on the throne of Michael Jackson. But when he sat us down through a rain storm and told us how Britney Spears, our collective love interest, had cheated him, we began to finally listen. The hypnotic Timbaland beat-box beat paired with Justin’s cryptic accusations, made the old-idiom, cry me a river, a revived chant for those cheating lovers spewing crocodile tears.

Usher laid claim to the throne early on, but couldn’t help be seduced by the easy money that dance music offered. JT always refused. He has always seemed to search for a way to push music to previous unknown realms, while maintaining a chokehold on pop culture’s pulse.