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7. 'Dick in a Box' (2006) by The Lonely Island
You start by cutting a hole in a box and take it from there. This hilarious sketch first featured on “Saturday Night Live” as a digital short forever sealed Timberlake’s fate as one of “SNL’s” all-time great hosts. He and Andy Samberg, performing as 2:30 AM, an white-boy R&B duo past its prime, have created this very special Christmas present because they’re, you know, “smart enough to know when a gift needs giving.” It’s either ridiculous or sublime that the song won an Emmy for Outstanding Original Music and Lyrics.