Air Date: Dec. 16, 2006
Starring: Justin Timberlake, Andy Samberg
While Pharrell Williams' willingness to take Justin Timberlake under his wing lead to the 2002 image resurrection and musical comeback of the century, it was the former 'NSyncer's guest hosting spot on SNL that made just about the entire country bow down to the guy's undeniable flair for comedy. Paying homage to corny R&B videos of the past, the star's digital short with Andy Samberg features two chin-strapped crooners expressing exactly how they'd like to show their ladies the holiday love—by presenting them with the ultimate Christmas package (literally): A dick in a box.
Dudes can hate on Justin all they want, but the numbers don't lie. The edgy video tested the series' limits and the payoff was huge: It became one of the biggest viral sensations on the Internet, raking in millions and millions of views on YouTube—and that's only the official vid. In addition to inspiring countless T-shirts, Halloween costumes, and, presumably, sexual harassment suits, the X-rated Christmas carol was honored with an Emmy Award for Outstanding Original Music and Lyrics, giving it further bragger's rights of being the first (and likely only) honoree to force a presenter to utter the word “dick” at the otherwise classy ceremony. For all the fellas out there with ladies to impress, it's easy to do; just follow these steps.