The Lonely Island feat. Justin Timberlake – “Dick in a Box” – (2006)

Yeah, yeah. I know I always list the album release year as the date above, but because this was an SNL Digital Short in 2006, I listed it as that (the album came out in 2006). This was one of the biggest Digital Shorts they ever did. The song was recorded in one night and the music video shot in a day. SNL published the uncensored song online the day after it aired and it was a huge internet phenomenon. The song actually won an Emmy and the two characters that Andy Samberg and Justin Timberlake created for this song have made re-appearances, releasing two more songs. And yes, I know I’m at the bottom of the duet barrel.

#1 – Justin Timberlake – “SexyBack” – (2006)

It was this song (and this album) that told me that Justin Timberlake is going to be the biggest pop star in the world – and one that, so far, I respect. He is extremely talented – much more so than his NSYNC days would lead you to believe, with that curly bleached-blond weirdo hairdo. This song topped about every pop chart in the U.S. and many overseas. A lot of credit has to go to Timbaland – who owned 2006. He produced this album and co-wrote the song (and appears in it as well). I have zero doubt that this is the biggest song of the 2000s. It put J.T. on top of the world and he hasn’t left that position since. Thanks for following along!

#64 – Justin Timberlake – “Rock Your Body” – (2002)

As a Millennial, I witnesses music like this from inside the target demographic. And something weird happened around this time. This wasn’t necessarily the rule, but what I saw was that around 1999/2000 – the boy bands and girl groups and rock bands all had their own audiences. Girls loved NSYNC and boys thought Britney was hot but wouldn’t admit to liking her music – they preferred dumb, hard rock – because it was “music.” Well this was JT’s first solo album and this track was a solid hit (top five in the U.S.). But guys still wouldn’t admit to liking the music – this was just another NSYNC member who would have a brief solo career and disappear like Nick Lachey. Anyone who thought that about Timberlake was dead wrong (obviously) and his music has become more and more impressive as his career progresses. There will always be those who refuse to admit his talent – but he has a lot of it and this was just the start of him being able to showcase it.