Year: 2006
Director: Akiva Schaffer

Who knew Justin Timberlake was funny? This video cemented the singer as Andy Samberg's go-to guy for SNL's Digital Shorts, and let him co-star in "Mother Lover" and pop up in "Jizz in My Pants" shortly thereafter. And come on, who didn't attempt this as a gag gift that holiday season? Hahahaha, "gag gift."

In 2007, the song won a Creative Arts Emmy for Outstanding Original Music and Lyrics.

Also Watch