To understand the appeal of Justin Timberlake, I recommend listening to his record.
Even in my Alternative Nation teenage years I could tell that *NSync were much better than the Backstreet Boys. “Bye Bye Bye” had much more pep and verve than its Backstreet analogue, “Backstreet’s Back,” and the ballad “Gone” had an R&B edge that the Boys ballads never hinted at. And of *NSync, Justin was the clear star.
He made the transition to solo act well, both in terms of artistry and career management; his debut single, “Like I Love You” had a hot Neptunes beat and a guest verse from the Clipse, a Virginia rap duo that raps almost exclusively about dealing coke (they’re The Wire recast as a hip hop act). He could have collaborated with Nelly, a far more pop-oriented Neptunes affiliate who would have been much more recognizable to his audience and far less risky. Instead, he chose the respected street act, and it paid off - “Like I Love You” had just enough thug in it to drag Timberlake out of the boy band for good.
His debut, Justified was solid and wore its Michael Jackson influences on its sleeve. But if you’re going to claim yourself as a modern day Michael, then you need the songs to back it up, and Justified delivered these in spades, from the disco of “Rock Your Body” to the operatic overtones of “Cry Me A River.”
Having staked out a claim as a legitimate pop star, he used FutureSex/LoveSounds as his bid for importance. This album is best heard in full - there are interludes, tracks that work to sustain the mood and flow, and an overarching asthetic that isn’t quite communicated solely by listening to the singles. It’s the sort of album that is greater than the sum of its parts, the compelling work of a pop star pushing the envelope. He introduced a lot of Prince influence on many of these tracks, and that seems to be his intended career arc; having established himself as a legitimate pop star, he wants to establish himself as a legitimate artist.
This is one of the interesting things about Timberlake. He is always pushing his music one step beyond what it needs to be. His debut didn’t need to be anywhere near as good as it was; he could have coasted on his boy band wave and got healty sales simply because he was Justin. But if he’d done that we’d have forgotten all about him by now; he went the more difficult route and was rewarded with a career. It was the same with his second album. Having comfortably worked his way into Usher-style R&B pop singer niche, he could have served up more of the same and done well for himself. Instead he worked mostly with one producer to make a record with a cohesive, innovative sound, and as a result, he’s turned himself into something approaching an artist. In the interviews leading up to the release of FS/LS, he’d invoke names like David Byrne, and although he may not be at Talking Heads level, it’s important that he was aiming for that.
The OP described his singing as unexceptional, which sort of misses the point. Timberlake’s voice isn’t fantastic, but he uses it well. That sort of thin tenor (or whatever it is - I’m not good at vocal terminology) could easily get lost and anonymous in the middle of a pop song, but Timberlake instead gets it to float ethereally above the busy beats and clicks Timbaland conjures for him. Listen to “My Love” - the vocal performance isn’t anything to write home about in itself, but the way it interplays with the trance synthesizer is something very special. And Timberlake performs the song well - his phrasing, his delivery - it all goes into making his uninteresting lyrics much better than they should be.
You should also remember that having a good voice and making good music are two very different things. Take American Idol, for instance, which spends weeks getting contestants to show off their vocal gymnastics, apparently under the theory that procuring a talented vocalist is the most necessary step to procuring a good pop song. In real life though, once the show is over, the Idol flounders because he or she has been selected on their voice rather than their ability to so good music. It’s telling that the Idol winners who have gone on to success did so with songs that didn’t need a good voice to perform. Kelly Clarkson had hits because she had well written songs, not because they were particularly difficult to sing. Likewise, Carrie Underwood, though she can belt out a country tune, has benefited more from her ability to give a believable performance than a technically accomplished one. Timberlake’s vocal ability is not important, it’s his performing ability that is behind is success.
You could suggest that he merely has benefited from working with talented collaborators, and while it’s true he has worked with the best, he should not be dismissed as a puppet. Timbaland, for instance is very talented, but with the wrong talent he can turn out uninpired to middling work. Justin complements him in a way few singers have since Aaliyah, and their relationship has Timberlake as a collaborator rather than a marionette.
