26. Justin Timberlake – Cry Me a River
Say what you want about JT, but he is undeniably THE pop star of the '00s. And I think that is still kind of understating what he is. Like a said a couple months ago when I wrote about "My Love," JT is more than Michael Jackson 2.0. More artistically viable and soul-baring than The King of Pop EVER was, Timberlake occupies this weird modern airspace somewhere between Marvin Gaye and MJ. And, I know this could burn me in the end, but given a continuous steady progression over the next 40 years...I think Justin Timberlake is the next Frank Sinatra.
Yeah, that just happened. Ole' Blue Eyes. But think about it - hugely popular, ultra-accessible, identified with an entire generation of cool guys, smooth as fuck. Fantastic voice, fantastic presence, and the man can't do anything wrong when it comes to his image. Universally loved by hipster, hippies, hip-hop, everybody. Sounds like Frankie to me.
And "Cry Me a River" is the beginning. Yes, he was in N'SYNC. So? Aimee Mann was in 'Til Tuesday. Who gives a fuck? This is a monumental breakout, a giant leap forward, one small step for Timberlake, one giant leap for popular music in this country. You can't deny that this took us in a smarter, slicker, and goddammit COOLER direction altogether with our shitty mainstream pop. Even if you don't like the style, you knew for once there was some substance there.
The second best pure pop song of the decade. And at 3:39, when he slips a beat early into that crushing, piercing falsetto. That is, for my money, the number one moment in pop music in the '00s. Unbeatable.
(Apologizes to Timbaland. Amazing production, beginning of a new era of sounds, yadda yadda. Ran out of room.)
30. Elliott Smith – Son of Sam
I firmly believe that at any given time, there is one outright Best Singer-Songwriter in the World. Bob Dylan from 1963-67. Nick Drake from 1969-72. Bob Dylan again from 1975-76. Tom Waits from 1983-87. Jeff Buckley in 1994. Johhny Cash, Leonard Cohen, Neil Young. Sufjan Stevens from 2003-06. Probably Justin "Bon Iver" Vernon most recently.
And from, say, 1997-2000, Either/Or to Figure 8, Elliott Smith was the Best Singer-Songwriter in the World. "Son of Sam" is the Beatles-rollick swan-song of his pre-humous career, a Lennon/McCartney jaunt 35 years too late. Was it his strongest work? No. But it was the best we got in the '00s, and anything Elliott Smith released while breathing in this decade was a gift.
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