The foundation of Justin Timberlake's fame--broad-based and consistent and weirdly resistant to automatic internet backlash--is that it came, originally, from looking this ridiculous, and he seems to accept that. That's the only thing I can come up with to explain just how many people I heard talking about his appearance on Saturday Night Live over the weekend. People I hadn't seen since high school showed up unannounced on my Facebook news feed, anticipating it; friends took the opportunity to remind me that they didn't own TVs but kind of wanted to see it; my mom DVR'd it.
People like Justin Timberlake because he is a cool musician who realizes he was not always cool. On SNL he de-escalated one of the least-threatening music beefs of the last 20 years by casually responding to Kanye West's public distaste for "Suit and Tie." That he dismissed a 10-minute freestyle-rap diss with two jokey lines is exactly the sort of thing that makes Kanye West furious enough to write 10-minute freestyle-rap disses. It's exactly what makes Justin Timberlake beloved and Kanye West a cartoon character.
Full disclosure: I prefer Kanye West to Justin Timberlake, and have since The College Dropout. I've got a soft spot for "Suit and Tie," but Kanye's been a remarkably inventive rapper and producer across five (and change) albums, and while I might prefer "Heard 'Em Say" to "Monster" it's to his credit that the same guy created both of them.
And it's not that Justin Timberlake hasn't embarrassed himself in the past, at least in front of those of us who were unfortunate enough to watch Alpha Dog.
But what Justin Timberlake has never done--and yes, I'm oversimplifying here, because he also hasn't called a president racist, or interrupted Taylor Swift, or otherwise looked like a lunatic on TV--is labor in front of us. That's why SNL is his medium. SNL is written and rehearsed meticulously by people who forego sleep and fame to build a better Obama joke, but it only works when it looks like the actors are coming up with things on the spot, casually, like they've just thought of something funny.
Here is Kanye West trying to act casual, and spur-of-the-moment, and unlabored:
It doesn't work. He looks like he's spent three weeks holed up in a Method workshop, trying to become Jay-Z's handsy younger brother. Justin Timberlake can make goofy songs with Andy Samberg and perform them while staying in on the joke; Kanye West only looks comfortable when he's committing fully to having sex with a bird-lady, or appearing in a live-action Akira, or being decapitated.
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As fans of music--and musicians--most of us want to identify with what looks effortless. Effortless is John Lennon tearing his own throat out performing "Twist and Shout," labored is Paul McCartney doing "Beware My Love" with Linda on backing vocals. Effortless is Jay-Z releasing another album about being absurdly rich that makes him absurdly richer; labored i Kanye West releasing an album called My Beautiful Dark Twisted Fantasy because that's exactly what it is, and he spent months making it that way.
It's probably unfair, and it's definitely missing something fundamental about popular music--the baroque, unhinged tradition that contains Brian Wilson and Michael Jackson and Kanye West, eventually turning in on itself and producing Love You and Invincible but not before Pet Sounds and Thriller.
But it's just how we wish we were--and so much of what connects us to music at first is wish-fulfillment. We want to look like we were born in a suit and tie, not like we spent two weeks on a private jet looking for the right kilt. We don't want to sit in the studio overdubbing a million vocal takes; we just want to perform "All Of The Lights."