Samberg sings that he's "king of the world, on a boat like Leo" referring to Leonardo DiCaprio in the movie Titanic, and mentions Kevin Garnett's 2008 NBA championship finals victory quote "anything is possible".

After pondering who will go with him, Samberg picks Schaffer but overlooks Taccone in favor of the previously unseen R&B singer T-Pain, who has apparently been sitting at the table, off camera, the entire time.

The video frequently shows scenes of the left-out Taccone at comparatively mundane places, for example, "at Kinko's straight flippin' copies", taking out the trash, or lifting a parking ticket from his car.

The rap portion of the video places Samberg, Schaffer and T-Pain throughout the boat and in varying attire, including a flight suit (parodying George W. Bush's 2003 Mission Accomplished speech), traditional sailor costumes, white naval uniforms, "a nautical-themed pashmina afghan" and typical casual and formal resort wear.

T-Pain recounted that the helicopter used to take the aerial shots, combined with the cool breeze, was "spraying so much water on us" that it made for "probably the worst video day I've ever been through".

[6] Giving the song four stars, Rolling Stone said it is "one of the strongest Saturday Night Live hip-hop hits since Eddie Murphy was funny.

[15] T-Pain called back to the song on The Masked Singer when he was The Monster, With his "revealing clue" being "I got the music, the lyrics, and the cadence to take them down—whether it's in my cave, at the bar, or on a boat."

The multiplayer online battle arena video game League of Legends released a 2009 April Fool's Day teaser for a joke manatee champion named Urf.