3. Dick in a Box
Original Airdate: December 17th, 2006
"[W]e wrote this song in a delirium of no sleep on a Wednesday or Thursday of the week. We recorded it that night, and we were laughing so hysterically – and probably through the delirium of trying to write something so funny, this came out of it," Justin Timberlake told NPR about co-writing the most popular SNL Digital Short of all time (and possibly the best Timberlake song post-FutureSex/LoveSounds). Though co-star Andy Samberg says this R-rated, very-bleeped send-up of '90s R&B was written in two hours, it's shelf life is seemingly endless – a performance at Madison Square Garden, an Emmy for Outstanding Music and Lyrics, two follow-up sketches, and a stardom for Samberg that continues today. "[Lorne Michaels] says the thing you're known for will be in quotes in the middle of your name," he told Esquire He's Lorne 'SNL' Michaels, and I'm Andy 'Dick in a Box' Samberg. If that's how it goes down, that will be A-okay."