“Dick In A Box” by The Lonely Island feat. Justin Timberlake (2006)

I don’t think “Dick In A Box” is as good without its video accompaniment. However, the song still works really well as a parody of ‘90s R&B. While Michael Jackson is and has always been JT’s primary influence, you can listen to his catalog and hear lots of Boyz II Men and Brian McKnight influences as well. It’s pretty clear that in between the time he did his cowboy schtick on Star Search and the time *NYSNC blew up, Justin spent quite a bit of time soaking up black radio. And that time period syncs up pretty well to the “freaky R&B” era of the early ‘90s. Thinking about that makes the line even more blurry between this obvious parody and songs like “Freak Me” and “Downtown”, which were deadly serious but had lyrics that were almost just as laughable in their outsize sexuality.

While JT is cool, and Andy Samberg is tolerable to me in small doses, I have to give the biggest props to Katreese Barnes, the co-writer of “Dick in a Box” and unsung hero of many of these mid-2000s SNL bangers. Katreese was half of one-hit wonder R&B duo Juicy and went on to become the musical director for Rosie O’Donnell’s ABC talk show and eventually got hired as Saturday Night Live’s musical director (which deserves as many props as you can muster up, given how difficult it is for sistas to get this far up the ladder even today).

This video, though. This might’ve been the first viral SNL clip that I literally got up the next morning and emailed to all my friends. I used this song as my ringtone for months on end. Still cracks me up.

The video’s not on YouTube, but you can watch it in all its gloriousness here.


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