24. Postal Service – Such Great Heights
Forget what the song sounds like now. Nevermind that it holds up aesthetically thematically and technologically like it came out last week. Without this song, music would flat out be different right now. Indie, alternative, radio rock. Ben Gibbard's main squeeze may be Death Cab, but the fling he had with Jimmy Tamborello in 2003 is his most influential contribution to music.
Since then, everything has been just a little more electronic, a little more burble-y, alternative music a little less ashamed of being overtly pop or poppy music unafraid to be a little obtuse. No one will admit it, but Such Great Heights helped create the late '00s hipster popularity movement as much as any song on Earth. God dammit Ben.
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.)