6. I’m on a Boat (2009)
A popular Lonely Island sketch featuring T-Pain, "I’m on a Boat" captures Samberg and co. partaking in the experience of a lifetime. “I’m on a boat” is a phrase that has come to mean so much more than the literal vessel that keeps you afloat on the water. Saying, “I’m on a boat” is akin to stating that one is “king of the world,” according to the song’s lyrics. The song and sketch was such a big deal that it was nominated for a Grammy, “Like a Boss.” (See #2)
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