"I'm on a Boat" SNL Digital Short
From The Lonely Island's album Incredibad.
Samberg wins a prize from a cereal for a boat trip for three and selects himself, Akiva Schaffer and surprisingly, T-Pain while Jorma Taccone stays out of the excitement. Then the group proceeds into a highly aggressive, profane rap song about sailing on a boat. The second single from the Lonely Island's debut album 'Incredibad'.
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 (Kiv) but skips over Taccone in favor of the previously unseen rapper T-Pain.
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" 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, traditional sailor costumes, white naval uniforms and typical casual and formal resort wear. The song features an aggressive delivery of the lyrics which are peppered with strong profanity throughout while making simple proclamations, ranging from the ridiculous ("I'm riding on a dolphin") to the mundane ("I've got a nautical-themed pashmina afghan") to the inane ("The boat engine make noise"). The video concludes with a wide shot of the entire boat.
The song and video parody the opulence and profanity typically flaunted in popular rap videos. Billboard said the song "takes hip-hop boasting to its most absurd extreme," while the New York Times called it a "sendup of triumphant materialism." The parody is extended in the inclusion of T-Pain, known to sing the hook line in many rap songs, with his trademark overuse of auto-tune. Additionally, the video's intro resembles that of Akon's "I'm So Paid" video, especially the scene in which Akon is standing on the front of the boat.
The song makes allusions to various events, people and other elements from pop culture. The song quotes Kevin Garnett as saying "Anything is possible!" — an exclamation he made after the 2008 NBA Finals. Samberg visually and lyrically references Leonardo DiCaprio's scene in the 1997 film Titanic, where on the bow of the ship, DiCaprio's character shouts, "I'm the king of the world." In the video, Samberg holds a press conference with a blue "I'm on a Boat" banner in the background while wearing a flight suit, a sight gag reminiscent of President George W. Bush's 2003 "Mission Accomplished" press conference. Rapper E-40 (who appears elsewhere on the album) often mentions liquors in his rap, which corresponds to the mention of Santana champagne (the actual topic of E-40's featured appearance). Also, the final line that T-Pain hums is the hook from his 2007 song, Buy U a Drank.