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“I’m on a Boat” is a single from The Lonely Island’s debut album Incredibad, and was also featured as a Saturday Night Live Digital Short. The song features R&B singer T-Pain. The song, produced by Wyshmaster, is a parody of many rap video cliches. The music video reached number one on YouTube in February 2009 and was number one on the U.S. iTunes music video chart. The Lonely Island has also performed the song live on Late Night with Jimmy Fallon with The Roots filling in for T-Pain. 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 singer 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.