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.