The song features an aggressive delivery of the lyrics which are peppered with strong profanity throughout while making simple proclamations, ranging from the mundane ("The boat engine make noise") to the insane ("I'm gonna fly this boat to the moon somehow"). Schaffer at one time claims to be riding a wild dolphin, and doing flips, and at another time to be climbing buoys. 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".
The video opens with Andy Samberg — who is sitting at the kitchen table with bandmates Akiva Schaffer and Jorma Taccone — pouring cereal into a bowl. To his delight, a coupon for a free boat ride for three falls out of the box. After pondering who will go with him, Samberg picks Schaffer but skips over 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 three men are next seen atop the yacht Never Say Never in Biscayne Bay, Florida, dressed in tuxedos as Samberg announces that they are about to set sail on a boat. The video frequently shows flashes of the left-out Taccone at comparatively mundane places, like "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 the three throughout the boat and in varying attire, including full tuxedos, a flight suit (parodying George W. Bush's 2003 Mission Accomplished speech), traditional sailor costumes, white naval uniforms, "a nautical-themed pashminaafghan" and typical casual and formal resort wear.