Found on: Saturday Night Live (2005 - 2009)
Picked by: KT, PA
This is a cheat of course, a way to get 3 songs for the price of one. I make no apologies.
The first is 2005's Lazy Sunday, a hard-hitting chronicle of two friends (Samberg and Chris Parnell) preparing to watch The Lion, the Witch, and the Wardrobe together and boasting about their Matthew Perry trivia knowledge.
For 2006's Dick In a Box Samberg got an upgrade in partners (Chris Parnell to Justin Timberlake is no contest) and parodied Color Me Badd in both style and substance. Any resemblance to a scene in Diner is purely coincidental.
Finally, 2009's I'm On A Boat found Samberg, Akiva Schaffer (who co-wrote the previous two songs as well), and T-Pain bragging about their nautical adventures. My favorite part is when an Autotuned T-Pain warbles dreamily, "I never thought I'd be on a boat."