Where did he come from?

Older readers might remember Justin Timberlake from the Mickey Mouse Club star incubator that also housed the embryonic Britney Spears, Christina Aguilera and JC Chasez. But most of us were introduced to JT through his boy band N' Sync.

You mean like the Backstreet Boys?

Pretty much exactly like the Backstreet Boys. Oh, there were differences—any kid at the time could rattle off twenty in a second. But the basic formula was the same: five guys, Max Martin songs, synchronized dancing and massive sales. No Strings Attached was the second-best selling album of the decade. N' Sync also had what Backstreet lacked: a breakout star. Boy band members play strict roles—a concept skewered by MTV draftees 2get+her, with explicit roles like The Bad Boy and The Older Brother. JT, much like peer Nick Lachey, was the heartthrob. Modern oglers might be skeptical about his frosted tips, cornrows and dry-ramen hair, but to girls back then, they were the swoonworthy, if creatively styled, locks of an Adonis. Nobody even came close. Unfortunately for them, though, dude was taken by Britney Spears.

That’s quite the pairing.

It truly was: teen-pop’s newly crowned royalty united in the perfect, virginal (or so they said) pairing that was the implied endpoint of all their love songs. Almost no matchup in today’s pop landscape could come close.

But were they really virgins?

No way. The whole virginity thing was designed to make them better role models, both for parents and listeners. Is your boyfriend pressuring you into sex? Don’t worry; Britney and Justin are just like you! Except they weren’t, and after the whole charade became ridiculous, the couple admitted they’d been sleeping together for some time. Which is fine; it’s totally okay not to be a virgin just as it’s totally okay to be one, and the fixation on stars’ virginity is one of the uglier spots on America’s gossip-cultural underbelly.

Speaking of the gossip-cultural underbelly, wasn’t their breakup pretty bad?

It was, even by celebrity standards. After three years, rumors surfaced that Britney had cheated with choreographer Wade Robson. Britney went on to date, um, Kevin Federline and Justin, evidently hurt, cast a not-so-subtle lookalike in his single “Cry Me A River” (sample lyric: “You don’t have to say what you did / I already know / I found out from him”) and rehashing the theme in follow-up “What Goes Around… Comes Around." But Timberlake also dated Fergie, Alyssa Milano, Cameron Diaz, Jessica Biel and probably countless other ladies we don’t know about, so all things considered, he came out okay.

So about this solo career. When did it start?

In 2002, Timberlake released his first solo album Justified, selling millions and shocking the world with the revelation that this boy-band kid was actually kind of good! Not that he wasn’t before; Justin had always brought steam and swagger to his work, even if said work involved being jerked around by marionette strings. But Justified suggested a new role model: Michael Jackson. Okay, nobody can be the King of Pop, but JT’s voice and moves made him at least an earl. He even duetted with Janet on the flirty "Rock Your Body”—yes, the song responsible for the Nipplegate fiasco at the Super Bowl. He apologized, of course, and the incident actually helped listeners distance him from his past. It also helped that JT upgraded his relationship with Timbaland from sometime producer to longtime collaborator.

Timberlake and Timbaland, that’s funny!

It’s also kind of telling; the two belong together. Much like Nelly Furtado and the late Aaliyah, JT spurred Timbo to produce some of his best work. In Justin’s case, it was the multi-platinum FutureSex/LoveSounds, a synthy breakthrough of an album with singles like "SexyBack,” which turns robot lurching into seduction, and the sumptuous “My Love,” featuring T.I. Justin provided a versatile, falsetto-streaked canvas for Timbo’s songcraft, and Timbaland allowed Justin to become what he’d always aspired to be: a credible R&B star. (As for “Carry Out,” well, everyone screws up sometimes.)

Wait, FutureSex/LoveSounds was 2006. What’s up with the hiatus?

It wasn’t exactly a hiatus; guest spots with Timbaland, T.I. and Ciara meant Justin’s voice never really went away. But there hasn’t been much solo work yet—he announced at the Oscars that he was planning on getting back into the studio soon, but then again, he also announced at the Oscars that he was Banksy.

Don’t you mean the Grammys?

No, we mean the Oscars. For acting. JT’s a funny guy, albeit in a bro-ish way, so it’s not surprising that he dabbles in TV comedy. He appeared on Ashton Kutcher’s Punk’d as both pranker and prankee and with Andy Samberg, played the, um, title role in SNL’s viral sketch “Dick in A Box” and its sequel “Motherlover.” Not that Timberlake doesn’t do Serious Films too. Sure, he’s only an “actor” insofar as he plays young guys not too far off from himself—young Napster entrepreneur Sean Parker in The Social Network, gang member in Alpha Dog and everydude Dylan in the upcoming Friends with Benefits, to name a few. But hey, he’s pretty.